Sodium Iodide → [1-(4-methanesulfonyl-2-trifluoromethyl-benzyl)-2-methyl-1H-indol-3-yl]-acetic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of (2-methyl-1H-indol-3-yl)-acetic acid methyl ester (2.0 g, 10.5 mmol) in dry DMF (25 ml) at 0° C., is added portionwise NaH (0.46 g, 11.5 mmol) as a 60% dispersion in mineral oil. The reaction mixture is stirred at 0° C. for 1.5 h then NaI (1.72 g, 11.5 mmol) and 1-bromomethyl-4-methanesulfonyl-2-trifluoromethyl-benzene (3.65 g, 11.5 mmol) are added. The reaction mixture is stirred at room temperature for 16 h. The reaction mixture is poured into water (100 ml) and EtOAc (50 ml) is added. An emulsion is formed which is filtered. Brine (20 ml) is added to the filtrate and the organic phase is separated and dried (MgSO4). Evaporation in vacuo affords a brown oil. Purification by flash chromatography on silica gel using 5:1 iso-hexane:EtOAc, increasing polarity up to 3:1 iso-hexane:EtOAc, gives the desired product; [M+H]+ 440.

Provenance & Evidence