Potassium Iodide → (6-{[3-(4-Trifluoromethyl-phenyl)-prop-2-ynylcarbamoyl]-methyl}-indol-1-yl)-acetic acid ethyl ester

HRID 751224Notes

Reaction equation

HRID 751224 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:10][C:11]([NH:13][CH2:14][C:15]#[C:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)=[O:12])[CH:8]=2)[CH:3]=[CH:2]1.[CH2:27]([O:29][C:30](=[O:33])[CH2:31]Br)[CH3:28].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>C(#N)C>[CH2:27]([O:29][C:30](=[O:33])[CH2:31][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:10][C:11](=[O:12])[NH:13][CH2:14][C:15]#[C:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:24])([F:25])[F:26])=[CH:19][CH:18]=3)[CH:8]=2)[CH:3]=[CH:2]1)[CH3:28]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 688232462-(1H-indol-6-yl)-N-[3-(4-trifluoromethyl-phenyl)-prop-2-ynyl]-acetamide

Product 1

HCID 68822688(6-{[3-(4-Trifluoromethyl-phenyl)-prop-2-ynylcarbamoyl]-methyl}-indol-1-yl)-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In analogy to the procedure described for example 1 b], 2-(1H-indol-6-yl)-N-[3-(4-trifluoromethyl-phenyl)-prop-2-ynyl]-acetamide was reacted with bromo-acetic acid ethyl ester in the presence of cesium carbonate and potassium iodide in acetonitrile under reflux conditions to give the title compound as colorless oil.

Sources & evidence

ORD record
ord-d5eebdad483c42948aa6abd4ca01fd54
Source dataset
uspto-grants-2008_07
Patent number
US07405236B2

Reaction notes

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