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

HRID 910607
Notes
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Reaction equation

HRID 910607 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343694-Methoxycarbonylphenylboronic acidHCID 673912293-Bromo-1-methylpyridin-4(1H)-one hydrobromide

Product 1

HCID 57583987Methyl 4-(1-methyl-4-oxo-1,4-dihydropyridin-3-yl)benzoateYield 20.4%

Reagents, catalysts & solvents 3

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 962WaterSolvent
HCID 1140TolueneSolvent

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

  1. filtrationThe reaction mixture was filtered through Celite
  2. extractionfollowed by extraction with ethyl acetate
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes