Triethylamine → 7-(1-Azidoethyl)-5-chloro-8-(2-fluorophenyl)quinoline

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Reaction Steps

To a mixture of 1-[5-chloro-8-(2-fluorophenyl)quinolin-7-yl]ethanol (0.044 g, 0.14 mmol) in methylene chloride (0.9 mL) was added triethylamine (0.0305 mL, 0.219 mmol), followed by methanesulfonyl chloride (0.0141 mL, 0.182 mmol). After stirring at room temperature for 30 minutes, the resultant mixture was diluted with dichloromethane, washed with saturated sodium bicarbonate and brine, dried over magnesium sulfate, and then concentrated to dryness under reduced pressure. The resulting residue was used directly in next step. LCMS (M+H)+m/z=380.0. The crude mesylate was dissolved in N,N-dimethylformamide (0.4 mL) and treated with sodium azide (0.0474 g, 0.730 mmol) at 60° C. for 1 hour. After diluting with ethyl acetate, the mixture was washed with water and brine and then dried over magnesium sulfate and evaporated to dryness. The crude product was used in the next step. LCMS calculated for C17H13ClFN4(M+H)+: m/z=327.1; found: 327.0.

Provenance & Evidence