Dichloromethane → (5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)(2,6-dichloro-3-fluorophenyl)acetonitrile

Participants

Reaction Steps

To a stirred mixture of trimethylsilyl cyanide (0.51 mL, 3.8 mmol) and indium(III) bromide (34.1 mg, 0.0961 mmol) in DCM (5.00 mL, 78.0 mmol) was added (5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-(2,6-dichloro-3-fluorophenyl)methanol (150.0 mg, 0.3846 mmol). The resulting mixture was stirred at rt overnight. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography (DCM/Hexane 1:1 as eluent). 1H NMR (400 MHz, CD3OD): δ=6.52 (s, 1H), 7.39 (d, J=1.0 Hz, 1H), 7.45 (t, J=8.7 Hz, 1H), 7.63 (dd, J=9.1, 4.8 Hz, 1H), 8.02 (d, J=2.0 Hz, 1H), 8.31 (d, J=2.3 Hz, 1H). MS (ES+): m/z 397.85, 399.88, 401.85 [MH+]. HPLC: tR=4.19 min (OpenLynx, polar—5 min).

Provenance & Evidence