Piperidine → HCID 86693526, compound

Participants

Reaction Conditions

Reaction Steps

To a pressure tube was added 9-iodo-4,5-dihydrobenzo[b]pyrazolo[1,5-d][1,4]oxazepine-2-carboxamide (99 mg, 0.28 mmol) followed by piperidine (2.0 mL), tetrakis(triphenylphosphine)palladium (0) (32 mg, 0.03 mmol), copper(I) iodide (5 mg, 0.03 mmol) and (2R)-2-(5-methyl-1,2-oxazol-3-yl)but-3-yn-2-ol (63 mg, 0.42 mmol). The reaction vessel was sealed and heated at 60° C. for 30 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, 2-8% methanol in dichloromethane) to provide 59 mg (56%) of the title compound as a pale brown solid. 1H NMR (DMSO, 500 MHz) δ 1.80 (3H, s), 2.41 (3H, s), 3.17 (2H, t, J=5.8 Hz), 4.49 (2H, t, J=5.8 Hz), 6.32-6.39 (1H, m), 6.52 (1H, s), 6.72 (1H, s), 7.21 (1H, d, J=8.4 Hz), 7.34 (1H, s), 7.37 (1H, dd, J=8.4, 2.1 Hz), 7.79 (1H, s), 8.02 (1H, d, J=2.1 Hz); M+23=401.

Provenance & Evidence