Ethyl 3-(5-methoxy-2-methylindol-3-yl)-4,4,4-trifluoro-2-butenoate → Ethyl 3-(5-methoxy-2-methylindol-3-yl)-4,4,4-trifluorobutanoate

HRID 1451526Notes

Reaction equation

HRID 1451526 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[C:6]2[C:13]([C:20]([F:23])([F:22])[F:21])=[CH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].[H][H]>CCO.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[C:6]2[CH:13]([C:20]([F:23])([F:22])[F:21])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

5

Reactant 2

HCID 53700575Ethyl 3-(5-methoxy-2-methylindol-3-yl)-4,4,4-trifluoro-2-butenoateHCID 178418361HCID 178418361, compound

Product 1

HCID 19974941Ethyl 3-(5-methoxy-2-methylindol-3-yl)-4,4,4-trifluorobutanoateYield 99.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of the indole from Step 2 (23 g, 70 mmol) in 200 mL EtOH was treated with 60 psi hydrogen over 5% palladium on carbon (2.3 g) in a Parr shaker for 18 h. The mixture was filtered through celite and evaporated to give 23 g of the title compound.

Workup

  1. filtrationThe mixture was filtered through celite
  2. customevaporated

Sources & evidence

ORD record
ord-6883df0baedb4a2aa5c1d00ee59d930d
Source dataset
uspto-grants-1997_02
Patent number
US05604253

Reaction notes

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