Potassium Iodide → {6-[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-ylmethoxy]-indol-1-yl}-acetic acid tert-butyl ester

HRID 1767947Notes

Reaction equation

HRID 1767947 reaction equation
[C:1]([O:5][C:6](=[O:18])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=2)[CH:10]=[CH:9]1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:20][C:21]1[N:22]=[C:23]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=2)[S:24][C:25]=1[CH3:26].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>CC(C)=O>[C:1]([O:5][C:6](=[O:18])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:20][C:21]3[N:22]=[C:23]([C:27]4[CH:28]=[CH:29][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:31][CH:32]=4)[S:24][C:25]=3[CH3:26])[CH:15]=2)[CH:10]=[CH:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 236145004-(Bromomethyl)-5-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazoleHCID 69283069tert-Butyl (6-hydroxy-1H-indol-1-yl)acetate

Product 1

HCID 69279699{6-[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-ylmethoxy]-indol-1-yl}-acetic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In analogy to the procedure described in example 1 a], (6-hydroxy-indol-1-yl)-acetic acid tert-butyl ester (example 6 b]) was reacted with 4-bromomethyl-5-methyl-2-(4-trifluoromethyl-phenyl)-thiazole in the presence of cesium carbonate and potassium iodide in acetone for 72 h at ambient temperature to give the title compound as colorless oil.

Sources & evidence

ORD record
ord-498fe07b51ad44579be64ef6e859f1ef
Source dataset
uspto-grants-2007_06
Patent number
US07235572B2

Reaction notes

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