[ CAS No. 885276-93-7 ] {[proInfo.proName]}

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Quality Control of [ 885276-93-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 885276-93-7 ]

SDS Specification

Alternatived Products of [ 885276-93-7 ]

Product Details of [ 885276-93-7 ]

CAS No. :	885276-93-7	MDL No. :	MFCD06739182
Formula :	C₁₀H₉BrN₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LJKZKCQPVABNLG-UHFFFAOYSA-N
M.W :	269.10	Pubchem ID :	53249841
Synonyms :

Calculated chemistry of [ 885276-93-7 ] Expand+

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.2
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	58.98
TPSA :	43.6 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.54 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.31
Log Po/w (XLOGP3) :	1.97
Log Po/w (WLOGP) :	2.27
Log Po/w (MLOGP) :	2.31
Log Po/w (SILICOS-IT) :	1.76
Consensus Log Po/w :	2.13

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.0
Solubility :	0.272 mg/ml ; 0.00101 mol/l
Class :	Soluble
Log S (Ali) :	-2.51
Solubility :	0.83 mg/ml ; 0.00308 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.42
Solubility :	0.102 mg/ml ; 0.00038 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	1.9

Safety of [ 885276-93-7 ]

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 [ 885276-93-7 ]

* 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 [ 885276-93-7 ]
Downstream synthetic route of [ 885276-93-7 ]

[ 885276-93-7 ] Synthesis Path-Upstream 1~1

1
[ 13061-96-6 ]
[ 885276-93-7 ]
[ 51135-70-7 ]

Yield	Reaction Conditions	Operation in experiment
77%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In N,N-dimethyl-formamide at 100℃; for 2 h;	A solution of ethyl 5-bromopyrazolo[1,5-ajpyridine-3-carboxylate (1.0 g, 3.73 mmol),methylboronic acid (448 mg, 7.46 mmol), Pd(dppf)C12 (545 mg, 0.746 mmol) and C52CO3(2.42 g, 7.46 mmol) was dissolved in DMF (5.0 mL), then the mixture was stirred at 100 °Cfor two hours. It was concentrated, and purified by silica gel chromatography with PE:EA=5: 1to obtain the desired compound as an orange solid (589 mg, 77percent). ESI MS m/z = 204.5[M+Hj.

Reference： [1] Patent: WO2017/15449, 2017, A1, . Location in patent: Page/Page column 342

[ 885276-93-7 ] Synthesis Path-Downstream 1~1

1
[ 885276-93-7 ]
[ 1060812-84-1 ]

Yield	Reaction Conditions	Operation in experiment
99.5%	With sulfuric acid; at 100℃; for 4.0h;	A solution of ethyl 5-bromopyrazolo[1,5-a]pyridine-3-carboxylate (240 mg, 0.89 mmol) in 40percent H2SO4 (12 mL) was stirred at 100° C. for 4 hours, then cooled to rt, and neutralized to pH=7 with aq. NaOH (6 M) in ice bath. The resulted mixture was extracted with DCM (25 mL×2). The combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo to give the title compound as a light yellow solid (175 mg, 99.5percent). MS (ESI, pos. ion) m/z: 196.9 [M+H]+.
96%		General procedure: These were made by decarboxylation/Vilsmeier or hydrolysis/reduction/reoxidation as detailed below, unless otherwise stated.Decarboxylation was carried out by refluxing a solution of the ester (1 equiv) in 40percent aqueous H2SO4 (3 mL) for 18 h. The solution was then cooled in ice and neutralised to pH 7 with 6 M NaOH, then extracted twice with CH2Cl2. The combined extracts were dried (Na2SO4) and the solvent removed in vacuo to leave the decarboxylated material. The pyrazolo[1,5-a]pyridine was then reacted under Vilsmeier conditions in dry DMF (2 mL) with POCl3 (3 equiv) at 0 °C under an atmosphere of N2. The reaction mixture was then warmed to room temperature and stirred for 2 h. The solution was poured onto ice, basified to pH 10 with 1 M NaOH, stirred for 1 h then extracted twice with CH2Cl2. The combined extracts were washed twice with water, dried (Na2SO4) and the solvent removed in vacuo to leave the aldehyde.Alternatively, the ester was hydrolysed by refluxing a solution of the ester (1 equiv) in 1 M NaOH (3 equiv) and EtOH (5 mL) for 6 h. The EtOH was removed in vacuo, and then the aqueous residue acidified to pH 1 with 1 M HCl. The precipitated carboxylic acid was filtered off, washed with water and dried. The carboxylic acid was reduced by adding CDI (1.5 equiv) to a suspension of carboxylic acid (1 equiv) in dry THF (10 mL) under an atmosphere of N2. After stirring for 18 h, the resulting solution was added dropwise to a solution of NaBH4 (5 equiv) in H2O (10 mL) and stirred for 30 min. The reaction was then quenched by the addition of 1 M HCl and stirred for a further 30 min. The solution was neutralised with saturated aqueous NaHCO3 and extracted twice with CH2Cl2. The combined organic layers were dried (Na2SO4) and the solvent removed in vacuo. Chromatography (eluting with a hexanes: EtOAc gradient) gave the alcohol. Reoxidation was carried out by stirring a suspension of the pyrazolo[1,5-a]pyridine-3-methanol (1 equiv) and MnO2 (10 equiv) in CH2Cl2 (2 mL) at room temperature for 4 days. The reaction mixture was then filtered through celite, washed with CH2Cl2, and the solvent removed from the filtrate in vacuo to leave the aldehyde.
60%	With sulfuric acid; In water; at 110℃; for 16.0h;	A suspension of ethyl 5-bromopyrazolo[1 ,5-a]pyridine-3-carboxylate 94-1 (1 .6 g, 5.94 mmol) in 70percent aq. H2S04 (15 mL) was maintained at 110 00 for 16 h. The reaction mixture was cooled to room temperature and poured into ice-cold water. The pH was adjusted to 7.0 using aq. 1 N NaOH solution, filtered the precipitated solid, washed with water, pet- ether and dried under vacuum to afford 700 mg (60percent) of 5-bromopyrazolo[1,5-a]pyridine 94-2 as an off white solid. ESI-LC/MS: m/z 196.74 (M+H) & 198.71 & [(M+2)+H]; R = 2.39 mm [Waters Acquity UPLC with Quattro-micro detector; Waters Acquity BEH 018, 1 .7 pm, 2.1 X 50mm column; gradient of 90:10 H20 (0.025percent TEA): CH3CN (0.025percent TEA) hold for 0.5 mm and to 10:90 H20 (0.025percent TEA) :CH3CN (0.025percent TEA) in 3.5 mm and hold for 1.5 mm with flow rate of 0.4 mL/min].

55%	With sulfuric acid; at 80℃;	Compound 64.4. 5-BromopyrazoIo[l,5-a] pyridine. Into a 50-mL round-bottom flask, was placed ethyl 5-bromopyrazolo[l ,5-a]pyridine-3-carboxylate (compound 64.3, 100 mg, 0.37 mmol). Sulfuric acid (50percent, 4 mL) was added carefully in portions at room temperature, then the resulting solution was stirred overnight at 80 °C. After cooling to room temperature, the pH of the solution was carefully adjusted to 8-9 with aqueous sodium hydroxide (5 M) and then extracted with ethyl acetate (2 x 20 mL). The combined organic extracts were washed with brine (20 mL), dried (Na2S04), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1 : 10) as the eluent to yield the title compound as a brown solid (40 mg, 55
55%	With sulfuric acid; at 80℃;	Compound 64.4. 5-Bromopyrazolo[l,5-]pyridine. Into a 50-mL round-bottom flask, was placed ethyl 5-bromopyrazolo[l,5-a]pyridine-3-carboxylate (compound 64.3, 100 mg, 0.37 mmol). Sulfuric acid (50percent, 4 mL) was added carefully in portions at room temperature, then the resulting solution was stirred overnight at 80 °C. After cooling to room temperature, the pH of the solution was carefully adjusted to 8-9 with aqueous sodium hydroxide (5 M) and then extracted with ethyl acetate (2 x 20 mL). The combined organic extracts were washed with brine (20 mL), dried (Na2S04), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1 : 10) as the eluent to yield the title compound as a brown solid (40 mg, 55 percent)
550 mg	With sulfuric acid; at 120℃; for 3.0h;	A colorless mixture of A-13 (900.0 mg, 3.34 mmol) in H2504 (50percent,10.0 mL) was stirred at 120 °C for 3 hours. The mixture was diluted with ice-water, neutralizedwith solid Na2CO3 to pH = 7, and extracted with DCM (50 mL x 2). The combined organiclayers were washed with brine (10 mL), dried over Na2504, filtered and concentrated to affordA-14 (550.00 mg, 2.79 mmol) as an oil. ?H NMR (400 MHz, CDC13) oe11 8.38 - 8.32 (m, 1H),7.95 (d, 1H), 7.72 (d, 1H), 6.83 (dd, 1H), 6.47 (d, 1H).

Reference： [1]Patent: US2014/234254,2014,A1 .Location in patent: Paragraph 0329; 0330; 0341; 0342
[2]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 69 - 85
[3]Patent: WO2014/78802,2014,A1 .Location in patent: Page/Page column 158
[4]Patent: WO2014/8197,2014,A1 .Location in patent: Page/Page column 136
[5]Patent: WO2015/95767,2015,A1 .Location in patent: Page/Page column 151
[6]Patent: WO2018/98500,2018,A1 .Location in patent: Page/Page column 88; 89

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Technical Information

? Acyl Group Substitution ? Alkyl Halide Occurrence ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bouveault-Blanc Reduction ? Catalytic Hydrogenation ? Complex Metal Hydride Reductions ? Ester Cleavage ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Preparation of Alkylbenzene ? Preparation of Amines ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Reactions with Organometallic Reagents ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Vilsmeier-Haack Reaction

Historical Records

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[ 885276-93-7 ]

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[ CAS No. 885276-93-7 ] {[proInfo.proName]}

Quality Control of [ 885276-93-7 ]

Related Doc. of [ 885276-93-7 ]

Product Details of [ 885276-93-7 ]

Calculated chemistry of [ 885276-93-7 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 885276-93-7 ]

Application In Synthesis of [ 885276-93-7 ]

[ 885276-93-7 ] Synthesis Path-Upstream 1~1

[ 885276-93-7 ] Synthesis Path-Downstream 1~1

Technical Information

Related Functional Groups of [ 885276-93-7 ]

Bromides

Esters

Related Parent Nucleus of [ 885276-93-7 ]

Other Aromatic Heterocycles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 885276-93-7 ]

Related Parent Nucleus of
[ 885276-93-7 ]