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

HRID 910607
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HRID 910607 반응식
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
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참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매
HCID 962Water용매
HCID 1140Toluene용매

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온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d8dadfb36d564b3787e009425b8e300a
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08022208B2

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