o-Toluenesulfonyl chloride → 1-{1-[(4-Methylphenyl)sulfonyl]-1H-indol-3-yl}ethanone

HRID 736980

반응식

HRID 736980 반응식
[CH3:1][C:2]([O-])([CH3:4])[CH3:3].[K+].[C:7]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1)(=[O:9])[CH3:8].[C:19]1(C)[C:20]([S:25](Cl)(=[O:27])=[O:26])=[CH:21]C=CC=1.C(OC(C)=O)C.O>CN(C=O)C>[C:2]1([CH3:4])[CH:3]=[CH:21][C:20]([S:25]([N:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:10]([C:7](=[O:9])[CH3:8])=[CH:11]2)(=[O:27])=[O:26])=[CH:19][CH:1]=1

참가 물질

6

반응물 4

HCID 8623o-Toluenesulfonyl chlorideHCID 128023-AcetylindoleHCID 22728543Water ethylacetateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 3577941-{1-[(4-Methylphenyl)sulfonyl]-1H-indol-3-yl}ethanone수율 78%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Add 1.0 M t-BuOK (3.0 mL, 0.003 mol) to a stirring solution of 3-acetyl indole (0.478 g, 0.0030 mol) in dry DMF (20 mL) under N2 at ambient temperature and stir for 30 min. Add toluenesulfonyl chloride to this solution and stir the resulting mixture overnight. Pour the reaction into EtOAc—H2O, separate the organic layer and extract several times with H2O wash with brine, dry (MgSO4), filter, and evaporate on the rotary evaporator. Chromatograph on the ISCO eluting with a gradient hexane-EtOAc (0-100%) over 30 minutes to give 0.73 g (78%) of the title compound as a solid: 1H (CDCl3). δ 7.8 (d, 1H), 8.2 (s, 1H), 7.9 (d, 1H), 7.7 (d, 2H), 7.4 (m, 2H), 7.3 (d, 2H), 2.6 (s, 3H), 2.4 (s, 3H).

후처리

  1. additionPour
  2. customseparate the organic layer
  3. extractionextract several times with H2O
  4. washwash with brine
  5. dry with materialdry (MgSO4)
  6. filtrationfilter
  7. customevaporate on the rotary evaporator
  8. washChromatograph on the ISCO eluting with a gradient hexane-EtOAc (0-100%) over 30 minutes

출처 및 근거

ORD 기록
ord-0dea3151871241489e90aa87c1b82c56
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07595339B2

연결된 노트

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