Sodium Carbonate → HCID 67111220, compound

HRID 2363205Notes

Reaction equation

HRID 2363205 reaction equation
Br[C:2]1[O:6][C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:4][CH:3]=1.[F:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][C:14]=1[C:22]([F:25])([F:24])[F:23].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O>[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:2]2[O:6][C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:4][CH:3]=2)=[CH:15][C:14]=1[C:22]([F:23])([F:24])[F:25]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 345282Ethyl 5-bromofuran-2-carboxylateHCID 177500514-Fluoro-3-(trifluoromethyl)benzeneboronic acid

Product 1

HCID 67111220HCID 67111220, compoundYield 83.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of ethyl 5-bromofuran-2-carboxylate (150 mg, 0.69 mmol) in DME (5 mL) were added 4-fluoro-3-(trifluoromethyl)phenylboronic acid (171 mg, 0.82 mmol), 2M Na2CO3 (1.03 mL, 2.06 mol), and catalytic amounts of Pd(Ph3)4 (158 mg, 0.14 mmol). The reaction mixture was refluxed for 5 h, 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 (174 mg, 70%).

Workup

  1. temperatureThe reaction mixture was refluxed for 5 h
  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-46881bbc54d0484fbbbab19f5331b17d
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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