Methyl 2-(2,2,2-trifluoroacetamido)imidazo[1,2-a]pyridine-6-carboxylate → HCID 59233078, compound

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Reaction Conditions

Reaction Steps

To a stirred solution of compound 1B (470 mg, 1.64 mmol) in anhydrous THF (20 mL) were portion wise added lithium aluminum hydride (155 mg, 4.09 mmol) at 0° C. After being stirred for 1 h at 0° C., the reaction was quenched with 0.16 mL of water, followed by 0.16 mL of 15% NaOH and 0.48 mL of water. The heterogenous reaction mixture was stirred for 0.5 h at room temperature and then filtered through celite. Residue was washed with THF. Filtrate and washings were concentrated and the crude residue was purified by column chromatography to furnish compound 1C (220 mg, 52%). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.41 (s, 1H), 8.52 (s, 1H), 8.21 (s, 1H), 7.47 (d, J=9.2 Hz, 1H), 7.25 (d, J=9.6 Hz, 1H), 5.36 (t, J=5.6 Hz, 1H) 4.48 (d, J=5.6 Hz, 2 H) ESI-MS:m/z 260.2 (M+H)+.

Provenance & Evidence