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

HRID 1615940Notes

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 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. and poured onto a solution of conc. aqueous ammonia (90 ml) and water (500 ml), ethyl acetate (200 ml) was added and the mixture was stirred briefly. The aqueous phase was removed and extracted twice more with ethyl acetate (200 ml each time). The combined organic phases were washed twice with 10% aqueous sodium chloride solution (100 ml each time), dried over sodium sulfate and concentrated under reduced pressure. The crude product was converted 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 removed
extractionextracted twice more with ethyl acetate (200 ml each time)
washThe combined organic phases were washed twice with 10% aqueous sodium chloride solution (100 ml each time)
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe crude product was converted without further purification

Sources & evidence

ORD record: ord-01e5d2672a6444d980227437c632136a
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765769B2

Reaction notes

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