Hydrochloric Acid → {1-[4-(Cyclohexyl-methyl-sulfamoyl)-benzyl]-5-fluoro-2-methyl-1H-indol-3-yl}-acetic acid

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Reaction Steps

To a stirring suspension of (5-fluoro-2-methyl-1H-indol-3-yl)-acetic acid ethyl ester (100 mg, 0.43 mmol) in dry DMSO (1 ml), is added NaH (29 mg, 0.73 mmol). The reaction mixture is stirred at room temperature for 15 min after which time 4-bromomethyl-N-cyclohexyl-N-methyl-benzenesulfonamide (149 mg, 0.43 mmol) is added. Reaction mixture is diluted with water (10 ml) and treated with 1N HCl aq to acidic pH. The product is extracted in 1:1 EtOAc:Et2O (20 ml), washed with brine, dried (MgSO4) and evaporated in vacuo. The crude reaction mixture is purified by preparative MS-directed HPLC to afford the title compound; [M+H]+ 474.

Provenance & Evidence