Bromine → HCID 57812632, compound

Participants

Reaction Steps

To a solution of 4-(4-{6-amino-7-[(R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-furo[3,2-c]pyridin-3-yl}-pyrazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (400 mg, 0.68 mmol) in anhydrous DCM (10 mL) was added a solution of bromine (430 mg, 2.7 mmol) in DCM (3 mL). The resulting mixture was stirred at rt for 30 min. The mixture was quenched with sat. aq. Na2S2O3 (15 mL) and diluted with DCM (50 mL), then washed with brine (20 mL), and dried over anhydrous sodium sulfate. Evaporation afforded a yellow residue, which was purified by silica gel chromatography (Hex.-EtOAc=30:70→100% EtOAc) to give the title compound as a light-yellow solid. LC-MS (ES+): 668.01/669.99/671.97 [MH+]. 1H NMR (CDCl3, 400 MHz): δ 1.49 (s, 9H), 1.90 (d, J=6.8 Hz, 3H), 1.95-2.04 (m, 2H), 2.18-2.21 (m, 2H), 2.93 (m, 2H), 4.31-4.38 (m, 3H), 5.19 (br s, 2H), 6.54 (q, J=6.6 Hz, 1H), 7.08 (dd, J=8.8, 8.0 Hz, 1H), 7.30 (dd, J=8.8, 4.8 Hz, 1H), 7.85 (s, 1H), 7.94 (s, 1H), 8.05 (s, 1H).

Provenance & Evidence