Triethylborane → HCID 22911835, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-((3,5-dichlorophenoxy)methyl)-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)thiazole (Example 33) (0.508 g, 1.0 mmol) in THF (5 mL) at 0° C. under nitrogen was added 2.0M n-butyl magnesium chloride in THF (1.6 mL, 3.2 mmol) slowly, via syringe, and the mixture stirred at 0° C. for 30 minutes and then at room temperature (25° C.) for 2 hours. After cooling to 0° C., a 1.0M solution of triethyl borane in THF (5 mL, 5 mmol) was added and the mixture was warmed to room temperature and stirred for 2 hours, and then heated to reflux for 36 hours. After cooling to room temperature and stirring for 3 hours, water (3 mL) was added followed by sodium acetate (1.2 g) and hydroxylamine-O-sulfonic acid (0.82 g). After stirring at room temperature overnight, the mixture was poured into 3 volumes of ethyl acetate, and the organic layer washed with water and brine and dried over MgSO4. After solvent removal, the white solids (a mixture of product and starting material) were purified by flash chromatography on silica gel using 30% ethyl acetate/70% hexane to provide 4-[4-(4-fluorophenyl)-2-((3,5-dichlorophenoxy)methyl)-5-thiazolyl]benzenesulfonamide as a white solid (0.147 g): Anal. Calc'd for C22H15N2O3S2FCl2 : C, 51.87; H, 2.97; N, 5.50. Found: C, 52.19; H, 2.84; N, 5.40

Provenance & Evidence