Cesium carbonate → HCID 22678367, compound

HRID 1837707Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:10]([O:12][CH3:13])=[O:11])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[CH3:14]OB(O)O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=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>[CH3:14][C:2]1[CH:3]=[C:4]([C:10]([O:12][CH3:13])=[O:11])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

1.2 g of methyl 5-bromo-2-methoxy-3-pyridinecarboxylate was dissolved in 20 ml of N,N-dimethylformamide, 440 mg of methylboric acid, 4.79 g of anhydrous cesium carbonate, and 564 mg of tetrakis(triphenylphosphine)palladium were added thereto, and the mixture was stirred at 120° C. for 2 hours under a nitrogen atmosphere. Ice-water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified by silica gel column chromatography (hexane:ethyl acetate=20:1), to give 461 mg of the title compound as a colorless oil.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with water and brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated
customthe crude product was purified by silica gel column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record: ord-e0e120a818734fffbf1099ba65dcd15d
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06784192B2

Reaction notes

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