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

HRID 401450

反応式

HRID 401450 の反応式
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

参加物

4

反応物 3

HCID 6342AcetonitrileHCID 749452-BromopropanedialHCID 8176952-Amino-5-bromo-4-methylpyridine

生成物 1

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

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-6d8c8ba4621b4fc49b9ec3657cfabb8b
出典データセット
uspto-grants-2014_06
特許番号
US08741932B2

関連ノート

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