Ethyl bromoacetate → {3-Ethyl-5-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-indol-1-yl}-acetic acid ethyl ester

HRID 1767963Notes

Reaction equation

HRID 1767963 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)[S:5][C:6]=1[CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37].Cl.O.[CH2:43]1COC[CH2:44]1>C(OCC)C>[CH2:39]([O:38][C:36](=[O:37])[CH2:35][N:14]1[C:15]2[C:11](=[CH:10][C:9]([O:8][CH2:7][C:6]3[S:5][C:4]([C:18]4[CH:19]=[CH:20][C:21]([C:24]([F:27])([F:25])[F:26])=[CH:22][CH:23]=4)=[N:3][C:2]=3[CH3:1])=[CH:17][CH:16]=2)[C:12]([CH2:43][CH3:44])=[CH:13]1)[CH3:40]

Participants

7

Reactant 5

HCID 7748Ethyl bromoacetateHCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 21885828Hydrate;hydrochlorideHCID 219494915-({4-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methoxy)-1H-indole

Product 1

HCID 69279669{3-Ethyl-5-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-indol-1-yl}-acetic acid ethyl esterYield 98%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A suspension of 5-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-1H-indole (485 mg, 1.16 mmol), cesium carbonate (1.38 g, 3.49 mmol) and ethyl bromoacetate (0.15 ml, 1.28 mmol) in THF (5 ml) was stirred for 1.5 h at ambient temperature. Diethyl ether and 1N HCl/water 1/1 were added. The ether phase was dried over sodium sulfate and concentrated under reduced pressure to give 635 mg (1.26 mmol, 98%) {3-ethyl-5-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-indol-1-yl}-acetic acid ethyl ester.

Workup

  1. dry with materialThe ether phase was dried over sodium sulfate
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2ef9cd4b7fa64eef88b7934da5d7487e
Source dataset
uspto-grants-2007_06
Patent number
US07235572B2

Reaction notes

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