Cesium carbonate → (2-Methyl-4-{1-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethylsulfanyl}-phenoxy)-acetic acid tert-butyl ester

HRID 1242308Notes

Reaction equation

HRID 1242308 reaction equation
Cl[CH:2]([C:4]1[C:5]([CH3:20])=[N:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1)[CH3:3].[C:21]([O:25][C:26](=[O:40])[CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([S:35]C(=O)C)=[CH:31][C:30]=1[CH3:39])([CH3:24])([CH3:23])[CH3:22].C(OC(=O)COC1C=CC(S)=CC=1C)(C)(C)C.C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C.CO>[C:21]([O:25][C:26](=[O:40])[CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([S:35][CH:2]([C:4]2[C:5]([CH3:20])=[N:6][C:7]([C:10]3[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=3)=[CH:8][CH:9]=2)[CH3:3])=[CH:31][C:30]=1[CH3:39])([CH3:24])([CH3:23])[CH3:22]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 11572955(4-Acetylsulfanyl-2-methyl-phenoxy)-acetic acid tert-butyl esterHCID 21935947[Rac]-3-(1-chloro-ethyl)-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridineHCID 67072235(4-Mercapto-2-methyl-phenoxy)-acetic acid tert-butyl ester

Product 1

HCID 67072330(2-Methyl-4-{1-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethylsulfanyl}-phenoxy)-acetic acid tert-butyl esterYield 54.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

0.224 g (0.75 mmol) of [rac]-3-(1-chloro-ethyl)-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridine and 0.222 g (0.75 mmol) of (4-acetylsulfanyl-2-methyl-phenoxy)-acetic acid tert-butyl ester (prepared by standard acetylation of (4-mercapto-2-methyl-phenoxy)-acetic acid tert-butyl ester, described below in example 28A)-C]) were dissolved in 3.9 ml of acetonitrile and 0.2 ml of MeOH and treated with 0.292 g (1.2 eq.) of Cs2CO3. The reaction was then allowed to proceed over night. Pouring onto crashed ice, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=9/1), afforded in the less polar fractions 0.210 g of pure title compound and in the more polar fractions 0.112 g of the corresponding methyl ester as waxy solid.

Workup

  1. waitto proceed over night
  2. additionPouring
  3. extractionice, twofold extraction with AcOEt
  4. washwashing with water
  5. dry with materialdrying over sodium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-968dc1aa0be344afac3905b975d49e93
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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