Acetonitrile → 1-(3,3,3-trifluoropropyl)-1H-pyrazolo[3,4-b]pyridine-3-carbonitrile

HRID 2203372Notes

Reaction equation

[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]#[N:11])=[N:2]1.Br[CH2:13][CH2:14][C:15]([F:18])([F:17])[F:16].C(=O)([O-])[O-].[K+].[K+].C(#N)C>O.CCOC(C)=O>[F:16][C:15]([F:18])([F:17])[CH2:14][CH2:13][N:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]#[N:11])=[N:2]1

Participants

Conditions

Temperature: 40 °C

Procedure

1H-pyrazolo[3,4-b]pyridine-3-carbonitrile, as described in Step C of Example 158 (30 g, 208 mmol), 3-bromo-1,1,1-trifluoropropane (44.5 mL, 416 mmol) and potassium carbonate (95 g, 687 mmol) were combined in a flask with acetonitrile (300 mL) and stirred at 40° C. After 5 h, the reaction was cooled to rt and EtOAc and water were added. The layers were separated and the aqueous layer was washed two times with EtOAc. The combined organics were dried (Na2SO4) and filtered. The solvent was removed under reduced pressure and the material was used without further purification. 1H NMR (500 MHz, DMSO-d6): δ 8.77 (d, J=4.50 Hz, 1H); 8.46 (d, J=8.23 Hz, 1H); 7.51 (dd, J=8.22, 4.47 Hz, 1H); 4.86 (t, J=6.66 Hz, 2H); 3.10-2.98 (m, 2H). m/z=241.1 (M+H).

Workup

temperaturethe reaction was cooled to rt
customThe layers were separated
washthe aqueous layer was washed two times with EtOAc
dry with materialThe combined organics were dried (Na2SO4)
filtrationfiltered
customThe solvent was removed under reduced pressure
customthe material was used without further purification

Sources & evidence

ORD record: ord-8b44b416171b4d22bfcd5e3a2199f24e
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365574B2

Reaction notes

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