Water → 1H-Pyrrolo[2,3-B]pyridine-3-carboxaldehyde, 5-chloro-1-(phenylsulfonyl)-

HRID 509967노트

반응식

HRID 509967 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([CH:11]=[O:12])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[OH-].[K+].[C:15]1([S:21](Cl)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>ClCCl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[C:15]1([S:21]([N:8]2[C:5]3=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=[C:4]3[C:10]([CH:11]=[O:12])=[CH:9]2)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 468564775-chloro-1H-pyrrolo(2,3-b)pyridine-3-carbaldehyde

생성물 1

HCID 497590321H-Pyrrolo[2,3-B]pyridine-3-carboxaldehyde, 5-chloro-1-(phenylsulfonyl)-수율 36%

시약·촉매·용매 2

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 6344Dichloromethane용매

실험 절차

To 5-chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (114, 3.60 g, 19.9 mmol) in 100 mL of dichloromethane, potassium hydroxide (50 mL, 9M aqueous, 0.45 mol), tetrabutylammonium hydrogen sulfate (400 mg, 1.0 mmol) and benzenesulfonyl chloride (11, 2.9 mL, 23.0 mmol) were added. The reaction was stirred at room temperature for 3 hours, then poured into water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was washed with ethyl acetate to provide the desired compound as a white solid (115, 2.3 g).

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under vacuum
  5. washThe resulting material was washed with ethyl acetate

출처 및 근거

ORD 기록
ord-9d346830d1ad46c6bb50bca627a4a20a
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096593B2

반응 노트

불러오는 중…