Sodium Carbonate → HCID 66777760, compound

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.

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)

ORD record

ord-c5775248c8324daf8ba322e73b5aa8bc

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08436043B2