Ethyl isocyanate → HCID 68578198, compound

Participants

Reaction Steps

To a solution 5-fluoro-3-hydroxymethyl-1-naphthalen-1-ylmethyl-1H-indole-2-carboxylic acid ethyl ester (51 mg, from Example 95) in dichloromethane (0.5 ml) was added 10 mg of ethyl isocyanate and stirring was continued at 22° C. for 16 h. 4-Dimethylaminopyridine (17 mg) was added and stirring was continued at 22° C. for 4 days. The mixture was chromatographed on silica using n-heptane/AcOEt (1:1) to give 3-ethylcarbamoyloxymethyl-5-fluoro-1-naphthalen-1-ylmethyl-1H-indole-2-carboxylic acid ethyl ester as a colorless solid. MS: 471.3 ([M+Na]+). The product was dissolved in EtOH (1 ml), diluted with 1N aqueous NaOH (0.187 ml) and the mixture was heated to 45° C. for 1 h. The mixture was acidified with AcOH and purified by HPLC (RP-18, CH3CH/H2O, gradient) to give 3-ethoxymethyl-5-fluoro-1-naphthalen-1-ylmethyl-1H-indole-2-carboxylic acid as a white solid. MS: 376.5 ([M−H]−).

Provenance & Evidence