1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-butyl 2-(5-isopropyl-2,4-bis(4-methoxybenzyloxy)-N-(1-methyl-1H-indol-5-yl)benzamido)acetate

Participants

Reaction Steps

tert-butyl 2-(1-methyl-1H-indol-5-ylamino)acetate (1) and 5-isopropyl-2,4-bis(4-methoxybenzyloxy)benzoic acid were dissolved in dichloromethane at room temperature. 1-Ethyl-3-(3-dimethylaminopropyl)-carbodiimide (EDC) was added to the reaction solution and stirred for 2 hours. Work-up with water and extracted with dichloromethane followed by drying and concentration produced tert-butyl 2-(5-isopropyl-2,4-bis(4-methoxybenzyloxy)-N-(1-methyl-1H-indol-5-yl)benzamido)acetate (2). Without further purification, compound 2 was treated with Lawesson's reagent in toluene at 100° C. produced tert-butyl 2-(5-isopropyl-2,4-bis(4-methoxybenzyloxy)-N-(1-methyl-1H-indol-5-yl)phenylthioamido)acetate (3) in 82% over 2 steps.

Provenance & Evidence