Sodium Carbonate → 2-(4-Trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester

HRID 2363201Notes

Reaction equation

HRID 2363201 reaction equation
Br[C:2]1[S:3][C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:6]=1.[F:12][C:13]([F:24])([F:23])[C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:12][C:13]([F:24])([F:23])[C:14]1[CH:19]=[CH:18][C:17]([C:2]2[S:3][C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:6]=2)=[CH:16][CH:15]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 3614103Ethyl 2-bromothiazole-5-carboxylate

Product 1

HCID 210512492-(4-Trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl esterYield 35.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of ethyl 2-bromothiazole-5-carboxylate (39 μl, 0.26 mmol) in toluene (2 mL) were added 4-(trifluoromethyl)phenylboronic acid (60 mg, 0.32 mmol), 2M Na2CO3(390 μl, 0.78 mmol), and catalytic amounts of Pd(PPh3)4 (61 mg, 0.05 mmol). The reaction mixture was refluxed for 6 hrs, diluted with water and extracted with EtOAc. The extracts were washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by column chromatography on silica gel (EtOAc/n-Hex=1:5) to give title compound (28 mg, 30%).

Workup

  1. temperatureThe reaction mixture was refluxed for 6 hrs
  2. extractionextracted with EtOAc
  3. washThe extracts were washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified by column chromatography on silica gel (EtOAc/n-Hex=1:5)

Sources & evidence

ORD record
ord-bce351a243e443da99061ca3bf0876e5
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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