HCID 58392528, compound → Ethyl 3-(4-chlorophenyl)-3-{7-[(ethylsulfanyl)methyl]-1H-indol-3-yl}propanoate

HRID 561395Notes

Reaction equation

HRID 561395 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[C:27]3[C:22](=[C:23]([CH2:28][S:29][CH2:30][CH3:31])[CH:24]=[CH:25][CH:26]=3)[NH:21][CH:20]=2)[CH:9]2C(=O)O[C:12](C)([CH3:16])[O:11][C:10]2=[O:18])=[CH:4][CH:3]=1>N1C=CC=CC=1.C(O)C.[Cu]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:19]2[C:27]3[C:22](=[C:23]([CH2:28][S:29][CH2:30][CH3:31])[CH:24]=[CH:25][CH:26]=3)[NH:21][CH:20]=2)[CH2:9][C:10]([O:11][CH2:12][CH3:16])=[O:18])=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 58392528HCID 58392528, compound

Product 1

HCID 58392395Ethyl 3-(4-chlorophenyl)-3-{7-[(ethylsulfanyl)methyl]-1H-indol-3-yl}propanoateYield 93.7%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

2 mg (0.03 mmol) of copper powder were added to 1.38 g (3.00 mmol) of the compound from Example 14A in 15 ml of pyridine and 5 ml of ethanol. The reaction mixture was heated under reflux for 1 h. It was concentrated, and the residue was taken up in ethyl acetate, washed with 1N hydrochloric acid, dried over magnesium sulfate, filtered through silica gel and concentrated. 1.13 g of the target compound with a purity of 84% (78% of theory) were obtained.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 1 h
  3. concentrationIt was concentrated
  4. washwashed with 1N hydrochloric acid
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered through silica gel
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-39715f78224d47659c30411ec3ececb7
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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