HCID 59267736, compound → HCID 45256690, compound

Participants

Reaction Steps

To a 0° C. suspension of 5-{[5-(4-acetylphenyl)-6-chloro-1H-benzimidazol-2-yl]oxy}-2-methylbenzoic acid (52 mg, 0.124 mmol) and CeCl3 (244 mg, 0.988 mmol) in THF (4 mL) was added MeMgBr (1.4 M in THF) (0.618 mL, 0.865 mmol) dropwise via syringe. The reaction was stirred at rt for 30 min, diluted with Et2O (50 mL) and washed with 1 M HCl (10 mL). The aqueous phase was extracted with Et2O. The combined organics were washed with H2O and brine, dried (Na2SO4), filtered and concentrated. Purification by reverse phase HPLC eluting with MeCN:H2O afforded the desired product as an off-white solid. LC-MS: calculated for C24H21ClN2O4 436.89, observed m/e 437.2 (M+H)+ (Rt: 1.81 min). 1 H NMR (500 MHz, CD3OD): δ 7.89 (d, 1H), 7.54 (d, 2H), 7.49 (s, 1H), 7.47-7.39 (m, 2H), 7.37 (m, 2H), 7.32 (s, 1H), 2.62 (s, 3H), 1.57 (s, 6H).

Provenance & Evidence