Potassium Carbonate → HCID 57706728, compound

HRID 1662544Notes

Reaction equation

HRID 1662544 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][C:11]=1OS(C(F)(F)F)(=O)=O.[CH3:28][C:29]([CH3:34])=[CH:30]B(O)O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cl-].[Na+].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:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][C:11]=1[CH:28]=[C:29]([CH3:34])[CH3:30]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27632992,2-Dimethylethenylboronic acidHCID 57706877HCID 57706877, compound

Product 1

HCID 57706728HCID 57706728, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of 83.26C (0.500 g, 1.2 mmol) in DMF (6.1 mL) at 23° C. was added 2-methylprop-1-enylboronic acid (0.24 g, 2.4 mmol, commercially available from Synthonix), and potassium carbonate (0.51 g, 3.7 mmol). Tetrakis(triphenylphosphine)palladium (0.071 g, 0.061 mmol) was then added to the mixture. The mixture was heated to 90° C. and stirred for 15 hours. The reaction was then cooled to room temperature, diluted with brine and extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was then purified on silica gel (0-10% EtOAc in hexanes) to yield 83.26D as a colorless oil (0.280 g, 73% yield).

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. extractionextracted three times with EtOAc
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. filtrationfiltering
  5. customthe organic solvent was removed under reduced pressure
  6. customthe product was then purified on silica gel (0-10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-bca531d6eabf40b29ec7a4da0071005a
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

Loading…