Dimethylformamide → 1-(Phenylsulfonyl)-1H-pyrrolo(2,3-b)pyridine-2-carboxaldehyde

HRID 2196712ノート

反応式

HRID 2196712 の反応式
C([Li])CCC.[C:6]1([S:12]([N:15]2[C:19]3=[N:20][CH:21]=[CH:22][CH:23]=[C:18]3[CH:17]=[CH:16]2)(=[O:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CN([CH:27]=[O:28])C.[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[C:6]1([S:12]([N:15]2[C:19]3=[N:20][CH:21]=[CH:22][CH:23]=[C:18]3[CH:17]=[C:16]2[CH:27]=[O:28])(=[O:14])=[O:13])[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 8520781-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridineHCID 178418339Butyllithium

生成物 1

HCID 566921991-(Phenylsulfonyl)-1H-pyrrolo(2,3-b)pyridine-2-carboxaldehyde収率 62%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-78 °C

実験手順

n-Butyllithium (11.9 mL, 19.0 mmol, 1.6M in hexanes) was added to a solution of 1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (3.50 g, 13.6 mmol) in THF (53 mL) at −78° C. The reaction mixture was stirred at −78° C. for 30 minutes, and then DMF (4.2 mL, 54.2 mmol) was added. The reaction mixture was warmed up to 0° C. and stirred for 3 hours. It was then treated with saturated aqueous ammonium chloride and ethyl acetate, and the layers were separated. The aqueous layer was extracted with ethyl acetate. The organic layer was dried with sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography to afford 1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde (2.4 g, 62%) as a solid.

後処理

  1. temperatureThe reaction mixture was warmed up to 0° C.
  2. stirringstirred for 3 hours
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography

出典と根拠

ORDレコード
ord-d96289c7411c4e3d93f63f29daae4447
出典データセット
uspto-grants-2012_12
特許番号
US08338452B2

反応ノート

読み込み中…