Methyl iodide → N-[2-(2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-ylethynyl)-phenyl]-N-methyl-methanesulfonamide

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Reaction Steps

189 c) To a suspension of N-[2-(2-chloro-[1,2,4]triazolo[1,5-a]pyridin-8-ylethynyl)-phenyl]-methanesulfonamide (900.0 mg, 2.595 mmol) and cesium carbonate (950.0 mg, 2.916 mmol) in acetonitrile (5 mL) was added iodomethane (0.25 mL, 4.0 mmol). The reaction flask was capped and the mixture was stirred at room temperature over weekend. The volatiles were evaporated. The recovered solid was triturated with water (30 mL), filtered and rinsed with water then was dissolved in dichloromethane (50 mL) and was separated. The organic layer was dried over magnesium sulfate, filtered and evaporated. N-[2-(2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-ylethynyl)-phenyl]-N-methyl-methanesulfonamide was isolated as a tan solid (0.871 g, 93%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.51 (d, J=6.7 Hz, 1H), 7.78 (d, J=7.4 Hz, 1H), 7.68 (d, J=7.6 Hz, 1H), 7.52 (d, J=7.8 Hz, 1H), 7.46 (t, J=7.4 Hz, 1H), 7.38 (t, J=7.5 Hz, 1H), 7.10 (t, J=7.1 Hz, 1H), 3.54 (s, 3H), 3.21 (s, 3H). MS=361, 363 (MH)+.

Provenance & Evidence