2-Propenoic acid, 3-(1H-indol-3-yl)-, ethyl ester → 3-(1H-Indol-6-yl)-3-(1H-indol-3-yl)-acrylic acid ethyl ester

HRID 1716636Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:16])[CH:5]=[CH:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)[CH3:2].Br[C:18]1[CH:26]=[C:25]2[C:21]([CH:22]=[CH:23][NH:24]2)=[CH:20][CH:19]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:16])[CH:5]=[C:6]([C:18]1[CH:26]=[C:25]2[C:21]([CH:22]=[CH:23][NH:24]2)=[CH:20][CH:19]=1)[C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)[CH3:2]

Participants

Conditions

Temperature: 114 °C

Procedure

A sealed tube flushed with N2 was charged with 3-(1H-indol-3-yl)-acrylic acid ethyl ester (323 mg, 1.5 mmol), 6-bromoindole (196 mg, 1 mmol), tetra-butylammonium bromide (64.4 mg, 0.2 mmol), TEA (209 μl, 1.5 mmol) and palladium-dichloro-[bis(tri-ortho-tolyl)phosphine] (39.3 mg, 0.05 mmol). The mixture was stirred at 114° C. for 1 hour, cooled to room temperature, dissolved in DCM, and purified via flash chromatography (hexane/EtOAc) to afford 3-(1H-indol-6-yl)-3-(1H-indol-3-yl)-acrylic acid ethyl ester XXVI (250 mg, yellow oil) as a mixture of geometric isomers.

Workup

customA sealed tube flushed with N2
temperaturecooled to room temperature
custompurified via flash chromatography (hexane/EtOAc)

Sources & evidence

ORD record: ord-122144b2bd7645caae5bd09f56f306c9
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07803830B2

Reaction notes

Loading…