Methyl Acrylate → HCID 54059723, compound

HRID 1716640Notes

Reaction equation

HRID 1716640 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[C:11]([O:15][CH3:16])(=[O:14])[CH:12]=[CH2:13]>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:16][O:15][C:11](=[O:14])[CH:12]=[CH:13][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7294Methyl AcrylateHCID 6764936-Bromoindole

Product 1

HCID 54059723HCID 54059723, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a resealable reaction tube was added 6-bromoindole (5 g, 26 mmol), methyl acrylate (2.9 ml, 32 mmol), TEA (4.4 ml, 32 mmol), (o-Tol)3P (0.78 g, 2.6 mmol) and Pd(OAc)2 (0.29 g, 1.3 mmol). The reaction tube was sealed and the resulting mixture was stirred at 100° C. for 20 hours, then cooled to room temperature, diluted with DCM, and filtered through celite. The filter cake was washed with DCM. The filtrate was concentrated and purified via flash chromatography (hexane/EtOAc) to provide 3-(1H-indol-6-yl)-acrylic acid methyl ester XXX (3.8 g, 73% yield) as a bright yellow solid.

Workup

  1. customThe reaction tube was sealed
  2. temperaturecooled to room temperature
  3. filtrationfiltered through celite
  4. washThe filter cake was washed with DCM
  5. concentrationThe filtrate was concentrated
  6. custompurified via flash chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-0eb544c59e8f45928fa3b7bff83daace
Source dataset
uspto-grants-2010_09
Patent number
US07803830B2

Reaction notes

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