3-(propan-2-yl)-1H-indole → HCID 58975178, compound

HRID 737062Notes

Reaction equation

HRID 737062 reaction equation
[CH:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1)([CH3:3])[CH3:2].CC(C)([O-])C.[K+].[F:19][C:20]1[CH:39]=[CH:38][C:23]([CH2:24][NH:25][C:26]([C:28]2[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=2)=[O:27])=[CH:22][CH:21]=1.C(OC(C)=O)C.O>CN(C=O)C>[F:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:24][NH:25][C:26](=[O:27])[C:28]2[CH:33]=[CH:32][C:31]([S:34]([N:6]3[C:7]4[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5]3)(=[O:35])=[O:36])=[CH:30][CH:29]=2)=[CH:38][CH:39]=1

Participants

6

Reactant 4

HCID 125348243-(propan-2-yl)-1H-indoleHCID 22728543Water ethylacetateHCID 23665647Potassium tert-butoxideHCID 589751254-(4-Fluoro-benzylcarbamoyl)-benzenesulfonyl chloride

Product 1

HCID 58975178HCID 58975178, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Stir a mixture of 3-isopropyl indole in dry DMF (20 ml) under N2 add potassium t-butoxide 1.0 M (1.2 ml, 1.2 mmol) dropwise. Stir the resulting solution for 30 minutes at ambient temperature. Add 4-(4-Fluoro-benzylcarbamoyl)-benzenesulfonyl chloride (0.360 g, 1.1 mmol) portionwise and stir the resulting mixture overnight. Pour the reaction mixture into a mixture of EtOAc—H2O. Separate the EtOAc layer, extract with H2O wash with brine and dry (MgSO4). Filter and evaporate to give the crude product. Chromatograph on the ISCO eluting with hexane-EtOAc to give a white solid (0.150 g). Mass spectrum (m/e) (M+H) 451.1492; found 451.1488.

Workup

  1. stirringStir the resulting solution for 30 minutes at ambient temperature
  2. additionPour the reaction mixture
  3. customSeparate the EtOAc layer
  4. extractionextract with H2O
  5. washwash with brine
  6. dry with materialdry (MgSO4)
  7. filtrationFilter
  8. customevaporate
  9. customto give the crude product
  10. washChromatograph on the ISCO eluting with hexane-EtOAc

Sources & evidence

ORD record
ord-6e6db808672844b2aa9b6035559abfb4
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

Loading…