Ethyl Acetate → Ethyl 3-(4-chlorophenyl)-4-(methylsulfanyl)-1h-indole-2-carboxylate

HRID 857318Notes

Reaction equation

HRID 857318 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[S:17]([CH3:19])=O)[N:10]3CCCC(CC(O)=O)C=23)=[CH:4][CH:3]=1.[CH3:28][CH2:29][O:30][C:31]([CH3:33])=[O:32]>[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[S:17][CH3:19])[NH:10][C:33]=2[C:31]([O:30][CH2:29][CH3:28])=[O:32])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 21867520(+/-)-[10-(4-Chlorophenyl)-1-(methylsulfinyl)-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-yl]acetic acid

Product 1

HCID 21867418Ethyl 3-(4-chlorophenyl)-4-(methylsulfanyl)-1h-indole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of the indole of step 3 (2.1 g) in 200 mL of EtOAc was added 5% palladium on carbon (1 g). The mixture was shaken under H2 atmosphere (50 psi) for 24 hours, filtered on a silica gel pad eluted with EtOAc and the filtrate concentrated to give the title compound as a white solid (1.5 g) used as such.

Workup

  1. filtrationfiltered on a silica gel pad
  2. washeluted with EtOAc
  3. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-cc1c75be34d14fffbf44e42c708dcd7a
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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