Ethanol → HCID 178422173, compound

Participants

Reaction Steps

A mixture of 3-[4-(3-{(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl]ethyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)-5-methyl-1H-pyrazol-1-yl]cyclobutanone (10.0 mg, 0.0204 mmol), sodium borohydride (3.87 mg, 0.102 mmol) and EtOH (1 mL, 20 mmol) was stirred at rt for 30 min. Sat. NH4Cl was added, and the organic solvent was removed in vacuo. The material was extracted with DCM and water. The organic layer was concentrated in vacuo, redissolved in MeOH (0.7 mL) and purified via HPLC. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a white solid. 1H NMR (400 MHz, CD3OD): δ=1.84 (d, J=7.1 Hz, 3H), 2.17 (s, 3H), 2.48-2.58 (m, 2H), 2.78-2.87 (m, 2H), 4.07-4.17 (m, 1H), 4.34-4.45 (m, 1H), 5.10 (q, J=7.2 Hz, 1H), 6.42 (br. s., 1H), 7.07-7.15 (m, 1H), 7.15-7.21 (m, 1H), 7.36 (s, 1H), 7.39 (d, J=1.0 Hz, 1H), 7.50 (s, 1H), 8.14 (br. s., 1H). MS (ES+): m/z=491.15/493.15 (100/50) [MH+]. HPLC: tR=1.41 min (polar—3 min, UPLC-ACQUITY).

Provenance & Evidence