Sodium Carbonate → HCID 66777760, compound

HRID 2091388Notes

Reaction equation

HRID 2091388 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10](=[O:14])[CH:11]([CH3:13])[CH3:12])=[C:7]([CH3:15])[C:6]=2[CH:16]=1.[CH:17]1(B(O)O)[CH2:19][CH2:18]1.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:17]1([C:2]2[CH:3]=[CH:4][C:5]3[O:9][C:8]([C:10](=[O:14])[CH:11]([CH3:13])[CH3:12])=[C:7]([CH3:15])[C:6]=3[CH:16]=2)[CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 2760897Cyclopropylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 290760271-(5-Bromo-3-methyl-1-benzofuran-2-yl)-2-methylpropan-1-one

Product 1

HCID 66777760HCID 66777760, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

To a solution (20 mL) of 1-(5-bromo-3-methyl-1-benzofuran-2-yl)-2-methylpropan-1-one (1.0 g) synthesized in Example A182(1) in toluene were added cyclopropaneboronic acid (0.92 g), 2N aqueous sodium carbonate solution (5.3 mL), and the mixture was stirred at room temperature for 10 min under argon atmosphere. To the reaction mixture were added 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.18 g) and tris(dibenzylideneacetone)dipalladium (0) (0.10 g), and the mixture was heated under reflux under argon atmosphere overnight. The reaction mixture was cooled to room temperature, and filtered through celite, and the residue was washed with diethyl ether. Water was added to the filtrate, and the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10, volume ratio) to give the title object compound (0.80 g, 93%) as a yellow oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux under argon atmosphere overnight
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationfiltered through celite
  5. washthe residue was washed with diethyl ether
  6. additionWater was added to the filtrate
  7. concentrationthe organic layer was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10, volume ratio)

Sources & evidence

ORD record
ord-c5775248c8324daf8ba322e73b5aa8bc
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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