Sodium Carbonate → HCID 53412006, compound

HRID 1931392Notes

Reaction equation

HRID 1931392 reaction equation
Br[C:2]1[S:6][C:5]([CH:7]=[CH:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:2]1[S:6][C:5]([CH:7]=[CH:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343542-Fluorophenylboronic acidHCID 35655923-(5-Bromo-2-thienyl)-2-propenoic acid

Product 1

HCID 53412006HCID 53412006, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

9.38 g (40.2 mmol) of 3-(5-bromo-thiophen-2-yl)-acrylic acid and 6.97 g (6 mmol) of tetrakis(triphenylphosphine)palladium were dissolved in 50 ml of degassed DME and stirred at room temperature for 10 min. 8.44 g (60.4 mmol) of 2-fluoro -phenylboronic acid and 50 ml of a 2 M aqueous sodium carbonate solution were added together with an additional 5 ml of degassed DME. The reaction mixture was heated to 95° C. for 4 h and then stirred at room temperature for 16 h. The product precipitated partially from the reaction mixture and was collected by filtration. This solid was boiled for 1 h in ethyl acetate and filtered while hot. The solvent was removed under reduced pressure. The filtrate of the reaction mixture was evaporated to dryness. This residue was taken up in ethyl acetate/water and filtered. The organic phase was dried with sodium sulfate, filtered, and the solvent was evaporated. The combined product was purified by silica gel chromatography. Yield: 7.5 g.

Workup

  1. temperatureThe reaction mixture was heated to 95° C. for 4 h
  2. stirringstirred at room temperature for 16 h
  3. customThe product precipitated partially from the reaction mixture
  4. filtrationwas collected by filtration
  5. waitThis solid was boiled for 1 h in ethyl acetate
  6. filtrationfiltered while hot
  7. customThe solvent was removed under reduced pressure
  8. customThe filtrate of the reaction mixture was evaporated to dryness
  9. filtrationfiltered
  10. dry with materialThe organic phase was dried with sodium sulfate
  11. filtrationfiltered
  12. customthe solvent was evaporated
  13. customThe combined product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-7a7c47cdc15942f9bec7721734b721c7
Source dataset
uspto-grants-2012_05
Patent number
US08188291B2

Reaction notes

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