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

HRID 1505452Notes

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].O.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 7A) 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., poured into a solution of conc. ammonia water (90 ml) and water (500 ml), ethyl acetate (200 ml) was added and the mixture was stirred briefly. The aqueous phase was separated off and extracted two more times with ethyl acetate (200 ml each). The combined organic phases were washed twice with 10% strength aqueous sodium chloride solution (100 ml each), 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
stirringthe mixture was stirred briefly
customThe aqueous phase was separated off
extractionextracted two more times with ethyl acetate (200 ml each)
washThe combined organic phases were washed twice with 10% strength aqueous sodium chloride solution (100 ml each)
customdried
concentrationconcentrated under reduced pressure
customThe crude product was reacted without further purification

Sources & evidence

ORD record: ord-1e0d93b3919e43a59a8a13aba547131c
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216978B2

Reaction notes

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