Methyl iodide → HCID 10050637, compound

Participants

Reaction Steps

To a solution of 6-[(4-chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-4-(5-methyl-thiophen-2-yl)-1H-quinolin-2-one (115 mg, 0.248 mmol) in THF (6.6 ml) was added a 40% aqueous NaOH (3.3 ml), benzyltriethylammonium chloride (28 mg. 0.124 mmol) and a solution of methyl iodide (0.017 ml, 0.273 mmol) in THF (0.05 ml). The reaction mixture was stirred at ambient temperature for 1.5 hours after which time it was partitioned between ethyl acetate and 10% aqueous potassium carbonate. The organic layer was washed with brine, dried over MgSO4 and concentrated under vacuum to give the crude product. It was chromatographed on silica gel with MeOH—CHCl3—NH4 (1:99:0.1) as eluents to afford the title compound as a white solid (68 mg, 0.143 mmol, 58% yield).

Provenance & Evidence