Sodium hydride → HCID 118468050, compound

Participants

Reaction Conditions

Reaction Steps

A solution of NaH (18 mg, 0.46 mmol) in THF (2.0 ml) was cooled to −20° C. To this was added a solution of (4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-4-methylthiazolidin-2-one (100 mg, 0.304 mmol) in THF (1.0 ml) dropwise at the same temperature. The reaction was allowed to warm to −10° C. over 1 hour. A solution of (3-chloro-6-(trifluoromethyl)pyridin-2-yl)methyl methanesulfonate (106 mg, 0.364 mmol) in THF (1.0 ml) was added via syringe. Stirring of the reaction was continued at −10° C. for 5 hours. The reaction was quenched by addition of ice water and diluted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated. The compound was purified by column chromatography to yield (4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-3-((3-chloro-6-(trifluoromethyl)pyridin-2-yl)methyl)-4-methylthiazolidin-2-one. 1H NMR (500 MHz, CDCl3): δ 7.91 (d, J=8.2 Hz, 1H); 7.89 (s, 1H); 7.85 (s, 2H); 7.64 (d, J=8.3 Hz, 1H); 5.36 (d, J=17.5 Hz, 1H); 5.24 (d, J=6.9 Hz, 1H); 4.54-4.55 (m, 1H); 4.37 (d, J=17.5 Hz, 1H); 0.99 (d, J=6.6 Hz, 4H).

Provenance & Evidence