Acetonitrile → 6-Bromo-7-methylimidazo[1,2-a]pyridine-3-carbaldehyde

반응식

Br[CH:2]([CH:5]=[O:6])[CH:3]=O.[Br:7][C:8]1[C:9]([CH3:15])=[CH:10][C:11]([NH2:14])=[N:12][CH:13]=1.C(#N)C>>[Br:7][C:8]1[C:9]([CH3:15])=[CH:10][C:11]2[N:12]([C:2]([CH:5]=[O:6])=[CH:3][N:14]=2)[CH:13]=1

참가 물질

반응물 3

HCID 6342Acetonitrile

HCID 749452-Bromopropanedial

HCID 8176952-Amino-5-bromo-4-methylpyridine

생성물 1

HCID 467391706-Bromo-7-methylimidazo[1,2-a]pyridine-3-carbaldehyde수율 79.81%

실험 절차

Bromomalonaldehyde (5000 mg, 26.74 mmol) was added to a solution of 5-bromo-4-methylpyridin-2-amine in acetonitrile (5250 mg, 34.76 mmol). The reaction mixture was refluxed for 2 hours. After completion of the reaction, the reaction mixture was quenched with sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. The organic layer was concentrated in vacuum and the product was purified by column chromatography using ethyl acetate-petroleum ether gradient to obtain the title compound. Yield: 79.81%; 1H NMR (DMSO-d6; 300 MHz): δ 9.90 (s, 1H), 9.52 (s, 1H), 8.51 (s, 1H), 7.94 (s, 1H), 2.50 (s, 3H); MS (m/z): 239 (M+1)+.