(2S)-But-3-yn-2-ol → HCID 178462270, compound

Participants

Reaction Steps

A solution of N-({3-[(3-bromo-5-chlorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)-4-chloro-1H-imidazole-5-carboxamide (86 mg, 0.174 mmol), (2S)-3-butyn-2-ol (30.5 mg, 0.436 mmol), palladiumbisdichlorobistriphenylphosphine (12.23 mg, 0.017 mmol), copper(I) iodide (1.659 mg, 8.71 μmol) and TEA (0.121 ml, 0.871 mmol) in THF (3 ml) was irradiated in the microwave for 10 minutes at 120° C. The reaction mixture was diluted with EtOAc and washed with water. The solvent was removed and the crude material was purified via reverse phase HPLC to give 4-chloro-N-{[4-chloro-3-({3-chloro-5-[(3S)-3-hydroxy-1-butyn-1-yl]phenyl}oxy)-2-fluorophenyl]methyl}-1H-imidazole-5-carboxamide (37 mg, 0.077 mmol, 44% yield). 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.54-7.94 (m, 1H), 7.26-7.47 (m, 2 H), 7.11 (s, 1H), 6.89 (s, 1H), 6.74 (s, 1H), 4.24-4.71 (m, 3H), 1.41 (d, 3H). LC-MS (ES+) m/z 481.95, [M+H].

Provenance & Evidence