Sodium hydride → HCID 68579531, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-naphthalen-1-ylmethyl-1H-indole-2-carboxylic acid ethyl ester (170 mg, from Exp. 64.2.) in dimethylformamide (1.0 ml) was added NaH (1.3 eq.), the mixture was stirred at 22° C. for 30 min. 1-Bromo-2-methoxy-ethane (99 mg) was added, the mixture was stirred for 17 h and partitioned between aqueous NH4Cl and AcOEt. The organic layer was dried, evaporated and the residue was chromatographed on silica (n-heptane/AcOEt, 20:1) to give 1-(2-methoxy-ethyl)-3-naphthalen-1-ylmethyl-1H-indole-2-carboxylic acid ethyl ester which was hydrolyzed as described in the general procedure B (Exp. 2.2) to give the title compound as a white semisolid. MS: 358.1 ([M−H]−).

Provenance & Evidence