Sodium Carbonate → HCID 53412006, compound

HRID 1873758Notes

Reaction equation

HRID 1873758 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 for 10 min at room temperature. 8.44 g (60.4 mmol) of 2-fluorophenylboronic 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 solution 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 remaining reaction solution was evaporated to dryness. The residue was taken up in ethyl acetate/water and filtered. The organic phase was dried with sodium sulfate, filtered and the solvent was removed under reduced pressure. 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 solution
  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 remaining reaction solution
  9. customwas evaporated to dryness
  10. filtrationfiltered
  11. dry with materialThe organic phase was dried with sodium sulfate
  12. filtrationfiltered
  13. customthe solvent was removed under reduced pressure
  14. customThe combined product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-319dd1a194564386a12eca28b5e03f2d
Source dataset
uspto-grants-2012_11
Patent number
US08304438B2

Reaction notes

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