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

HRID 736980Notes

Reaction equation

HRID 736980 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-0dea3151871241489e90aa87c1b82c56
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

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