Ethyl 3-phenylprop-2-enoate → 3-(6-Methoxy-1H-Indol-4-yl)-3-phenyl-acrylic acid ethyl ester

HRID 1716692Notes

Reaction equation

Br[C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[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>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:24]([O:23][C:13](=[O:22])[CH:14]=[C:15]([C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[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

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-bromo-6-methoxy-indole CXIV (920 mg, 4.1 mmol), ethyl cinnamate (1.03 ml, 6.1 mmol), TEA (850 μl, 6.1 mmol), Pd(OAc)2 (46 mg, 0.20 mmol) and (o-Tol)3P (120 mg, 0.41 mmol) was heated in a sealed vial to 100° C. for 27 hours; The reaction mixture was cooled to room temperature, diluted with DCM, and the mixture was filtered through celite. The filtrate was concentrated and purified via flash chromatography (hexane/EtOAc) to afford 3-(6-methoxy-1H-Indol-4-yl)-3-phenyl-acrylic acid ethyl ester CXVI as a yellow-brown waxy solid (440 mg, 34% yield).

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationthe mixture was filtered through celite
concentrationThe filtrate was concentrated
custompurified via flash chromatography (hexane/EtOAc)

Sources & evidence

ORD record: ord-8ec1051f90f84aa9b37030d9ef963e02
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07803830B2

Reaction notes

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