Sodium Carbonate → 2-fluoro-N-methyl-4-vinylbenzamide

HRID 629424Notes

Reaction equation

Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][CH3:9])=[O:7])=[C:4]([F:12])[CH:3]=1.B1(C=C)O[C:16](C)(C)[C:15](C)(C)O1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC>[F:12][C:4]1[CH:3]=[C:2]([CH:15]=[CH2:16])[CH:11]=[CH:10][C:5]=1[C:6]([NH:8][CH3:9])=[O:7]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4-bromo-2-fluoro-N-methylbenzamide (0.80 g), vinylboronic acid pinacol cyclic ester (0.80 g) and 2M aqueous sodium carbonate solution (3.45 mL) in DME (17.3 mL) was argon-purged. Bis(triphenylphosphine)palladium(II) dichloride (0.12 g) was added thereto, and the mixture was stirred overnight at 80° C. The reaction solution was diluted with ethyl acetate, and the mixture was washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to short silica gel column chromatography, and the solvent was evaporated under reduced pressure to give the title compound (0.74 g).

Workup

custompurged
additionBis(triphenylphosphine)palladium(II) dichloride (0.12 g) was added
additionThe reaction solution was diluted with ethyl acetate
washthe mixture was washed with water and saturated brine
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-2f010bc452bc4c7d8d98891fce9354b7
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315458B2

Reaction notes

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