Piperidine → HCID 86693524, compound

Participants

Reaction Conditions

Reaction Steps

To a pressure tube was added 4,4-difluoro-9-iodo-4,5-dihydrobenzo[b]pyrazolo[1,5-d][1,4]oxazepine-2-carboxamide (65 mg, 0.17 mmol) followed by piperidine (1.5 ml), tetrakis(triphenylphosphine)palladium (0) (19.2 mg, 0.02 mmol), copper(I) iodide (3.2 mg, 0.02 mmol) and (2R)-2-(5-methyl-1,2-oxazol-3-yl)but-3-yn-2-ol (38 mg, 0.25 mmol). The reaction vessel was sealed and heated at 60° C. for 40 minutes. The reaction mixture was cooled and concentrated in vacuo. and then co-evaporated with dichloromethane (2×10 ml). The crude material was purified by FCC (silica, 1-8% methanol in dichloromethane) to provide 34 mg (49%) of the title compound as a pale brown solid. 1H-NMR (500 MHz, DMSO-d6): 1.81 (3H, s), 2.41 (3H, d, J=0.7 Hz), 4.85 (2H, t, J=11.7 Hz), 6.36 (1H, d, J=0.8 Hz), 6.56 (1H, s), 7.33 (1H, d, J=8.4 Hz), 7.35 (1H, s), 7.43 (1H, dd, J=8.4, 2.0 Hz), 7.60 (1H, s), 8.16 (1H, s), 8.37 (1H, d, J=2.0 Hz); M+23=437.

Provenance & Evidence