Sodium hydride → HCID 68580361, compound

Participants

Reaction Steps

To as solution of 3-naphthalen-1-ylmethyl-1H-indole-2-carboxylic acid ethyl ester (46 mg, from Example 64.2.) in dimethylformamide (1 ml) was added 8 mg of NaH (55% in oil) and stirring was continued at 22° C. for 1 h. The mixture was treated with a solution of 2-chloro-N,N-dimethylacetamide (18 mg) in dimethylformamide (0.5 ml) and stirring was continued for 16 h. The mixture was diluted with saturated aqueous NaHCO3 and extracted with ethylacetate. The organic layer was washed with brine, dried, evaporated and the residue chromatographed on silica (n-heptane/AcOEt, 3:2) to give 1-dimethylcarbamoylmethyl-3-naphthalen-1-ylmethyl-1H-indole-2-carboxylic acid ethyl ester as a colorless solid, MS: 415.4 ([M+H]+), which was hydrolyzed as described in the general procedure B (Exp. 2.2) to give the title compound as a colorless solid. MS: 385.4 ([M−H]−).

Provenance & Evidence