Sodium Hydroxide → HCID 59267786, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 5-{[6-chloro-5-(2-naphthyl)-1H-benzimidazol-2-yl]oxy}-2-methylbenzoate in MeOH (3 mL) was added NaOH (2.5 M in water) (0.5 mL, 1 mmol). The mixture was heated at 50° C. and monitored by LC-MS. When the reaction was complete, it was partitioned between EtOAc and 2 M aqueous HCl. The aqueous phase was extracted with EtOAc. The combined organics were washed with brine, dried (MgSO4), filtered, and concentrated. Purification by reverse phase HPLC eluting with MeCN:H2O afforded the title compound as a white solid. LC-MS: calculated for C25H17ClN2O3 428.87, observed m/e 429.5 (M+H)+ (Rt 2.19 min). 1H NMR (500 MHz, CD3OD): δ 7.92-7.84 (m, 5H), 7.58-7.54 (m, 1H), 7.53 (s, 1H), 7.52-7.48 (m, 2H), 7.46-7.39 (m, 3H), 2.62 (s, 3H).

Provenance & Evidence