Ammonia → 5-Fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carbonitrile

HRID 1966411Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:10](I)=[N:9][N:8]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])[C:5]2=[N:6][CH:7]=1.[Cu](C#N)[C:21]#[N:22].N.O>CS(C)=O.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:10]([C:21]#[N:22])=[N:9][N:8]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])[C:5]2=[N:6][CH:7]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A suspension of 16.03 g (43.19 mmol) of 5-fluoro-1-(2-fluorobenzyl)-3-iodo-1H-pyrazolo[3,4-b]pyridine (Example 6A) and 4.25 g (47.51 mmol) of copper cyanide was initially charged in DMSO (120 ml) and stirred at 150° C. for 2 h. After cooling, the contents of the flask were cooled to about 40° C. and poured into a solution of conc. aqueous ammonia (90 ml) and water (500 ml), ethyl acetate (200 ml) was added and the mixture was subjected to brief extractive stirring. The aqueous phase was separated off and extracted two more times with ethyl acetate (200 ml each time). The combined organic phases were washed twice with 10% strength aqueous sodium chloride solution (100 ml each time), dried and concentrated under reduced pressure. The crude product was reacted without further purification.

Workup

temperatureAfter cooling
temperaturethe contents of the flask were cooled to about 40° C.
additionwas added
customThe aqueous phase was separated off
extractionextracted two more times with ethyl acetate (200 ml each time)
washThe combined organic phases were washed twice with 10% strength aqueous sodium chloride solution (100 ml each time)
customdried
concentrationconcentrated under reduced pressure
customThe crude product was reacted without further purification

Sources & evidence

ORD record: ord-bbe6da70332b4e72aeab4d977144ac56
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420656B2

Reaction notes

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