Triethylamine → 7-(1-Azidoethyl)-5-chloro-8-(3-fluorophenyl)isoquinoline

Participants

Reaction Steps

To a mixture of 1-[5-chloro-8-(3-fluorophenyl)isoquinolin-7-yl]ethanol (0.100 g, 0.331 mmol) in methylene chloride (0.6 mL) was added triethylamine (0.092 mL, 0.66 mmol) followed by methanesulfonyl chloride (0.038 mL, 0.50 mmol) at 0° C. The reaction was stirred at room temperature for 30 minutes, then diluted with dichloromethane and washed with water. The organic layers were dried over magnesium sulfate and concentrated to dryness under reduced pressure. The resulting sulfonate was used in the next step. LCMS (M+H)+380.1. To the this crude 1-[5-chloro-8-(3-fluorophenyl)isoquinolin-7-yl]ethyl methanesulfonate in N,N-dimethylformamide (0.6 mL) was added sodium azide (0.11 g, 1.6 mmol). The reaction was stirred at room temperature for 1 hour, then quenched with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and evaporated to dryness to provide crude desired azide (0.105 mg, 97%). LCMS calculated for C17H13ClFN4 (M+H)+: m/z=327.1; Found: 327.1.

Provenance & Evidence