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

HRID 401450

反应方程式

HRID 401450 反应方程式
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

参与物

4

反应物 3

HCID 6342乙腈HCID 749452-溴丙二醛HCID 8176952-氨基-5-溴-4-甲基吡啶

产物 1

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

实验过程

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)+.

后处理

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. customAfter completion of the reaction
  3. customthe reaction mixture was quenched with sodium bicarbonate solution
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationThe organic layer was concentrated in vacuum
  8. customthe product was purified by column chromatography

来源与证据

ORD记录
ord-6d8c8ba4621b4fc49b9ec3657cfabb8b
来源数据集
uspto-grants-2014_06
专利号
US08741932B2

关联笔记

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