Methanol → 5-[4,6-Difluoro-5-(1-methyl-1H-indol-5-yl)-1H-benzoimidazol-2-yloxy]-2-methyl-benzoic acid

Participants

Reaction Steps

A solution of 5-[4,6-difluoro-5-(1-methyl-1H-indol-5-yl)-1H-benzoimidazol-2-yloxy]-2-methyl-benzoic acid methyl ester (655 mg, 1.464 mmol) in THF:MeOH:H2O (7 mL) was treated with sodium hydroxide (1N, 3 mL) at room temperature. After 3 h, another 3 mL of sodium hydroxide (1N) was added and stirred at room temperature for another 1.5 h, and at 50° C. for another 1.5 h. The cooled reaction solution was concentrated on a rotavapor and the resulting aqueous solution was neutralized with 1N hydrogen chloride (6 mL), and the resulting white solid was collected through filtration (washed with water) and dried under high vacuum to give the desired product as a white solid. LC-MS: calculated for C24H17F2N3O3 434.41, observed m/e 434.6 (M+H)+ (Rt 1.52 min). 1H NMR (300 MHz, DMSO-d6): δ 7.78-7.15 (m, 8H), 6.45 (d, J=3.3 Hz, 1H), 3.81 (s, 3H), 2.53 (s, 3H).

Provenance & Evidence