[ CAS No. 52333-42-3 ] {[proInfo.proName]}

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Quality Control of [ 52333-42-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 52333-42-3 ]

SDS Specification

Alternatived Products of [ 52333-42-3 ]

Product Details of [ 52333-42-3 ]

CAS No. :	52333-42-3	MDL No. :	MFCD01105748
Formula :	C₇H₄BrN₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YEDMUIQRKXNDQI-UHFFFAOYSA-N
M.W :	210.03	Pubchem ID :	4246943
Synonyms :

Safety of [ 52333-42-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 52333-42-3 ]

* 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 [ 52333-42-3 ]
Downstream synthetic route of [ 52333-42-3 ]

[ 52333-42-3 ] Synthesis Path-Upstream 1~1

1
[ 38875-53-5 ]
[ 131543-46-9 ]
[ 52333-42-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	for 48 h;	INTERMEDIATE 197-Bromopyrido[2,3-fr1pyrazine 2,3-Diamino-5-bromopyridine (2 g, 10.6 mmol) was dissolved in ethanol (25 mL) and glyoxal (5 mL, 40percent in water) was added. After standing for 48 h the mixture was concentrated in vacuo and the residue triturated with diethyl ether to give, after air-drying, the title compound (2.04 g, 92percent) as a pink-brown solid. δ_H (d₆ DMSO) 9.28 (d, IH), 9.20 (d, IH), 9.12 (d, IH), 8.95 (d, IH). LCMS (ES+) 212 (M+H)⁺, RT 1.98 minutes.

Reference： [1] Patent: WO2010/52448, 2010, A2, . Location in patent: Page/Page column 41-42

[ 52333-42-3 ] Synthesis Path-Downstream 1~12

1
[ 52333-42-3 ]
[ 4542-61-4 ]
[ 144-55-8 ]
[ 32005-36-0 ]
[ 397325-35-8 ]

Yield	Reaction Conditions	Operation in experiment
60%	With caesium carbonate; triphenylphosphine; In 1,4-dioxane;	Example 105 Under nitrogen atmosphere, to a mixture of <strong>[52333-42-3]7-bromopyrido[2,3-b]pyrazine</strong> (300 mg), methyl boronate (100 mg) and cesium carbonate (930 mg) were added dioxane (7.0 ml), bis(dibenzilidenacetone)-palladium (80.0 mg) and triphenylphosphine (87.0 mg), and the mixture was stirred at 100 C. for 2.5 hours. To the reaction solution was added a saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted three times with ethyl acetate. The extracts were combined, washed with a saturated brine, dried over magnesium sulfate, and filtered. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column (hexane/ethyl acetate=3/1?1/1?0/1?ethyl acetate/ethanol=10/1) to give 7-methyl-pyrido[2,3-b]pyrazine (125 mg, 60%). 1H NMR (CDCl3, 400 MHz) delta 9.06 (d, 1H, J=2.3 Hz), 9.02 (d, 1H, J=1.7 Hz), 8.91 (d, 1H, J=1.7 Hz), 8.24 (d, 1H, J=2.3 Hz), 2.65 (s, 3H).

Reference： [1]Patent: US2003/181496,2003,A1

2
potassium phosphate [ No CAS ]
[ 52333-42-3 ]
palladium(1,1'-bis(diphenylphosphino)ferrocenyl) dichloride [ No CAS ]
[ 3054-95-3 ]
7-(3,3-diethoxypropyl)-pyrido[2,3-b]pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran;	Step AAA: 7-(3,3-diethoxypropyl)-pyrido[2,3-b]pyrazine To a solution of 9-BBN (10.2 mL of a 0.5M solution in tetrahydrofuran) at 0 C. was added dropwise 0.77 mL of acrolein diethyl acetal and the mixture allowed to warm slowly to room temperature. After 15 hours, the mixture was diluted with 12 mL dry tetrahydrofuran followed by the sequential addition of potassium phosphate (1.6 g), palladium(1,1'-bis(diphenylphosphino)ferrocenyl) dichloride (160 mg) and <strong>[52333-42-3]7-bromo-pyrido[2,3-b]pyrazine</strong> (924 mg) and then heated to reflux on an oil bath. After 5 hours, the mixture was cooled to 0 C., diluted with 15 mL benzene and the excess reagents quenched by the addition of 2N sodium hydroxide (3.5 mL) and 30% hydrogen peroxide (2.5 mL). The mixture then extracted with ethyl acetate, washed with brine and the concentrate purified by flash chromatography on silica gel (ethyl acetate:hexane, 1:4; then 1:1; then 4:1) to give the title compound (1.2 g).

Reference： [1]Patent: US6159975,2000,A

3
[ 52333-42-3 ]
bis(dibenzilidenacetone)palladium [ No CAS ]
[ 4542-61-4 ]
[ 144-55-8 ]
[ 397325-35-8 ]

Yield	Reaction Conditions	Operation in experiment
60%	With caesium carbonate; triphenylphosphine; In 1,4-dioxane;	(105-1) Under nitrogen atmosphere, to a mixture of <strong>[52333-42-3]7-bromopyrido[2,3-b]pyrazine</strong> (300 mg), methyl boronate (100 mg) and cesium carbonate (930 mg) were added dioxane (7.0 ml), bis(dibenzilidenacetone)palladium (80.0 mg) and triphenylphosphine (87.0 mg), and the mixture was stirred at 100C for 2.5 hours. To the reaction solution was added a saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted three times with ethyl acetate. The extracts were combined, washed with a saturated brine, dried over magnesium sulfate, and filtered. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column (hexane/ethyl acetate = 3/1 ? 1/1 ? 0/1 ? ethyl acetate/ethanol = 10/ 1) to give 7-methylpyrido[2,3-b]pyrazine (125 mg, 60 %). 1H NMR (CDCl3, 400MHz) delta 9.06 (d, 1H, J=2.3Hz), 9.02 (d, 1H, J=1.7Hz), 8.91 (d, 1H, J=1.7Hz), 8.24 (d, 1H, J=2.3Hz), 2.65 (s, 3H).

Reference： [1]Patent: EP1479384,2004,A1

4
[ 52333-42-3 ]
[ 73183-34-3 ]
[ 1210047-44-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium acetate;tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; In 1,4-dioxane; at 80.0℃;Inert atmosphere;	Under an argon atmosphere, 52 mg (0.057 mmol) of tris-(dibenzylidene-acetone)-dipalladium(0) and 38 mg (0.137 mmol) of tricyclohexylphosphine were dissolved in 5.8 ml dioxane. \|66 mg (1.047 mmol) of 4,4,4'415,5,5'5l-octamethyl-2,21-bi-l,3,2-dioxaborolan, 200 mg (0.952 mmol) of 7- bromopyrido[2,3-b]pyrazine (described in WO 2006/009734, p. 59) and 140 mg (1.428 mmol) potassium acetate were added and the mixture was stirred overnight at 800C. After cooling, the reaction mixture was concentrated in a rotary evaporator at reduced pressure, the residue was taken up in cyclohexane/ethyl acetate (v/v = 1 :1) and filtered on silica gel. The cyclohexane/ethyl acetate phase was discarded and the silica gel was rinsed with dichloromethane/methanol (v/v = 10:1). The filtrate was concentrated in a rotary evaporator at reduced pressure. We obtained 178 mg (38% of theor.) of the raw product, at a purity of 52% according to GC-MS. The raw product was reacted further without further purification.GC-MS (method 8): R, = 7.29 min; MS (EIpos): m/z = 257 [M]+.

Reference： [1]Patent: WO2010/20363,2010,A1 .Location in patent: Page/Page column 67-68

5
[ 38875-53-5 ]
[ 131543-46-9 ]
[ 52333-42-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	In ethanol; water; for 48.0h;	INTERMEDIATE 197-Bromopyrido[2,3-fr1pyrazine 2,3-Diamino-5-bromopyridine (2 g, 10.6 mmol) was dissolved in ethanol (25 mL) and glyoxal (5 mL, 40% in water) was added. After standing for 48 h the mixture was concentrated in vacuo and the residue triturated with diethyl ether to give, after air-drying, the title compound (2.04 g, 92%) as a pink-brown solid. deltaH (d6 DMSO) 9.28 (d, IH), 9.20 (d, IH), 9.12 (d, IH), 8.95 (d, IH). LCMS (ES+) 212 (M+H)+, RT 1.98 minutes.

Reference： [1]Patent: WO2010/52448,2010,A2 .Location in patent: Page/Page column 41-42

6
[ 52333-42-3 ]
[ 1021186-08-2 ]
[ 1225279-44-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 120.0℃; for 0.333333h;Sealed tube; Microwave irradiation;	EXAMPLE 427-[3-(Piperidin-l-ylmethyl)phenyllpyridor2,3-Z)lpyrazine, bis(acetic acid) saltIntermediate 19 (41 mg, 0.21 mmol), 3-(piperidin-l-ylmethyl)phenylboronic acid pinacol ester hydrochloride (70 mg, 0.21 mmol), 2M aqueous sodium carbonate solution (0.3 mL, 0.6 mmol) and Pd(PPh3)4 (7 mg, 0.006 mmol) in DME (0.6 mL) were heated to 1200C in a sealed tube, under microwave irradiation, for 20 minutes. After cooling, the organic phase was concentrated in vacuo and the residue was purified by preparative HPLC to give the title compound (68 mg, 76%) as a beige solid. deltaH (CDCl3) 9.49 (d, IH), 9.08 (d, IH), 8.99 (d, IH), 8.65 (d, IH), 7.82 (s, IH), 7.73 (d, IH), 7.55 (t, IH), 7.49 (d, IH), 3.84 (s, 2H), 2.59-2.75 (m, 4H), 2.09 (s, 6H), 1.65-1.79 (m, 4H), 1.43-1.60 (m, 2H). LCMS (ES+) 305 (M+H)+, RT 2.02 minutes.

Reference： [1]Patent: WO2010/52448,2010,A2 .Location in patent: Page/Page column 73

7
[ 52333-42-3 ]
[ 20474-15-1 ]
C₃₂H₂₂N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With palladium diacetate; sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate; In toluene; at 110.0℃; for 48.0h;	(2) A mixture of intermediate 2 (1.0 g, 4.76 mmol), 9,9-diphenylacridine (1.75 g, 5.24 mmol), sodium tert-butoxide (0.63 g, 6.56 mmol), palladium acetate (0.025 g, 0.11 mmol), tri-tert-butylphosphine tetrafluoroborate (0.095 g, 0.33 mmol), and toluene 45 mL were charged together into a 100 mL round bottom flask. Refluxed at 110C for 48 hours. The reaction was then quenched with 10 mL of saturated aqueous sodium chloride. After extraction with dichloromethane, dried over anhydrous sodium sulfate. Finally, silica gel column chromatography was carried out using dichloromethane / petroleum ether (v / v = 3: 2) as the eluent to obtain compound 4. Yield: 94%.

Reference： [1]Patent: CN106008501,2016,A .Location in patent: Paragraph 0059; 0060; 0061

8
[ 52333-42-3 ]
(1,3-bis(2,6-diisopropylphenyl)imidazolidin-2-yl)(difluoromethyl)silver [ No CAS ]
C₈H₅F₂N₃ [ No CAS ]

Reference： [1]Chemical Science,2017,vol. 8,p. 4848 - 4852

9
[ 52333-42-3 ]
potassium trifluoro(3,3,3-trifluoroprop-1-en-2-yl)borate [ No CAS ]
C₁₀H₆F₃N₃ [ No CAS ]

Reference： [1]Chemical Science,2018,vol. 9,p. 3215 - 3220

10
[ 52333-42-3 ]
[ 1227040-87-0 ]
C₃₃H₂₃N₃ [ No CAS ]

Reference： [1]RSC Advances,2019,vol. 9,p. 11865 - 11869

11
[ 52333-42-3 ]
[ 4248-19-5 ]
tert-butyl pyrido[2,3-b]pyrazin-7-ylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 110.0℃; for 16.0h;Inert atmosphere;	A mixture of <strong>[52333-42-3]7-bromopyrido[2,3-b]pyrazine</strong> (500 mg, 2.38 mmol), BocNH2 (335 mg, 2.86 mmol), Pch(dba)3 (109 mg, 0.119 mmol), XantPhos (207 mg, 0.357 mmol) and CS2CO3 (1.16 g, 3.57 mmol) in anhydrous dioxane (10 mL) was degassed and purged with N2 for 3 times. Then the resulting reaction mixture was heated at 110 C for 16 h. A black suspension was formed. To the reaction mixture was added water (25 mL) and EtOAc (25 mL), then filtered through a pad of celite and the solid was washed with EtOAc (20 mL x3). The filtrate was separated and the aqueous layer was extracted with EtOAc (25 mL x2). The combined organic layer was washed with brine (25 mL), dried over anhydrous NaiSOr and concentrated. The residue was purified by Combi Flash (35% to 70% EtOAc in pentane) to give tert-butyl pyrido[2,3-b]pyrazin-7-ylcarbamate (150 mg, yield: 26%) as a yellow solid. (0977) NMR (400 MHz, DMSO-r e) d 1.54 (9H, s), 8.61 (1H, s), 8.95-9.00 (2H, m), 9.13 (1H, d, .7= 2.8 Hz), 10.29 (1H, brs).

Reference： [1]Patent: WO2019/126730,2019,A1 .Location in patent: Paragraph 0375

12
[ 52333-42-3 ]
pyrido[2,3-b]pyrazin-7-amine hydrochloride [ No CAS ]

Reference： [1]Patent: WO2019/126730,2019,A1

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Technical Information

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H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 52333-42-3 ] {[proInfo.proName]}

Quality Control of [ 52333-42-3 ]

Related Doc. of [ 52333-42-3 ]

Product Details of [ 52333-42-3 ]

Safety of [ 52333-42-3 ]

Application In Synthesis of [ 52333-42-3 ]

[ 52333-42-3 ] Synthesis Path-Upstream 1~1

[ 52333-42-3 ] Synthesis Path-Downstream 1~12

Technical Information

Related Functional Groups of [ 52333-42-3 ]

Bromides

Related Parent Nucleus of [ 52333-42-3 ]

Other Aromatic Heterocycles

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[ 52333-42-3 ]

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[ 52333-42-3 ]