Sodium Iodide → [5-fluoro-(4-methanesulfonyl-2-trifluoromethyl-benzyl)-2-methyl-1H-indol-3-yl]-acetic acid ethyl ester

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Reaction Steps

To a stirring solution of (5-fluoro-2-methyl-1H-indol-3-yl)-acetic acid ethyl ester (100 mg, 0.43 mmol) in dry DMSO (2 ml) at room temperature, is added sodium hydride (26 mg, 0.65 mmol) as a 60% dispersion in mineral oil. After stirring at room temperature for 30 mins, 1-bromomethyl-4-methanesulfonyl-2-trifluoromethyl-benzene (216 mg, 0.68 mmol) (intermediate 1c) and sodium iodide (102 mg, 0.68 mmol) are added. The reaction mixture is stirred at room temperature for 60 h. The reaction mixture is poured into water (20 ml) and extracted with EtOAc (20 ml). The organic phase is dried (MgSO4) and evaporated to dryness in vacuo. The crude product is purified by reverse phase chromatography on a C18 Isolute™ cartridge, eluting in 0-100% MeCN in water, using a FlashMaster Personal™ and GradMaster™; [M+H]+ 472.

Provenance & Evidence