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

HRID 910607
ノート
印刷プレビュー

反応式

HRID 910607 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒
HCID 962
Water
溶媒
HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d8dadfb36d564b3787e009425b8e300a
出典データセット
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08022208B2

反応ノート

読み込み中…

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