Sodium Carbonate → methyl 3-cyclohexyl-2-(2-vinylphenyl)1H-indole-6-carboxylate

HRID 1518215Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)=[C:10](Br)[NH:11]2)=[CH:7][CH:6]=1)=[O:4].[CH:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1B(O)O)=[CH2:22].C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCOCC1>[CH:15]1([C:9]2[C:8]3[C:12](=[CH:13][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=3)[NH:11][C:10]=2[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[CH:21]=[CH2:22])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

Conditions

Temperature: 110 °C

Procedure

2-bromo-3-cyclohexyl indole-6-carboxylic acid methyl ester (1 eq., prepared as described in WO 2004/087714) was mixed with 2-vinyl benzene boronic acid (1.6 eq.) and bis(triphenylphosphine)palladium dichloride (0.15 eq.) was added. The mixture was degassed and dioxane and 2M aqueous sodium carbonate solution (5 eq.) were added. The mixture was heated under nitrogen atmosphere to 110° C. After 2 h all volatiles were removed in vacuo and the residual material was subjected to flash chromatography (PE:EtOAc, 10:1). After evaporation of the solvent the product was obtained as yellow crystals (83%). MS (ES+): 360.4 (M+H+).

Workup

additionwas added
customThe mixture was degassed
customAfter 2 h all volatiles were removed in vacuo
customAfter evaporation of the solvent the product

Sources & evidence

ORD record: ord-8e41e63642ec4fe29d6d99d4495e47bb
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232390B2

Reaction notes

Loading…