3-(4-Chlorophenyl)-4-(methylsulfanyl)-1h-indole-2-carboxylic acid → 3-(4-Chlorophenyl)-1h-indol-4-yl methyl sulfide

HRID 857320Notes

Reaction equation

HRID 857320 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][CH3:18])[NH:10][C:9]=2C(O)=O)=[CH:4][CH:3]=1>N1C2C(=CC=CC=2)C=CC=1.[Cu]>[CH3:18][S:17][C:15]1[C:16]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)=[CH:9][NH:10][C:11]=2[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 218674693-(4-Chlorophenyl)-4-(methylsulfanyl)-1h-indole-2-carboxylic acid

Product 1

HCID 218674683-(4-Chlorophenyl)-1h-indol-4-yl methyl sulfideYield 62.2%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7047QuinolineSolvent

Procedure

To a solution of 1.4 g of the acid of Step 5 in quinoline (10 mL) was added 100 mg of copper powder. The reaction mixture was heated to reflux and stirred for 2 hours. The copper powder was removed by filtration and 6N HCl was added to the filtrate. The aqueous layer was extracted with EtOAc and the combined organic layers were dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography eluted with 10% EtOAc in Hexanes to provide 750 mg of the title compound as an orange solid foam.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. customThe copper powder was removed by filtration and 6N HCl
  4. additionwas added to the filtrate
  5. extractionThe aqueous layer was extracted with EtOAc
  6. dry with materialthe combined organic layers were dried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography
  9. washeluted with 10% EtOAc in Hexanes

Sources & evidence

ORD record
ord-4b325d8d83d14537ac7866120097b3d6
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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