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

HRID 561401Notes

Reaction equation

HRID 561401 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]([CH2:29][S:30][CH3:31])[CH:24]=[C:25]([F:28])[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]([CH2:29][S:30][CH3:31])[CH:24]=[C:25]([F:28])[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 583924625-[(4-Chlorophenyl){5-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}methyl]-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 58392141Ethyl 3-(4-chlorophenyl)-3-{5-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propanoate

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

2.0 mg (0.03 mmol) of copper powder were added to 2.21 g (3.08 mmol) of the compound from Example 19A with a purity of 64% in 23 ml of pyridine and 6 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 1.29 g (82% of theory) of the title compound with a purity of 79%.

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-ce366fb6bb43415886d1d74039c4025a
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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