Pyridine → HCID 86613310, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture consisting of (1-{3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-4-phenyl-isoxazol-5-yl}-cyclopropyl)-methanol (Example 1, Compound E, 2.0 g) in dichloromethane (30 mL) is added sequentially pyridine (0.60 mL), methanesulfonyl chloride (0.55 mL), and 4-dimethylaminopyridine (0.06 g) at 0° C. under a nitrogen atmosphere. The mixture is stirred at 0° C. for 30 minutes and is warmed to room temperature. The mixture is stirred at room temperature for four hours and is then diluted with dichloromethane (30 mL.) The mixture is washed 0.5 N hydrochloric acid solution and with brine solution. The organic layer is separated, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The concentrate is purified by flash silica gel column chromatography to afford the synthetic intermediate methanesulfonic acid 1-{3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-4-phenyl-isoxazol-5-yl}-cyclopropylmethyl ester (2.35 g.)

Provenance & Evidence