ChemicalBook CAS DataBase List ethyl 4-chloro-1-(4-Methoxybenzyl)-1H- pyrazolo[3,4-b]pyridine-5-carboxylate

ethyl 4-chloro-1-(4-Methoxybenzyl)-1H- pyrazolo[3,4-b]pyridine-5-carboxylate synthesis

5synthesis methods

Product Name:ethyl 4-chloro-1-(4-Methoxybenzyl)-1H- pyrazolo[3,4-b]pyridine-5-carboxylate
CAS Number:227617-16-5
Molecular formula:C17H16ClN3O3
Molecular Weight:345.78

ethyl 4-hydroxy-1-(4-Methoxybenzyl)-1H-
pyrazolo[3,4-b]pyridine-5-carboxylate

227617-15-4
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ethyl 4-chloro-1-(4-Methoxybenzyl)-1H-
pyrazolo[3,4-b]pyridine-5-carboxylate

227617-16-5
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Yield:227617-16-5 95%

Reaction Conditions:

with trichlorophosphate in 1,2-dichloro-ethane at 90; for 3 h;

Steps:

34.3 Ethyl 4-chloro-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

To a solution of ethyl 1-(4-methoxybenzyl)-4-oxo-4,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (4.0 g, 13 mmol) in 1,2-dichloroethane (9.8 mL) was added POCl₃(2.4 mL, 26 mmol). The resulting mixture was heated at 90° C. for 3 h. After cooling, the most volatile were removed by vacuum, and the residue was diluted with EtOAc and washed with aq. Na₂CO₃solution. The organic layer was washed water and brine, dried and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using CombiFlash apparatus, eluting with 10 to 60% EtOAc in hexanes, to give the sub-title compound (3.9 g, 95%). LCMS calc. for C₁₇H₁₇ClN₃O₃(M+H)⁺: m/z=346.1. Found: 346.1.

References:

US2014/200227,2014,A1 Location in patent:Paragraph 0806; 0807

227617-15-4
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227617-16-5
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References