Potassium Iodide → (6-{[5-(4-Trifluoromethyl-phenyl)-pent-4-ynoylamino]-methyl}-indol-1-yl)-acetic acid ethyl ester

HRID 751229Notes

Reaction equation

HRID 751229 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:10][NH:11][C:12](=[O:27])[CH2:13][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)[CH:8]=2)[CH:3]=[CH:2]1.[CH2:28]([O:30][C:31](=[O:34])[CH2:32]Br)[CH3:29].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>C(#N)C>[CH2:28]([O:30][C:31](=[O:34])[CH2:32][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:10][NH:11][C:12](=[O:27])[CH2:13][CH2:14][C:15]#[C:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:24])([F:26])[F:25])=[CH:19][CH:18]=3)[CH:8]=2)[CH:3]=[CH:2]1)[CH3:29]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 860955295-(4-Trifluoromethyl-phenyl)-pent-4-ynoic acid (1H-indol-6-ylmethyl)-amide

Product 1

HCID 68826130(6-{[5-(4-Trifluoromethyl-phenyl)-pent-4-ynoylamino]-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], 5-(4-trifluoromethyl-phenyl)-pent-4-ynoic acid (1H-indol-6-ylmethyl)-amide 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 off-white crystals.

Sources & evidence

ORD record
ord-d23197b345144107af32d8370cae5f9e
Source dataset
uspto-grants-2008_07
Patent number
US07405236B2

Reaction notes

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