Potassium Carbonate → 2,2,2-Trifluoro-1-{5-[4-(methylthio)phenyl]-2-thienyl}ethanone

HRID 1715353Notes

Reaction equation

HRID 1715353 reaction equation
Br[C:2]1[S:6][C:5]([CH:7]([OH:12])[C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[CH3:13][S:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>CCO.O>[F:9][C:8]([F:11])([F:10])[C:7]([C:5]1[S:6][C:2]([C:18]2[CH:19]=[CH:20][C:15]([S:14][CH3:13])=[CH:16][CH:17]=2)=[CH:3][CH:4]=1)=[O:12]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27339594-(Methylthio)phenylboronic acidHCID 199715801-(5-Bromothiophen-2-yl)-2,2,2-trifluoroethanol

Product 1

HCID 685063682,2,2-Trifluoro-1-{5-[4-(methylthio)phenyl]-2-thienyl}ethanone

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1-(5-Bromo-4-thienyl)-1,2,2-trifluoroethanol (C1) in DUE added to Polymer-Bound Triphenylphosphine Pd(0) (0.5% eq) followed by 4-(methylthio)phenylboronic acid (1.3 eq)) in EtOH and K2CO3 (1.5 eq) in water and the mixture was stirred at 75° C. for 24 h. The suspension was filtered and the filtrate was purified by reverse phase HPLC as described for Example 3. MS (ES) C13H9F3OS2 requires: 302, found: 303 (M+H+).

Workup

  1. filtrationThe suspension was filtered
  2. customthe filtrate was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-b6dfb07dd3dc4b89844fa94670232d83
Source dataset
uspto-grants-2010_09
Patent number
US07799825B2

Reaction notes

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