Methyl 4-(Chlorosulfonyl)benzoate → HCID 58975020, compound

HRID 736982Notes

Reaction equation

HRID 736982 reaction equation
CC(C)([O-])C.[K+].[CH:7]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1)([CH3:9])[CH3:8].[CH3:19][O:20][C:21](=[O:32])[C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.C(OC(C)=O)C.O>CN(C=O)C.CCCCCC.CCOC(C)=O>[CH3:19][O:20][C:21](=[O:32])[C:22]1[CH:23]=[CH:24][C:25]([S:28]([N:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:10]([CH:7]([CH3:9])[CH3:8])=[CH:11]2)(=[O:29])=[O:30])=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 4738388Methyl 4-(Chlorosulfonyl)benzoateHCID 125348243-(propan-2-yl)-1H-indoleHCID 22728543Water ethylacetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 58975020HCID 58975020, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Add potassium tert butoxide 1.0 M (1.6 mL, 0.0016 mol) dropwise to a stirring solution of 3-isopropyl indole (0.217 g, 00136 mol) in dry DMF (20 mL) under N2 at ambient temperature. Stir the reaction mixture for 30 minutes and add portionwise 4-chlorosulfonyl benzoic acid methyl ester (0.328 g, 0.0014 mol). The light brown reaction mixture decolorizes immediately. Stir the resulting yellow solution overnight. Pour into a EtOAc—H2O mixture (100 to 300 mL). Separate the EtOAc and sequentially extract with H2O (3×250 mL), wash with brine, dry (MgSO4), filter and evaporate giving 0.38 g. Chromatograph on the ISCO using a gradient hexane-EtOAc (0-50%, 30 30 minutes) to give 0.249 g (51%) of the title compound as a waxy solid. Mass spectrum (m/e) (M+H) 358.1113. found (M+H) 358.1129.

Workup

  1. stirringStir the resulting yellow solution overnight
  2. customSeparate the EtOAc
  3. extractionsequentially extract with H2O (3×250 mL)
  4. washwash with brine
  5. dry with materialdry (MgSO4)
  6. filtrationfilter
  7. customevaporate
  8. customgiving 0.38 g

Sources & evidence

ORD record
ord-51075de71dd443a683313cac638ae469
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

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