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

HRID 2196712노트

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HRID 2196712 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d96289c7411c4e3d93f63f29daae4447
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338452B2

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