Triethylamine → methyl 4-chloro-2-(2-(3-(methoxycarbonyl)phenyl)acetamido)-5-(1-methyl-1H-indol-5-yl)benzoate

Participants

Reaction Steps

To a solution of methyl 2-amino-4-chloro-5-(1-methyl-1H-indol-5-yl)benzoate (Intermediate 45) (150 mg, 0.477 mmol) in dichloromethane (10 mL) was added {3-[(methyloxy) carbonyl]phenyl}acetic acid (Akos, 97 mg, 0.500 mmol), HATU (236 mg, 0.620 mmol) and triethylamine (0.073 mL, 0.524 mmol) and the reaction mixture was stirred at room temperature overnight. The mixture was washed with water and brine, the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Purification by flash chromatography using cyclohexane to cyclohexane/ethyl acetate 80:20 as eluant gave the title compound methyl 4-chloro-2-(2-(3-(methoxycarbonyl)phenyl)acetamido)-5-(1-methyl-1H-indol-5-yl)benzoate (205 mg, 0.418 mmol, 88% yield) as a white amorphous solid. LCMS: (M+H)+=491; Rt=4.19 min.

Provenance & Evidence