Triethylamine → HCID 58368505, compound

Participants

Reaction Steps

To a mixture of 1-[4-chloro-7-(3-fluorophenyl)-2,1-benzisoxazol-6-yl]ethanol (0.094 g, 0.32 mmol) in methylene chloride (2 mL) was added triethylamine (0.067 mL, 0.48 mmol), followed by methanesulfonyl chloride (0.031 mL, 0.40 mmol). After stirring at room temperature for 30 minutes, the resulting mixture was diluted with dichloromethane, washed with sat. sodium bicarbonate, brine, dried over magnesium sulfate, and then concentrated to dryness under reduced pressure. The resulting 1-[4-chloro-7-(3-fluorophenyl)-2,1-benzisoxazol-6-yl]ethyl methanesulfonate was used directly in the next step. LCMS calculated for C16H14ClFNO4S (M+H)+: m/z=370.0; Found: 370.1. The crude mesylate was dissolved in N,N-dimethylformamide (1 mL) and treated with sodium azide (0.105 g, 1.61 mmol) at room temperature overnight. After diluted with ethyl acetate, the mixture was washed with water, brine and then dried over magnesium sulfate and evaporated to dryness. The crude product was used in the next step (90 mg, 88%). LCMS calculated for C15H11ClFN4O (M+H)+: m/z=317.1; Found: 317.0.

Provenance & Evidence