Iodobenzene → ethyl 2,3-dimethyl-1-phenyl-1H-indole-5-carboxylate

HRID 1015439Notes

Reaction equation

[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH3:11])=[CH:8][C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=2.I[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C@@H]1(N)CCCC[C@H]1N>C1(C)C=CC=CC=1.[Cu]I>[CH3:1][C:2]1[N:3]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:4]2[C:9]([C:10]=1[CH3:11])=[CH:8][C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=2

Participants

Conditions

Temperature: 100 °C

Procedure

A 234 mg portion of ethyl 2,3-dimethyl-1H-indole-5-carboxylate was dissolved in 1 ml of toluene, and 0.145 ml of iodobenzene and 10 mg of copper(I) iodide and 480 mg of tripotassium phosphate and 26 ml of trans-1,2-cyclohexanediamine were added at room temperature, followed by stirring at 100° C. for 24 hours. After evaporation of the solvent under a reduced pressure, the residue was purified by silica gel column chromatography (hexane-ethyl acetate:hexane=1:4) to obtain 79 mg of ethyl 2,3-dimethyl-1-phenyl-1H-indole-5-carboxylate as a colorless oily material.

Workup

customAfter evaporation of the solvent under a reduced pressure
customthe residue was purified by silica gel column chromatography (hexane-ethyl acetate:hexane=1:4)

Sources & evidence

ORD record: ord-6738724c5ef7496086a2d4fe3ddb77b7
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07985764B2

Reaction notes

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