1H-Pyrazolo[3,4-b]pyridine, 4-chloro-1-[(4-Methoxyphenyl)Methyl]- synthesis
- Product Name:1H-Pyrazolo[3,4-b]pyridine, 4-chloro-1-[(4-Methoxyphenyl)Methyl]-
- CAS Number:924909-17-1
- Molecular formula:C14H12ClN3O
- Molecular Weight:273.72
![1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-ol](/CAS2/GIF/370866-00-5.gif)
370866-00-5
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Yield:924909-17-1 97%
Reaction Conditions:
with trichlorophosphate in dichloromethane;Reflux;Inert atmosphere;
Steps:
1
To a solution of l-(4-methoxybenzyl)-lH-pyrazolo [3,4-b]pyridin-4-ol (3) (7.9 g, 31 mmol) in anhydrous DCM (100 mL) was added POCI3 (30 g, 186 mmol). The resulting mixture was heated to reflux under N2 atmosphere overnight. After cooling to r.t., the reaction mixture was slowly poured into ice water (500 mL). Sat. NaHCC>3 solution was slowly added until the mixture became neutral. The resulting mixture was extracted with DCM (200 mL x 2). The combined organic phase was washed with brine, dried over Na2S04, filtered and concentrated to give the crude product which was purified by flash chromatography (silica gel, 0 to 10% ethyl acetate in petroleum ether) to afford 4-chloro- 1 -(4- methoxybenzyl)-lH-pyrazolo[3,4-Z?]pyridine (4) (8.2 g, 97% yield) as a red solid. LC-MS (ESI): mlz (M+l) 273.9.
References:
WO2016/4272,2016,A1 Location in patent:Paragraph 00561
![ethyl 4-hydroxy-1-(4-Methoxybenzyl)-1H-
pyrazolo[3,4-b]pyridine-5-carboxylate](/CAS/20150408/GIF/227617-15-4.gif)
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![1H-Pyrazolo[3,4-b]pyridine-5-carboxylic acid, 4-hydroxy-1-[(4-methoxyphenyl)methyl]-](/CAS/20210111/GIF/370865-99-9.gif)
370865-99-9
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924909-17-1
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227617-24-5
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3528-45-8
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