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

HRID 561409Notes

Reaction equation

HRID 561409 reaction equation
[Br:1][C:2]1[S:3][C:4]([CH:7]([C:18]2[C:26]3[C:21](=[C:22]([CH2:27][S:28][CH3:29])[CH:23]=[CH:24][CH:25]=3)[NH:20][CH:19]=2)[CH:8]2C(=O)O[C:11](C)([CH3:15])[O:10][C:9]2=[O:17])=[CH:5][N:6]=1>N1C=CC=CC=1.C(O)C.[Cu]>[Br:1][C:2]1[S:3][C:4]([CH:7]([C:18]2[C:26]3[C:21](=[C:22]([CH2:27][S:28][CH3:29])[CH:23]=[CH:24][CH:25]=3)[NH:20][CH:19]=2)[CH2:8][C:9]([O:10][CH2:11][CH3:15])=[O:17])=[CH:5][N:6]=1

Participants

5

Reactant 1

HCID 583922715-[(2-Bromo-1,3-thiazol-5-yl){7-[(methylsulfanyl)methyl]-1H-indol-3-yl}methyl]-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 58392201Ethyl 3-(2-bromo-1,3-thiazol-5-yl)-3-{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propanoate

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

19 mg (0.29 mmol) of copper powder were added to 3.57 g (81% purity, 5.87 mmol) of the compound from Example 24A in 15 ml of pyridine and 8 ml of ethanol. The reaction mixture was heated under reflux for 5 h and then the copper was filtered off through kieselguhr. The filtrate was concentrated, the residue was stirred with diethyl ether/dichloromethane, and the precipitated solid was filtered off. The filtrate was concentrated and purified by preparative HPLC (acetonitrile/water gradient). 1.24 g (46% of theory) of the title compound were obtained.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 5 h
  3. filtrationthe copper was filtered off through kieselguhr
  4. concentrationThe filtrate was concentrated
  5. filtrationthe precipitated solid was filtered off
  6. concentrationThe filtrate was concentrated
  7. custompurified by preparative HPLC (acetonitrile/water gradient)

Sources & evidence

ORD record
ord-32e54ae571c748a381040f995f830c8f
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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