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5-([2-Chloro-4-(trifluoromethyl)phenyl]{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione → Ethyl 3-[2-chloro-4-(trifluoromethyl)phenyl]-3-{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propanoate

HRID 561435
Notes
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Reaction equation

HRID 561435 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[CH:12]([C:23]1[C:31]2[C:26](=[C:27]([CH2:32][S:33][CH3:34])[CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1)[CH:13]1C(=O)O[C:16](C)([CH3:20])[O:15][C:14]1=[O:22]>N1C=CC=CC=1.C(O)C.[Cu]>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:5]=[CH:4][C:3]=1[CH:12]([C:23]1[C:31]2[C:26](=[C:27]([CH2:32][S:33][CH3:34])[CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1)[CH2:13][C:14]([O:15][CH2:16][CH3:20])=[O:22]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 1

HCID 583922325-([2-Chloro-4-(trifluoromethyl)phenyl]{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 58392306Ethyl 3-[2-chloro-4-(trifluoromethyl)phenyl]-3-{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propanoate

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 702EthanolSolvent
HCID 1049
Pyridine
Solvent

Procedure

2.8 mg (45 μmol) of copper powder were added to a solution of 3.64 g (approx. 5.12 mmol, 72% purity) of the compound from Example 93A in 41 ml of pyridine and 10 ml of ethanol. The reaction mixture was heated under reflux overnight. It was concentrated, and the crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient) to result in 1.34 g (57% of theory) of the title compound.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux overnight
  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-feed547c7ab940adb4616938dfb78879
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08063234B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes