Potassium Iodide → {3-Chloro-6-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-indol-1-yl}-acetic acid tert-butyl ester

HRID 1767981Notes

Reaction equation

HRID 1767981 reaction equation
[C:1]([O:5][C:6](=[O:19])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=2)[C:10]([Cl:18])=[CH:9]1)([CH3:4])([CH3:3])[CH3:2].Cl[CH2:21][C:22]1[S:26][C:25]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=2)=[N:24][C:23]=1[CH3:37].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>CC(C)=O>[C:1]([O:5][C:6](=[O:19])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:21][C:22]3[S:26][C:25]([C:27]4[CH:28]=[CH:29][C:30]([C:33]([F:36])([F:34])[F:35])=[CH:31][CH:32]=4)=[N:24][C:23]=3[CH3:37])[CH:15]=2)[C:10]([Cl:18])=[CH:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 27830065-Chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazoleHCID 69283057tert-Butyl (3-chloro-6-hydroxy-1H-indol-1-yl)acetate

Product 1

HCID 69280392{3-Chloro-6-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-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], (3-chloro-6-hydroxy-indol-1-yl)-acetic acid tert-butyl ester was reacted with 5-chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole [PCT Int. Appl. (2002), WO 0292590 A1] in the presence of cesium carbonate and potassium iodide in acetone for 14 h at ambient temperature to give the title compound as yellow crystals.

Sources & evidence

ORD record
ord-75f25b3296dc49fbb563232ece0fbbe4
Source dataset
uspto-grants-2007_06
Patent number
US07235572B2

Reaction notes

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