Ethyl 3-phenylprop-2-enoate → 3-(7-Methoxy-1H-Indol-4-yl)-3-phenyl-acrylic acid ethyl ester

HRID 1716660Notes

Reaction equation

HRID 1716660 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[C:13]([O:23][CH2:24][CH3:25])(=[O:22])[CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[CH2:24]([O:23][C:13](=[O:22])[CH:14]=[C:15]([C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:25]

Participants

5

Reactant 2

HCID 7649Ethyl 3-phenylprop-2-enoateHCID 468355404-Bromo-7-methoxy-1H-indole

Product 1

HCID 673560833-(7-Methoxy-1H-Indol-4-yl)-3-phenyl-acrylic acid ethyl esterYield 34%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolvent

Procedure

A stirring mixture of 4-bromo-7-methoxyindole LII (162 mg, 0.717 mmol), ethyl cinnamate (254 mg, 1.43 mmol), tetra-butylammonium bromide (46 mg, 0.143 mmol), TEA (199 μl, 1.43 mmol) and palladium-dichloro-[bis-(tri-ortho-tolyl)phosphine] (28 mg, 0.036 mmol) in DMF (2 ml) was heated in a sealed vial flushed with N2, at 110° C. for 20 hours. The reaction was cooled to room temperature and partitioned between H2O and EtOAc. The organic layer was separated and the aqueous layer was extracted twice with EtOAc. The organics were combined dried over Na2SO4, filtered and evaporated. The crude mixture was purified via flash chromatography (hexane/EtOAc) affording 3-(7-methoxy-1H-Indol-4-yl)-3-phenyl-acrylic acid ethyl ester LIII (108 mg, 34% yield).

Workup

  1. temperaturewas heated in a sealed
  2. customvial flushed with N2, at 110° C. for 20 hours
  3. custompartitioned between H2O and EtOAc
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted twice with EtOAc
  6. dry with materialThe organics were combined dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude mixture was purified via flash chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-9562c5f4bc254329b8badc63961d0e68
Source dataset
uspto-grants-2010_09
Patent number
US07803830B2

Reaction notes

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