Sodium Carbonate → Methyl 4-(1-methyl-4-oxo-1,4-dihydropyridin-3-yl)benzoate

HRID 910607Notes

Reaction equation

Br.Br[C:3]1[C:8](=[O:9])[CH:7]=[CH:6][N:5]([CH3:10])[CH:4]=1.[CH3:11][O:12][C:13]([C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)=[O:14].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.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>[CH3:10][N:5]1[CH:6]=[CH:7][C:8](=[O:9])[C:3]([C:18]2[CH:19]=[CH:20][C:15]([C:13]([O:12][CH3:11])=[O:14])=[CH:16][CH:17]=2)=[CH:4]1

Participants

Conditions

Temperature: 100 °C

Procedure

3-Bromo-1-methylpyridin-4(1H)-one hydrobromide (640 mg) was suspended in toluene (10 ml) and water (5 ml), and [4-(methoxycarbonyl)phenyl]boronic acid (642 mg), sodium carbonate (757 mg) and tetrakis(triphenylphosphine)palladium(0) (138 mg) were added, followed by stirring under heating in an oil bath at 100° C. for 3 hours. The reaction mixture was filtered through Celite, followed by extraction with ethyl acetate. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL Ltd., the same shall apply hereinunder) (chloroform:methanol=90:10) to obtain methyl 4-(1-methyl-4-oxo-1,4-dihydropyridin-3-yl)benzoate (118 mg).

Workup

filtrationThe reaction mixture was filtered through Celite
extractionfollowed by extraction with ethyl acetate
concentrationThe organic layer was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL Ltd

Sources & evidence

ORD record: ord-d8dadfb36d564b3787e009425b8e300a
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022208B2

Reaction notes

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