Benzenesulfonyl chloride → HCID 45270766, 화합물

HRID 273314

반응식

HRID 273314 반응식
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.[C:12]1([S:18](Cl)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CCCCCC.CS(C)=O>[C:12]1([S:18]([N:3]2[C:11]3[C:6](=[N:7][CH:8]=[CH:9][CH:10]=3)[CH:5]=[CH:4]2)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

6

반응물 3

HCID 7369Benzenesulfonyl chlorideHCID 92264-AzaindoleHCID 24758Sodium hydride

생성물 1

HCID 45270766HCID 45270766, 화합물수율 83%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8058Hexane용매

실험 절차

Sodium hydride (60% in mineral oil, 203 mg, 5.08 mmol) was washed twice with hexane, and the residue suspended in DMSO (5 ml). 1H-Pyrrolo[3,2-b]pyridine (500 mg, 4.24 mmol) was added and the reaction stirred for 15 minutes. Benzenesulphonyl chloride (749 mg, 4.42 mmol) was added rapidly and the reaction stirred for 0.5 h. After quenching with water the product was extracted into EtOAc, dried (Na2SO4) and concentrated in vacuo. Chromatography (EtOAc, silica) yielded the title compound as a white crystalline solid (903 mg, 83%). δH (d6-DMSO) 8.48 (1H, dd, J 0.8, 3.8 Hz), 8.31 (1H, m), 8.15 (1H, d, J 3.8 Hz), 8.04 (2H, m), 7.72 (1H, m,), 7.61 (2H, m,), 7.36 (1H, dd, J 4.7, 8.4 Hz), 6.98 (1H, dd, J 0.8, 3.8 Hz). LCMS (ES+) RT 3.056 minutes, 259 (M+H)+.

후처리

  1. stirringthe reaction stirred for 0.5 h
  2. customAfter quenching with water the product
  3. extractionwas extracted into EtOAc
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-7afaea33b9224b6aba0d9aaf3a6888a7
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456286B2

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