Sodium Chloride → HCID 59177869, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5.00 g (29.7 mmol) of methyl (2-fluorophenyl)acetate in 80 ml of THF is added dropwise to a 1 N solution of LiHMDS in hexane (35.7 ml, 35.7 mmol) cooled to −78° C. The mixture is stirred at −78° C. for 1 h and then 6.28 g (35.7 mmol) of 2-chloronicotinoyl chloride are added, and the mixture is stirred for a further hour. It is warmed to RT, and saturated ammonium chloride solution is added. The mixture is diluted with water and extracted with diethyl ether. The organic phase is dried over sodium sulfate and concentrated in vacuo. The residue is dissolved in 24 ml of DMSO, and 0.95 g (52.7 mmol) of water and 1.70 g (29.0 mmol) of sodium chloride are added. The solution is heated in 8 portions at 150° C. for 10 min in each case. It is then diluted with water and extracted with tert-butyl methyl ether. The organic phase is dried over sodium sulfate and concentrated in vacuo. The residue is purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 2:1). 3.00 g (46% of theory) of the desired compound are obtained.

Provenance & Evidence