Methylhydrazine → HCID 87303967, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 8-methyl-6-(pyridin-3-yl)imidazo[1,2-a]pyridine-3-carbaldehyde (Intermediate 5, 80 mg, 0.337 mmol) in ethanol (10 mL) was added methyl hydrazine (0.035 mL, 0.675 mmol) at RT. The reaction mixture was heated at 80° C. for 4 hours. Ethanol was evaporated. Pyridine (5 mL) was added to this residue, followed by addition 2-methyl-5-fluoro benzene sulfonylchloride (105 mg, 0.506 mmol). The reaction mixture was stirred at RT overnight. Pyridine was evaporated. Water was added to this residue and extracted with dichloromethane. Organic layer was dried over sodium sulfate and evaporated.The crude product was purified by column chromatography (silica gel, 1.5% methanol in chloroform) to obtain the title compound. Yield: 50 mg (27%); 1H NMR (CDCl3; 300 MHz): δ 9.41(s, 1H), 8.59 (s, 1H), 8.71 (d, 1H, J=3.9 Hz), 7.99 (s, 1H), 7.97 (m, 1H), 7.94 (s, 1H), 7.66 (dd, 1H, J=8.4, 2.7 Hz), 7.47 (m, 1H), 7.43 (s, 1H), 7.21 (m, 1H), 7.07 (m, 1H), 3.47 (s, 3H), 2.73 (s, 3H), 2.53 (s, 3H); MS: m/z 438 (M+1)+.

Provenance & Evidence