Sodium Carbonate → HCID 86639497, compound

HRID 1854719Notes

Reaction equation

Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([N:10]([CH3:12])[CH3:11])[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:11][N:10]([CH3:12])[C:4]1[CH:3]=[C:2]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:9]=[CH:8][C:5]=1[CH:6]=[O:7]

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of 4-bromo-2-dimethylaminobenzaldehyde (250 mg, 1.10 mmol), sodium carbonate (140 mg, 1.32 mmol), and phenylboronic acid (210 mg, 1.65 mmol) in 2.2 mL of N,N-dimethylformamide/water (2:1) was added palladium acetate (13 mg, 58 μmol) under nitrogen. After being stirred at 100° C. overnight, the reaction mixture was filtered. The filtrate was diluted with ethyl acetate, and the solution was washed with saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 80/20) to obtain the title compound as a yellow oil (226 mg, 91%).

Workup

filtrationthe reaction mixture was filtered
additionThe filtrate was diluted with ethyl acetate
washthe solution was washed with saturated NaHCO3 aqueous solution, brine
dry with materialdried over MgSO4
filtrationAfter filtration
concentrationthe filtrate was concentrated in vacuo
customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 80/20)

Sources & evidence

ORD record: ord-1bc4f157239643e29eb7fca0cad197a3
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962674B2

Reaction notes

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