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1H-Pyrazolo[3,4-b]pyridine,3-methyl-(9CI)

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1H-Pyrazolo[3,4-b]pyridine,3-methyl-(9CI) Basic information
Product Name:1H-Pyrazolo[3,4-b]pyridine,3-methyl-(9CI)
Synonyms:1H-Pyrazolo[3,4-b]pyridine,3-methyl-(9CI);3-methyl-1H-pyrazolo[3,4-b]pyridine;3-Methyl-1H-pyrazolo[3,4-b]pyridine ,97%;3-methyl-1H-pyrazolo[3,4-b]pyridine (en);1H-Pyrazolo[3,4-b]pyridine,3-Methyl-;3-METHYL-2H-PYRAZOLO[3,4-B]PYRIDINE;1H-Pyrazolo[3,4-b]pyridine,3-methyl-(9CI) ISO 9001：2015 REACH
CAS:116834-96-9
MF:C7H7N3
MW:133.15
EINECS:
Product Categories:Heterocycle-Pyridine series;PYRIDINE
Mol File:116834-96-9.mol
1H-Pyrazolo[3,4-b]pyridine,3-methyl-(9CI) Structure
1H-Pyrazolo[3,4-b]pyridine,3-methyl-(9CI) Chemical Properties
Melting point 158-160°
Boiling point 255.7±23.0 °C(Predicted)
density 1.31±0.1 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
pka6.52±0.20(Predicted)
AppearanceLight yellow to yellow Solid
CAS DataBase Reference116834-96-9
Safety Information
Risk Statements 20/21/22
Safety Statements 36/37
HazardClass IRRITANT
HS Code 29331990
MSDS Information
1H-Pyrazolo[3,4-b]pyridine,3-methyl-(9CI) Usage And Synthesis
Chemical PropertiesWhite solid
Synthesis
3-ACETYL-2-CHLOROPYRIDINE

55676-21-6

1H-Pyrazolo[3,4-b]pyridine,3-methyl-(9CI)

116834-96-9

Step 3: Synthesis of 3-methyl-1H-pyrazolo[3,4-b]pyridine 1-(2-chloropyridin-3-yl)ethanone (22 g, 0.1415 mol) was dissolved with 98% hydrazine hydrate (113 g, 2.21 mol) in ethanol (300 mL) and reacted at reflux for 12 hours. Upon completion of the reaction, about 80% of the ethanol was removed by distillation under reduced pressure using a rotary evaporator. The residue was cooled to room temperature and the precipitated solid was collected by filtration and washed with cold water. The resulting product was dried to constant weight at 90 °C to give 3-methyl-1H-pyrazolo[3,4-b]pyridine (16 g, 85% yield) with a melting point of 152-154 °C. 1H NMR (CDCl3) δ: 8.62 (dd, J = 4.5, 1.4 Hz, 1H), 8.08 (dd, J = 8.0, 1.4 Hz, 1H), 7.15 (dd, J = 8.0, 4.5 Hz, 1H), 2.64 (s, 3H). MS (FAB) m/z: 133 (M++1).

References[1] European Journal of Medicinal Chemistry, 2012, vol. 57, p. 311 - 322
[2] Patent: US2006/47126, 2006, A1. Location in patent: Page/Page column 30
[3] Patent: WO2011/5759, 2011, A2. Location in patent: Page/Page column 77-78
[4] Canadian Journal of Chemistry, 1988, vol. 66, # 3, p. 420-428
[5] Patent: WO2011/84486, 2011, A1. Location in patent: Page/Page column 106; 111
1H-Pyrazolo[3,4-b]pyridine,3-methyl-(9CI) Preparation Products And Raw materials
Raw materialsEthanol-->Zinc chloride-->polyphosphoric acid-->3-Amino-5-methylpyrazole-->1,1,3,3-Tetramethoxypropane-->2-Fluoropyridine-->3-Acetyl-2-chloropyridine-->N-Methoxy-N-methylacetamide-->HYDRAZINE
Tag:1H-Pyrazolo[3,4-b]pyridine,3-methyl-(9CI)(116834-96-9) Related Product Information
4-Chloro-1,3-dimethylpyrazolo[3,4-b]pyridine-5-carboxylic acid 4-Chloro-1,3-dimethylpyrazolo[3,4-b]pyridine-5-carbonyl chloride 1H-Pyrazolo[3,4-b]pyridine Ethyl 4-chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate Ethyl 4-(3,5-dichlorophenoxy)-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate 6-Hydrazino-1,3,4-trimethyl-1H-pyrazolo[3,4-b]pyridine 1,3-Dimethyl-1H-pyrazolo[3,4-b]pyridin-4-ol Ethyl 1,3-dimethyl-4-(4-fluorophenoxy)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate Ethyl 4-(4-methoxyphenoxy)-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate 6-Chloro-1,4-dimethyl-3-(2-thienyl)-1H-pyrazolo[3,4-b]pyridine N-[(4-Chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridin-5-yl)carbonyl]-N'-(4-fluorophenyl)urea O1-[(4-Chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridin-5-yl)carbonyl]-4-(trifluoromethyl)benzene-1-carbohydroximamide 4-Chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxamide O1-[(4-Chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridin-5-yl)carbonyl]-4-chlorobenzene-1-carbohydroximamide N5-(1-Methyl-1-oxo-1-phenyl-lambda6-sulphanylidene)-6-chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxamide N-[(4-Chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridin-5-yl)carbonyl]-N'-[3,5-di(trifluoromethyl)phenyl]urea N5-(2-Chlorophenyl)-4-chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxamide O-[1,4-Dimethyl-3-(2-thienyl)-1H-pyrazolo[3,4-b]pyridin-6-yl] O,O-diethyl phosphothioate