6-Ethenyl-1-[3-fluoro-4-(methyloxy)phenyl]-4-(methyloxy)-1H-indole → 6-Ethyl-1-[3-fluoro-4-(methyloxy)phenyl]-4-(methyloxy)-1H-indole

HRID 2421234Notes

Reaction equation

HRID 2421234 reaction equation
[CH:1]([C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][N:9]2[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([F:20])[CH:13]=2)=[C:5]([O:21][CH3:22])[CH:4]=1)=[CH2:2]>C(O)C.C(OCC)(=O)C.[Pd]>[CH2:1]([C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][N:9]2[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([F:20])[CH:13]=2)=[C:5]([O:21][CH3:22])[CH:4]=1)[CH3:2]

Participants

5

Reactant 1

HCID 671364536-Ethenyl-1-[3-fluoro-4-(methyloxy)phenyl]-4-(methyloxy)-1H-indole

Product 1

HCID 596279376-Ethyl-1-[3-fluoro-4-(methyloxy)phenyl]-4-(methyloxy)-1H-indoleYield 89.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6-ethenyl-1-[3-fluoro-4-(methyloxy)phenyl]-4-(methyloxy)-1H-indole (D9) (200 mg, 0.67 mmol) in ethanol (7 mL) and ethyl acetate (7 mL) was hydrogenated in an H-cube over a 10% palladium on charcoal catalyst. The resulting solution was concentrated and the product purified by silica gel chromatography eluting with 5-70% dichloromethane in hexane to yield the title compound (D10), (180 mg).

Workup

  1. concentrationThe resulting solution was concentrated
  2. customthe product purified by silica gel chromatography
  3. washeluting with 5-70% dichloromethane in hexane

Sources & evidence

ORD record
ord-2712d8473fd74af9a496334741d3cacb
Source dataset
uspto-grants-2011_06
Patent number
US07956083B2

Reaction notes

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