Methyl chloroformate → HCID 21191848, compound

Participants

Reaction Steps

A solution of 0.48 g (1.64 mmol) of 2,6-dimethyl-1-(phenylmethyl)-1H-indole-3-acetic acid in 25 ml of tetrahydrofuran(THF) was cooled with an ice-water bath, 0.45 ml of triethylamine was added followed by 0.13 ml (1.7 mmol) of methyl chloroformate. After 0.5 hour, gaseous NH3 was bubbled into the reaction mixture for 0.5 hour, the cooling bath removed and the mixture stirred for 2 hours. It was then poured into water and extracted with EtOAc, the EtOAc solution washed with a Na2CO3 solution, dried(Na2SO4), and concentrated at reduced pressure. The residue was crystallized from MeOH/water, to give 0.19 g (39% yield) of 2,6-dimethyl-1-(phenylmethyl)-1H-indole-3-acetamide, mp, 160-163° C.

Provenance & Evidence