1,2-Dichloroethane → 2-(3-Chloro-phenyl)-imidazo[1,2-a]pyridine-7-carboxylic acid (tetrahydro-pyran-4-ylmethyl)-amide

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Reaction Steps

To a solution of 2-(3-chloro-phenyl)-imidazo[1,2-a]pyridine-7-carboxylic acid sodium salt (141 mg, 0.481 mmol) in DMF (2 mL) were added EDC (3 eq, 1.44 mmol, 277 mg) and HOBt (3 eq, 1.44 mmol, 195 mg). The mixture was stirred at room temperature for 15 minutes then tetrahydropyran-methylamine (1.5 eq, 0.72 mmol, 83 mg) and triethyl amine (3 eq, 1.44 mmol, 0.21 mL) were added. The reaction mixture was stirred at room temperature for 3 hours then quenched by the addition of water. The product was extracted three times with ethyl acetate and the crude product was purified by column chromatography to afford 2-(3-chloro-phenyl)-imidazo[1,2-a]pyridine-7-carboxylic acid (tetrahydro-pyran-4-ylmethyl)-amide in 65% yield. 1H NMR (DMSO-d6) δ 8.69 (1H), 8.61 (2H), 8.16 (1H), 8.11 (1H), 7.98 (1H), 7.51 (1H), 7.41 (1H), 7.38 (1H), 3.92 (2H), 3.18 (2H), 3.11 (2H), 1.95 (1H), 1.31 (2H), 1.12 (2H); m/z (M+H)=370.3

Provenance & Evidence