Propyne → HCID 178439241, compound

Participants

Reaction Steps

To a solution of N-({3-[(3-bromo-5-cyanophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)-4-chloro-1H-imidazole-5-carboxamide (70.0 mg, 0.145 mmol), Palladium dichlorobistriphenylphosphine(II) (7.55 mg, 0.014 mmol), copper(I)iodide (1.377 mg, 7.23 μmol) and TEA (0.101 ml, 0.723 mmol) in THF (4 ml) was bubbled 1-propyne (11.59 mg, 0.289 mmol) for 5 minutes and the reaction mixture was irradiated in a personal microwave reactor for 10 minutes at 120° C. The solvent was removed and the crude material was purified via reverse phase HPLC to give 4-chloro-N-[(4-chloro-3-{[3-cyano-5-(1-propyn-1-yl)phenyl]oxy}-2-fluorophenyl)methyl]-1H-imidazole-5-carboxamide (29 mg, 0.065 mmol, 45% yield). 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.60-7.81 (m, 1H), 7.40 (s, 1H), 7.28-7.38 (m, 3H), 7.16 (s, 1H), 7.05 (s, 1H), 4.62 (s, 2H), 1.99 (s, 3H). LC-MS (ES+) m/z 443.13, [M+H].

Provenance & Evidence