4-Methylmorpholine → 2,3-Dihydro-1-[(4'-fluoro[1,1'-biphenyl]-4-yl)sulfonyl]-(2S)-1H-indole-2-carboxylic acid methyl ester

Participants

Reaction Steps

A mixture of 0.545 g (2.55 mmol) of the hydrochloride of the methyl ester of 2,3-dihydro-(2S)-1H-indole-2-carboxylic acid and 10 ml of acetonitrile is prepared and 0.9 g (3.32 mmol) of 4′-fluoro[1,1′-biphenyl]-4-sulfonyl chloride and 0.62 ml of N-methylmorpholine are added. The reaction mixture is stirred for 16 hours at room temperature and then concentrated under reduced pressure. The residue is taken up in 100 ml of ethyl acetate and washed with 3 times 75 ml of water. The organic phase is dried over magnesium sulfate and then concentrated under reduced pressure. The crude product is purified by chromatography on silica gel using a toluene/ethyl acetate mixture (98/2; v/v) as the eluent to give 0.83 g of the expected compound in the form of a white solid (yield=79%).

Provenance & Evidence