(R)-2-(5-methyl-1,2,4-oxadiazol-3-yl)but-3-yn-2-ol → HCID 86693522, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 9-iodo-4,5-dihydrobenzo[b]pyrazolo[1,5-d][1,4]oxazepine-2-carboxamide (100 mg, 0.28 mmol), (R)-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-but-3-yn-2-ol (70 mg, 0.46 mmol), and copper(I) iodide (10 mg, 0.05 mmol) in piperidine (1.5 ml) was sonicated under a stream of argon for 15 minutes. After the addition of tetrakis(triphenylphosphine)palladium (0) (40 mg, 0.035 mmol) the mixture was heated at 60° C. for 3 hours before the being concentrated. The residue was taken up in ethyl acetate (100 ml) and pre-absorbed onto a small amount of silica. Purification by FCC (silica, 0-10% methanol in dichloromethane) gave a solid residue, which was re-crystallised from heptane/dichloromethane (˜10 ml, 2/1). Filtration and drying of the crystalline material under high vacuum provided 53 mg (40%) of the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.83 (3H, s), 2.61 (3H, s), 3.17 (2H, t, J=5.80 Hz), 4.49 (2H, t, 0.1=5.80 Hz), 6.71 (1H, s), 6.74 (1H, s), 7.22 (1H, d, J=8.39 Hz), 7.35 (1H, s), 7.38 (1H, dd, J=8.32, 2.06 Hz), 7.81 (1H, s), 8.03 (1H, d, J=1.98 Hz); M+1=380.

Provenance & Evidence