Sodium hydride → HCID 10548672, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 280 mg (1.0 mmol) of 5-hydroxy-1-(phenylmethyl)-1H-indole-3-acetamide in 30 mL of DMSO and 10 mL of THF was treated with 45 mg (1.1 mmol) of 60% NaH/mineral oil, and then with 0.16 mL (1.1 mmol) of ethyl 4-bromobutyrate. The mixture was heated in an oil bath at 60° C. for 2.25 hours. It was diluted with water, extracted with EtOAc, the EtOAc solution washed with water, saturated NaCl solution, dried (Na2SO4), and concentrated at reduced pressure. The residue was chromatographed on silica (CH2Cl2→3% MeOH/CH2Cl2)to give 260 mg (66% yield) of 4-[[3-(2-amino-2-oxoethyl)-1-(phenylmethyl)-1H-indol-5-yl]oxy]butanoic acid ethyl ester.

Provenance & Evidence