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

HRID 1242310Notes

Reaction equation

HRID 1242310 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:37])[CH2:27][S:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][C:30]=1[CH3:36])([CH3:24])([CH3:23])[CH3:22].C([O-])([O-])=O.[Cs+].[Cs+]>CC(C)=O>[C:21]([O:25][C:26](=[O:37])[CH2:27][S:28][C:29]1[CH:34]=[CH:33][C:32]([O: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[CH3:36])([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 21935947[Rac]-3-(1-chloro-ethyl)-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridineHCID 67072245(4-Hydroxy-2-methyl-phenylsulfanyl)-acetic acid tert-butyl ester

Product 1

HCID 69526547(2-Methyl-4-{1-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethoxy]-phenylsulfanyl)-acetic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 0.118 g (0.39 mmol) of the above prepared [rac]-3-(1-chloro-ethyl)-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridine (example 17C]) and 0.100 g (0.39 mmol) of (4-hydroxy-2-methyl-phenylsulfanyl)-acetic acid tert-butyl ester (see below example 20C]), dissolved in 2.0 ml of abs. acetone, were added successively 0.065 g (0.39 mmol) of KI and 0.154 g (0.47 mmol) of Cs2CO3. The reaction was allowed to proceed for 2 h at ambient temperature, when TLC still indicated large amounts of starting material. Therefore, stirring was continued over night at 40° C. Pouring onto crashed ice, extraction with AcOEt, filtration over Celite, washing of the organic layer with water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=9/1), produced 0.143 g of the title compound as colorless oil.

Workup

  1. dissolutiondissolved in 2.0 ml of abs
  2. waitwas continued over night at 40° C
  3. additionPouring
  4. extractionice, extraction
  5. filtrationwith AcOEt, filtration over Celite
  6. washwashing of the organic layer with water
  7. dry with materialdrying over sodium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-7ed52eb9620043329d78ba5c5dddc03c
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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