[ CAS No. 4522-35-4 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 4522-35-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 4522-35-4 ]

SDS Specification

Alternatived Products of [ 4522-35-4 ]

Product Details of [ 4522-35-4 ]

CAS No. :	4522-35-4	MDL No. :	MFCD12022324
Formula :	C₃H₃IN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RUKDVLFJSMVBLV-UHFFFAOYSA-N
M.W :	193.97	Pubchem ID :	1239830
Synonyms :

Calculated chemistry of [ 4522-35-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	6
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	31.3
TPSA :	28.68 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.84 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.92
Log Po/w (XLOGP3) :	0.9
Log Po/w (WLOGP) :	1.01
Log Po/w (MLOGP) :	0.61
Log Po/w (SILICOS-IT) :	2.24
Consensus Log Po/w :	1.14

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.23
Solubility :	1.15 mg/ml ; 0.00594 mol/l
Class :	Soluble
Log S (Ali) :	-1.09
Solubility :	15.9 mg/ml ; 0.0818 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.19
Solubility :	1.26 mg/ml ; 0.00649 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.1

Safety of [ 4522-35-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 4522-35-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 4522-35-4 ]
Downstream synthetic route of [ 4522-35-4 ]

[ 4522-35-4 ] Synthesis Path-Upstream 1~1

1
[ 4522-35-4 ]
[ 74-88-4 ]
[ 92525-10-5 ]

Reference： [1] Synthesis, 2002, # 11, p. 1509 - 1512
[2] Patent: WO2007/35309, 2007, A1, . Location in patent: Page/Page column 62-63

[ 4522-35-4 ] Synthesis Path-Downstream 1~12

1
[ 111505-88-5 ]
[ 4522-35-4 ]
[ 111506-00-4 ]

Reference： [1]Tetrahedron Letters,1987,vol. 28,p. 3179 - 3182

2
[ 141998-84-7 ]
[ 4522-35-4 ]

Reference： [1]Heterocycles,1992,vol. 33,p. 813 - 818

3
[ 1820-80-0 ]
[ 4522-35-4 ]

Yield	Reaction Conditions	Operation in experiment
		Example 4N-(4-[l-(l-methyl-lH-pyrazol-3-yl)-lH-indol-5-yl]oxy}rhoyrintauidin-2-yl)benzene-l,3-diamine (Compound 75)Scheme 4Step 1: 3-iodo-lH-pyrazole.To a stirred suspension of lH-pyrazol-3-amine (1.0 g, 12 mMol) in concentrated HCl (16 mL) was added a solution of sodium nitrite (1.7 g, 24 mMol) in water (3.0 mL) over 5 minutes at 00C. To the resulting orange reaction mixture was added a solution of KI (5.0 g, 30 mMol) in water (7.0 mL) over 10 minutes, resulting in nitrogen evolution. The reaction mixture was stirred for 5 minutes, upon which nitrogen evolution ceased. TetaF (25 mL) was added, followed by water (25 mL). The aqueous mixture was extracted with Et2O (3 x 30 mL) and the combined organic extracts were washed with Na2S2O3 (2 x 30 mL), dried over magnesium sulfate, filtered and concentrated to afford the title compound. LRMS (ESI) calculated for C3H3IN2 [M+HJ+, 194.9; found 194.9.
	With hydrogenchloride; potassium iodide; sodium nitrite; In water; at 0 - 28℃; for 2.75h;	To a stirred suspension of 118 (2.00g, 24.O7mmol) in concentrated HC1 (32mL) was added a solution ofNaNO2 (3.32g. 48.i4mmoi) in water (5mL) over 5 minutes at 0C. To the resulting orange reaction mixture was added a solution of KI (9.99g, 60 iSmmol) in water (l0mL) over 10 minutes. The reaction mixture was stirred at 0C for 30 minutes and then kept at 28C for another 2 hours, TLC showed the reaction was complete, then, solvent THF (3OmL) was added,followed by water (3OmL). The aqueous mixture was extracted with EtOAc (3 x8OmL) and the combined organic extracts were washed with Na2S2O3 (2 x4OmL), dried over Na2SO4, filtered and concentrated in vacuum to afford product 180 (200 g, crude), the crude product was used directly for the next step without purification.LCMS: m/z, i94.9M+H)??.

Reference： [1]Patent: WO2007/35309,2007,A1 .Location in patent: Page/Page column 62
[2]Patent: WO2017/117708,2017,A1 .Location in patent: Page/Page column 95

4
[ 402-44-8 ]
[ 4522-35-4 ]
[ 1164166-10-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 2h;	A mixture of <strong>[4522-35-4]3-iodopyrazole</strong> (prepared as described in WO2007/035309) (1.0 g, 5.1 mmol), 4-fluorobenzotrifluoride (0.72 mL, 5.7 mmol) and potassium carbonate (0.93g, 6.7 mmol) was stirred in lambda/,lambda/-dimethylformamide (10 mL) at 100 0C for 2 h. The mixture was diluted with water (60 mL) and extracted with ethyl acetate (2 x 30 mL). The organic layers were combined, dried over magnesium sulfate and concentrated. The residue after evaporation was subjected to silica gel chromatography (40 g silica) using a gradient of ethyl acetate/chlorobutane (0:100 to 50:50), and appropriate fractions were combined and evaporated to give the title compound (1.27 g). 1H NMR (CDCl3) delta 7.79 (m, 3H), 7.71 (m, 2H), 6.67 (d, IH).

Reference： [1]Patent: WO2009/86041,2009,A1 .Location in patent: Page/Page column 42

5
[ 446-33-3 ]
[ 4522-35-4 ]
3-iodo-1-(3-methyl-4-nitrophenyl)-1H-pyrazole [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 11628 - 11631
Angew. Chem.,2013,vol. 125,p. 11842 - 11845,4

6
[ 4522-35-4 ]
[ 882679-40-5 ]
[ 1533442-82-8 ]

Yield	Reaction Conditions	Operation in experiment
41%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 90℃; for 18h;Inert atmosphere;	Compound 51.1. Methyl 4-methyl-3-(lH-pyrazoI-5-yl)benzoate. To methyl 4- methyl-3-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl)benzoate (compound 5.4, 800 mg, 2.9 mmol) in dioxane (30 mL) was added 5-iodo-lH-pyrazole (674 mg, 3.5 mmol), and Pd(dppf)Cl2 FontWeight="Bold" FontSize="10" DCM (237 mg, 0.29 mmol). The mixture was degassed with argon and stirred for 10 minutes then an aqueous potassium carbonate solution (2 M, 8 mL) was added. The mixture was heated at 90 C for 18 h, then cooled and diluted with EtOAc and filtered through Celite. The filtrate was washed with brine, dried (MgS04), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (Si02; 0-30 % EtOAc in hexanes) to yield 258 mg (41 %) of the title compound as a solid. m/z
41%		Compound 51.1. Methyl 4-methyl-3-(lH-pyrazol-5-yl)benzoate. To methyl 4- methyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzoate (compound 5.4, 800 mg, 2.9 mmol) in dioxane (30 mL) was added 5-iodo-lH-pyrazole (674 mg, 3.5 mmol), and Pd(dppf)Cl2 DCM (237 mg, 0.29 mmol). The mixture was degassed with argon and stirred for 10 minutes then an aqueous potassium carbonate solution (2 M, 8 mL) was added. The mixture was heated at 90 C for 18 h, then cooled and diluted with EtOAc and filtered through Celite. The filtrate was washed with brine, dried (MgSC^), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (S1O2; (M0-30 % EtOAc in hexanes) to yield 258 mg (41 %) of the title compound as a solid, m/z (ES+) 217 (M-H)+

Reference： [1]Patent: WO2014/8197,2014,A1 .Location in patent: Page/Page column 120
[2]Patent: WO2015/95767,2015,A1 .Location in patent: Page/Page column 135; 136

7
[ 18997-19-8 ]
[ 4522-35-4 ]
[ 1616070-60-0 ]

Yield	Reaction Conditions	Operation in experiment
		3-Iodo-1H-pyrazole (19.44 g, 100 mmol) was charged to a flask followed byTHF (237 mL) and the solution was cooled to -10 C. NaH (4.41 g, 110 mmol)was added in portions keeping the internal temperature below -10 C. Thereaction was stirred for 30 min, then chloromethyl pivalate (17.45 mL, 120mmol) was added and the reaction was stirred for 1 h at -1 0 C and then allowedto warm to room temperature. The reaction was cooled in an ice bath andquenched with sat. NH4Cl then diluted with EtOAc and water. The organiclayer was washed with brine, dried over MgS04 and the solvent was removed.The product was purified by flash chromatography eluting with 0-50%EtOAc/hexane to give (3-iodo-1H-pyrazol-1-yl)methyl pivalate, as a white solid.LCMS calc.= 309.01; found= 308.87 (M+H+).
		3-Iodo-lH-pyrazole (19.44 g, 100 mmol) was charged to a flask followed by THF (237 mL) and the solution was cooled to -10 C. NaH (4.41 g, 110 mmol) was added in portions keeping the internal temperature below -10 C. The reaction was stirred for 30 min, then chloromethyl pivalate (17.45 mL, 120 mmol) was added and the reaction was stirred for 1 h at -10 C and then allowed to warm to room temperature. The reaction was cooled in an ice bath and quenched with sat. NH4C1 then diluted with EtOAc and water. The organic layer was washed with brine, dried over MgS04 and the solvent was removed. The product was purified by flash chromatography eluting with 0-50% EtOAc/hexane to give (3-iodo-lH-pyrazol-l-yl)methyl pivalate, as a white solid. LCMS calc. = 309.01 ; found = 308.87 (M+H+).
		Step A: (3-Iodo-lH-pyrazol-l -yl)methyl pivalate To a solution of <strong>[4522-35-4]3-iodopyrazole</strong> (1.40 g) in THF (25 mL) was added NaH (0.32 g, 60%wt) at 0 C. After stirring for 10 min at 0 C, chloromethyl pivalate (1.14 g) was added to the reaction at the same temperature. The reaction mixture was stirred for 1 h at room temperature. It was diluted with sat. NaHC03 aq. and extracted with EtOAc (2 times). The combined organic layer was washed with brine, dried over Na2S04, filtered and concentrated to give (3-iodo-lH-pyrazol-l -yl)methyl pivalate, as a brown oil, which was used in the next step without further purification. LCMS 331 (M+Na)+. NMR (300 MHz, CDC13): 5 7.48 (1 H, d, J= 2 Hz), 6.45 (1 H, d, J= 2 Hz), 5.97 (2 H, s), 1.17 (9 H, s).

Reference： [1]Patent: WO2014/99695,2014,A1 .Location in patent: Page/Page column 62
[2]Patent: WO2014/99694,2014,A1 .Location in patent: Page/Page column 107; 108
[3]Patent: WO2014/120346,2014,A1 .Location in patent: Page/Page column 98

8
[ 1220039-64-4 ]
[ 4522-35-4 ]
[ 1616069-42-1 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of<strong>[4522-35-4]3-iodo-1H-pyrazole</strong> (0.75 g) in DMSO (19 mL), was added60% NaH (0.39 g) under ice cooling and stirred for 10 min. 4-bromopyridazinehydrobromide (1.4 g) was added and stirred at room temperature for 3 days.Then 60% NaH (0.16 g) was added at 0 OC and warmed to room temperatureand stirred for 1 day. The reaction mixture was diluted with water and EtOAc. The mixture was filtered with Celite, and extracted with EtOAc. The combinedorganic layer was washed with brine and dried with anhyd. Na2S04. It wasfiltered to remove insoluble matters and it was concentrated in vacuo. Theresidue was triturated (Hexane:EtOAc= 1:1) to obtain compound 2-1 as a brownsolid.

Reference： [1]Patent: WO2014/99695,2014,A1 .Location in patent: Page/Page column 37; 38

9
[ 96530-81-3 ]
[ 4522-35-4 ]
[ 1350475-30-7 ]

Yield	Reaction Conditions	Operation in experiment
		To <strong>[4522-35-4]3-iodo-1H-pyrazole</strong> (763 mg, 3.93 mmol) in DMSO (15 mL) at 0 oc, wasadded sodium hydride (60% in mineral oil, 189 mg, 4.72 mmol). The reactionwas warmed to 25 C and stirred for 60 min before 4-fluoro-2-methoxypyridine (500 mg, 3.93 mmol) was added. The reaction mixture was stirred at 90 C for4.5 h before quenching by the addition of water. The reaction mixture wasextracted with EtOAc. The combined organic extracts were dried over MgS04and concentrated in vacuo. The crude mixture was purified by flashchromatography (ISCO Combiflash, 0-30% EtOAc in hexanes) to afford 4-(3-iodo-1H-pyrazol-1-yl)-2-methoxypyridine, as a white solid. LCMS calc.=301.97; found= 302.02 (M+Ht
		To 3-iodo-lH-pyrazole (763 mg, 3.93 mmol) in DMSO (15 mL) at 0 C, was added sodium hydride (60% in mineral oil, 189 mg, 4.72 mmol). The reaction was warmed to 25 C and stirred for 60 min before 4-fluoro-2-methoxypyridine (500 mg, 3.93 mmol) was added. The reaction mixture was stirred at 90 C for 4.5 h before quenching by the addition of water. The reaction mixture was extracted with EtOAc. The combined organic extracts were dried over MgS04 and concentrated in vacuo. The crude mixture was purified by flash chromatography (ISCO Combiflash, 0-30% EtOAc in hexanes) to afford 4-(3- iodo-lH-pyrazol-l-yl)-2-methoxypyridine, as a white solid. LCMS calc. = 301.97; found = 302.02 (M+H)+.
		INTERMEDIATE 24 4-(3-Iodo-l H-pyrazol- 1 -yl)-2-methoxypyridine To 3-iodo-lH-pyrazole (763 mg, 3.93 mmol) in DMSO (15 mL) at 0 C, was added sodium hydride (60% in mineral oil, 189 mg, 4.72 mmol). The reaction was warmed to 25 C and stirred for 60 min before 4-fluoro-2-methoxypyridine (500 mg, 3.93 mmol) was added. The reaction mixture was stirred at 90 C for 4.5 h before quenching by the addition of water. The reaction mixture was extracted with EtOAc. The combined organic extracts were dried over MgS04 and concentrated in vacuo. The crude mixture was purified by flash chromatography (ISCO Combiflash, 0-30% EtOAc in hexanes) to afford 4-(3-iodo-17J-pyrazol-l-yl)-2-methoxypyridine, as a white solid. LCMS calc. = 301.97; found = 302.02 (M+H)+.

Reference： [1]Patent: WO2014/99695,2014,A1 .Location in patent: Page/Page column 44; 45
[2]Patent: WO2014/99694,2014,A1 .Location in patent: Page/Page column 86
[3]Patent: WO2014/120346,2014,A1 .Location in patent: Page/Page column 44-45

10
[ 850246-04-7 ]
[ 4522-35-4 ]
[ 1616069-32-9 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of <strong>[4522-35-4]3-iodopyrazole</strong> (0.70 g, 3.61 mmol), in DMSO (18.0 mL) wasadded sodium hydride (60% disp. in oil, 0.173 g, 4.33 mmol), and the resultingmixture was stirred for 0.5 h before adding 4-fluoro-2-trifluoromethyl pyridine(0.596 g, 3.61 mmol). The reaction mixture was stirred at 90 oc for 3 h. Thereaction was quenched by the addition of water and extracted with EtOAc. Thecombined organic extracts were washed with water and brine, dried overMgS04 and concentrated in vacuo. The crude mixture was purified by flashchromatography (ISCO, 40 g, 0-50 % EtOAc in hexanes) to afford 4-(3-iodo-1H-pyrazol-1-yl)-2-(trifluoromethyl)pyridine, as a white solid. LCMS calc. =339.95; found= 339.93 (M+H)+. 1H NMR (500 MHz, CDCh): o 8.77 (d, J=5.3 Hz, 1 H); 8.03 (d, J = 3.8 Hz, 1 H); 7.91 (d, J = 2.6 Hz, 1 H); 7.77 (d, J =5.4 Hz, 1 H); 6.74 (d, J= 2.5 Hz, 1 H).
		To a solution of <strong>[4522-35-4]3-iodopyrazole</strong> (0.70 g, 3.61 mmol), in DMSO (18.0 mL) was added sodium hydride (60% disp. in oil, 0.173 g, 4.33 mmol), and the resulting mixture was stirred for 0.5 h before adding 4-fluoro-2-trifluoromethyl pyridine (0.596 g, 3.61 mmol). The reaction mixture was stirred at 90 C for 3 h. The reaction was quenched by the addition of water and extracted with EtOAc. The combined organic extracts were washed with water and brine, dried over MgS0 and concentrated in vacuo. The crude mixture was purified by flash chromatography (ISCO, 40 g, 0-50 % EtOAc in hexanes) to afford 4-(3-iodo- lH-pyrazol-l-yl)-2-(trifluoromethyl)pyridine, as a white solid. LCMS calc. = 339.95; found = 339.93 (M+H)+. 1H NMR (500 MHz, CDC13): delta 8.77 (d, J= 5.3 Hz, 1 H); 8.03 (d, J- 3.8 Hz, 1 H); 7.91 (d, J= 2.6 Hz, 1 H); 7.77 (d, J= 5.4 Hz, 1 H); 6.74 (d, J = 2.5 Hz, 1 H).
		INTERMEDIATE 20 4-(3-Iodo- lH-pyrazol-1 -yl)-2-(trifluoromethyl)pyridine To a solution of <strong>[4522-35-4]3-iodopyrazole</strong> (0.70 g, 3.61 mmol), in DMSO (18.0 mL) was added sodium hydride (60% disp. in oil, 0.173 g, 4.33 mmol), and the resulting mixture was stirred for 0.5 h before adding 4-fluoro-2-trifluoromethyl pyridine (0.596 g, 3.61 mmol). The reaction mixture was stirred at 90 C for 3 h. The reaction was quenched by the addition of water and extracted with EtOAc. The combined organic extracts were washed with water and brine, dried over MgS04 and concentrated in vacuo. The crude mixture was purified by flash chromatography (ISCO, 40 g, 0-50 % EtOAc in hexanes) to afford 4-(3-iodo-lH-pyrazol-l-yl)-2-(trifluoromethyl)pyridine, as a white solid. LCMS calc. = 339.95; found = 339.93 (Mu+Eta)+. NMR (500 MHz, CDC13): delta 8.77 (d, J= 5.3 Hz, 1 H); 8.03 (d, J= 3.8 Hz, 1 H); 7.91 (d, J= 2.6 Hz, 1 H); 7.77 (d, J= 5.4 Hz, 1 H); 6.74 (d, J= 2.5 Hz, 1 H).

Reference： [1]Patent: WO2014/99695,2014,A1 .Location in patent: Page/Page column 45
[2]Patent: WO2014/99694,2014,A1 .Location in patent: Page/Page column 86; 87
[3]Patent: WO2014/120346,2014,A1 .Location in patent: Page/Page column 42

11
4-iodopyridazine [ No CAS ]
[ 4522-35-4 ]
[ 1616069-42-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; In dimethyl sulfoxide; at 0 - 50℃;	To the stirred solution of 4-iodopyridazine (1 000 mg, 4.85 mmol) and 3-iodolH-pyrazole (951 mg, 4.90 mmol) in DMSO was added NaH ( 60% in oil, 233mg, 5.83 mmol) in portion at 0 C. The mixture was stirred at room temparature for 30 min or until bubbling ceased, then warmed up to 50 C and stirred at50 C overnight. The reaction mixture was cooled to room temperature,partitioned between EtOAc and water. The aqueous was extracted with EtOAcfor three times. The organic phases were combined, dried over Na2S04 andconcentrated in vacuo to give the crude product. This was purified by flashchromatography (Isco CombiFlash, 80 g Silica gel column, 0-100% EtOAc inhexanes) to afford 4-(3-iodo-1H-pyrazol-1-yl)pyridazine. LCMS calc.= 272.96;found= 272.96 (M+Ht. 1H NMR (500 MHz, CDCl)): o 9.64 (d, J = 3.0 Hz, 1H); 9.27 (d, J = 6.0 Hz, 1 H); 7.95 (d, J = 2.5 Hz, 1 H); 7.81 (dd, J = 2.5 Hz, J= 5.5 Hz, 1 H); 6.79 (d, J = 2.5 Hz, 1 H).
	With sodium hydride; In dimethyl sulfoxide; mineral oil; at 0 - 50℃;	To the stirred solution of 4-iodopyridazine (1000 mg, 4.85 mmol) and 3-iodo- lH-pyrazole (951 mg, 4.90 mmol) in DMSO was added NaH ( 60% in oil, 233 mg, 5.83 mmol) in portion at 0 C. The mixture was stirred at room temparature for 30 min or until bubbling ceased, then warmed up to 50 C and stirred at 50 C overnight. The reaction mixture was cooled to room temperature, partitioned between EtOAc and water. The aqueous was extracted with EtOAc for three times. The organic phases were combined, dried over Na S04 and concentrated in vacuo to give the crude product. This was purified by flash chromatography (Isco CombiFlash, 80 g Silica gel column, 0-100% EtOAc in hexanes) to afford 4-(3-iodo-lH-pyrazol-l -yl)pyridazine. LCMS calc. = 272.96; found = 272.96 (M+H)+. 1H NMR (500 MHz, CDC13): delta 9.64 (d, J = 3.0 Hz, 1 H); 9.27 (d, J = 6.0 Hz, 1 H); 7.95 (d, J = 2.5 Hz, 1 H); 7.81 (dd, J = 2.5 Hz, J = 5.5 Hz, 1 H); 6.79 (d, J = 2.5 Hz, 1 H).
	With sodium hydride; In dimethyl sulfoxide; mineral oil; at 0 - 50℃;	INTERMEDIATE 39 4-(3 -Iodo- 1 H-p yrazol- 1 -yl)pyridazine To the stirred solution of 4-iodopyridazine (1000 mg, 4.85 mmol) and 3-iodo-lH- pyrazole (951 mg, 4.90 mmol) in DMSO was added NaH ( 60% in oil, 233 mg, 5.83 mmol) in portion at 0 C. The mixture was stirred at room temparature for 30 min or until bubbling ceased, then wanned up to 50 C and stirred at 50 C overnight. The reaction mixture was cooled to room temperature, partitioned between EtOAc and water. The aqueous was extracted with EtOAc for three times. The organic phases were combined, dried over Na2S04 and concentrated in vacuo to give the crude product. This was purified by flash chromatography (Isco CombiFlash, 80 g Silica gel column, 0-100% EtOAc in hexanes) to afford 4-(3-iodo-lH-pyrazol-l- yl)pyridazine. LCMS calc. = 272.96; found = 272.96 (M+H)+. NMR (500 MHz, CDC13): delta 9.64 (d, J = 3.0 Hz, 1 H); 9.27 (d, J = 6.0 Hz, 1 H); 7.95 (d, J = 2.5 Hz, 1 H); 7.81 (dd, J = 2.5 Hz, J = 5.5 Hz, 1 H); 6.79 (d, J = 2.5 Hz, 1 H).

Reference： [1]Patent: WO2014/99695,2014,A1 .Location in patent: Page/Page column 45; 46
[2]Patent: WO2014/99694,2014,A1 .Location in patent: Page/Page column 87
[3]Patent: WO2014/120346,2014,A1 .Location in patent: Page/Page column 53-54

12
[ 4522-35-4 ]
[ 1837-55-4 ]
[ 1616070-35-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium tert-butylate; In N,N-dimethyl-formamide; at 100℃; for 1h;	To a soluton of<strong>[4522-35-4]3-iodopyrazole</strong> (500 mg, 2.58mmol) and 3,5-dichloropyridazine(384 mg, 2.58 mmol) in anhydrous DMF (5 mL) at room temperature was addedpotassium tert-butoxide (289 mg, 2.58 mmol) in one portion. It was heated at100 C for 1 h. It was cooled to room temperature, diluted with EtOAc (50 mL),washed with satd aq. NaHC03 (10 mL) and water (100 mL). The aqueous layerwas separated and extracted with EtOAc (3 x 50 mL). The combined organiclayers were washed with water (1 00 mL), brine (1 00 mL), dried over Na2S04,filtered and concentrated. The residue was purified by flash chromatography(ISCO Combiflash, Gold 40 g, 0-60% EtOAc in hexanes) to give 3-chloro-5-(3-iodo-1H-pyrazol-1-yl)pyridazine, as a white solid. LCMS calc.= 306.92, found= 306.96 (M+Ht. 1H NMR (500 MHz, CHCh-d): o 9.54 (d, J= 2.3 Hz, 1 H);7.94 (d, J= 2.7 Hz, 1 H); 7.90 (d, J= 2.3 Hz, 1 H); 6.81 (d, J= 2.7 Hz, 1 H).
	With potassium tert-butylate; In N,N-dimethyl-formamide; at 100℃; for 1h;	3-Chloro-5-(3-iodo-lH-pyrazol-l -vDpyridazine To a soluton of <strong>[4522-35-4]3-iodopyrazole</strong> (500 mg, 2.58 mmol) and 3,5-dichloropyridazine (384 mg, 2.58 mmol) in anhydrous DMF (5 mL) at room temperature was added potassium teri-butoxide (289 mg, 2.58 mmol) in one portion. It was heated at 100 C for 1 h. It was cooled to room temperature, diluted with EtOAc (50 mL), washed with satd aq. NaHC03 (10 mL) and water (100 mL). The aqueous layer was separated and extracted with EtOAc (3 x 50 mL). The combined organic layers were washed with water (100 mL), brine (100 mL), dried over Na2S04, filtered and concentrated. The residue was purified by flash chromatography (ISCO Combiflash, Gold 40 g, 0-60% EtOAc in hexanes) to give 3-chloro-5-(3- iodo-lH-pyrazol-l-yl)pyridazine, as a white solid. LCMS calc. = 306.92, found = 306.96 (M+H)+. NMR (500 MHz, CHCl3-d): delta 9.54 (d, J= 2.3 Hz, 1 H); 7.94 (d, J= 2.7 Hz, 1 H); 7.90 (d, J= 2.3 Hz, 1 H); 6.81 (d, J= 2.7 Hz, 1 H).
	With potassium tert-butylate; In N,N-dimethyl-formamide; at 100℃; for 1h;	INTERMEDIATE 40 3-Chloro-5-(3-iodo-lH-pyrazol-l-yl pyridazine To a soluton of <strong>[4522-35-4]3-iodopyrazole</strong> (500 mg, 2.58 mmol) and 3,5-dichloropyridazine (384 mg, 2.58 mmol) in anhydrous DMF (5 mL) at room temperature was added potassium tert-butoxide (289 mg, 2.58 mmol) in one portion. It was heated at 100 C for 1 h. It was cooled to room temperature, diluted with EtOAc (50 mL), washed with satd aq. NaHC03 (10 mL) and water (100 mL). The aqueous layer was seperated and extracted with EtOAc (3 x 50 mL). The combined organic layers were washed with water (100 mL), brine (100 mL), dried over Na2S04, filtered and concentrated. The residue was purified by flash chromatography (ISCO Combiflash, Gold 40 g, 0-60% EtOAc in hexanes) to give 3-chloro-5-(3-iodo-lH-pyrazol-l-yl)pyridazine, as a white solid. LCMS calc. = 306.92, found = 306.96 (M+H)+. NMR (500 MHz, CHC13- d): 5 9.54 (d, J= 2.3 Hz, 1 H); 7.94 (d, J= 2.7 Hz, 1 H); 7.90 (d, J= 2.3 Hz, 1 H); 6.81 (d, J= 2.7 Hz, 1 H).

Reference： [1]Patent: WO2014/99695,2014,A1 .Location in patent: Page/Page column 46
[2]Patent: WO2014/99694,2014,A1 .Location in patent: Page/Page column 87; 88
[3]Patent: WO2014/120346,2014,A1 .Location in patent: Page/Page column 54

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Technical Information

? Alkyl Halide Occurrence ? General Reactivity ? Hiyama Cross-Coupling Reaction ? Kinetics of Alkyl Halides ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Dihalides ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling

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[ 4522-35-4 ] Synthesis Path-Upstream 1~1

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