Trifluoroacetic acid → 2-(3-(1H-pyrazolo[3,4-b]pyridin-4-yl)phenyl)-2-methylbutanenitrile

HRID 384060Notes

Reaction equation

[CH3:1][C:2]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]3[N:19](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:20]=[CH:21][C:14]=23)[CH:8]=1)([CH2:5][CH3:6])[C:3]#[N:4].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[NH:19]1[C:15]2=[N:16][CH:17]=[CH:18][C:13]([C:9]3[CH:8]=[C:7]([C:2]([CH3:1])([CH2:5][CH3:6])[C:3]#[N:4])[CH:12]=[CH:11][CH:10]=3)=[C:14]2[CH:21]=[N:20]1

Participants

Conditions

Temperature: 0 °C

Procedure

2-Methyl-2-(3-(1-trityl-1H-pyrazolo[3,4-b]pyridin-4-yl)phenyl)butanenitrile (240 mg, 0.46 mmol) was dissolved in dichloromethane (10 ml) and cooled down in an ice-bath. Triethylsilane (2.5 ml) was added followed by trifluoroacetic acid (2.5 ml). The resulting mixture was stirred at 0° C. for 2 hours and then concentrated under reduced pressure. The residue was partitioned between ethyl acetate and a saturated aqueous solution of sodium carbonate. The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified on silica gel by flash column chromatography to afford the title compound as a white solid (92 mg, 70% yield).

Workup

temperaturecooled down in an ice-bath
concentrationconcentrated under reduced pressure
customThe residue was partitioned between ethyl acetate
dry with materialThe organic phase was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified on silica gel by flash column chromatography

Sources & evidence

ORD record: ord-e142016deaa94f85b170fec06d5ad514
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367697B2

Reaction notes

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