5-[(2,4-Dichlorophenyl){5-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}methyl]-2,2-dimethyl-1,3-dioxane-4,6-dione → Ethyl 3-(2,4-dichlorophenyl)-3-{5-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propanoate

HRID 561400Notes

Reaction equation

HRID 561400 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([C:20]1[C:28]2[C:23](=[C:24]([CH2:30][S:31][CH3:32])[CH:25]=[C:26]([F:29])[CH:27]=2)[NH:22][CH:21]=1)[CH:10]1C(=O)O[C:13](C)([CH3:17])[O:12][C:11]1=[O:19]>N1C=CC=CC=1.C(O)C.[Cu]>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([C:20]1[C:28]2[C:23](=[C:24]([CH2:30][S:31][CH3:32])[CH:25]=[C:26]([F:29])[CH:27]=2)[NH:22][CH:21]=1)[CH2:10][C:11]([O:12][CH2:13][CH3:17])=[O:19]

Participants

5

Reactant 1

HCID 583923405-[(2,4-Dichlorophenyl){5-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}methyl]-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 58392475Ethyl 3-(2,4-dichlorophenyl)-3-{5-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propanoate

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

2.8 mg (0.05 mmol) of copper powder were added to 3.10 g of the compound from Example 18A with a purity of 68% (4.23 mmol) in 34 ml of pyridine and 8 ml of ethanol. The reaction mixture was heated under reflux for 1 h. It was concentrated, and the crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient) to result in 1.52 g (82% of theory) of the title compound.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 1 h
  3. concentrationIt was concentrated
  4. customthe crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-6371772ed0bb413cb62699628432924b
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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