5-fluoro-2-methylbenzenesulfonyl chloride

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 6-(1H-indol-2-yl)imidazo[1,2-a]pyridine-3-carbaldehyde (Intermediate 6, 115 mg, 0.3691 mmol) in ethanol (10 mL) was added methyl hydrazine (0.04 mL, 0.7395 mmol) at RT. The reaction mixture was heated at 80° C. for 4 h. Ethanol was evaporated. Pyridine (5 mL) was added to this residue, followed by addition of 2-methyl-5-fluoro benzene sulfonylchloride (0.07 mL, 0.5535 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: 28 mg (17%); 1H NMR (DMSO-d6; 500 MHz): δ 11.83 (s, 1H), 9.09 (s, 1H), 9.81 (s, 1H), 8.34 (s, 1H), 8.27 (d, 1H, J=9.5 Hz), 8.08 (d, 1H, J=9.5 Hz), 7.74 (d, 1H, J=6.5 Hz), 7.61 (d, 1H, J=8 Hz), 7.43 (m, 3H), 7.18 (t, 1H, J=8), 7.07 (t, 1H, J=7.5 Hz), 6.91 (s, 1H), 3.48 (s, 3H); MS: m/z 460 (M−1)+. Ethanol was evaporated Pyridine (5 mL) was added to this residue Pyridine was evaporated Water was added to this residue extracted with dichloromethane Organic layer was dried over sodium sulfate evaporated The crude product was purified by column chromatography (Silica gel, 1.5% methanol in chloroform)

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 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)+. Ethanol was evaporated Pyridine (5 mL) was added to this residue Pyridine was evaporated Water was added to this residue extracted with dichloromethane Organic layer was dried over sodium sulfate was purified by column chromatography (silica gel, 1.5% methanol in chloroform)