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Cesium carbonate → 3-(benzyloxy)-5-(biphenyl-3-yl)-6-(1-hydroxy-2-phenylethyl)-1-methylpyridin-2(1H)-one

HRID 625971
ノート
印刷プレビュー

反応式

HRID 625971 の反応式
[CH2:1]([O:8][C:9]1[C:10](=[O:26])[N:11]([CH3:25])[C:12]([CH:16]([OH:24])[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:13](Br)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27]1([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:32]=[CH:31][CH:30]=[C:29](B(O)O)[CH:28]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH2:1]([O:8][C:9]1[C:10](=[O:26])[N:11]([CH3:25])[C:12]([CH:16]([OH:24])[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:13]([C:38]2[CH:37]=[C:36]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:41]=[CH:40][CH:39]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 2734315(3-Phenylphenyl)boronic acidHCID 674201833-(benzyloxy)-5-bromo-6-(1-hydroxy-2-phenylethyl)-1-methylpyridin-2(1H)-one

生成物 1

HCID 711499563-(benzyloxy)-5-(biphenyl-3-yl)-6-(1-hydroxy-2-phenylethyl)-1-methylpyridin-2(1H)-one収率 25%

試薬・触媒・溶媒 1

HCID 178418807
HCID 178418807、化合物
触媒

実験手順

To a solution of 3-(benzyloxy)-5-bromo-6-(1-hydroxy-2-phenylethyl)-1-methylpyridin-2(1H)-one (0.34 g, 0.821 mmol) in 2 mL THY was added PdCl2(dppf)-CH2Cl2 adduct (67 mg, 0.082 mmol), biphenyl-3-ylboronic acid (179 mg, 0.903 mmol), and 1 N aqueous cesium carbonate solution (2 mL, 2 mmol). The resulting mixture was microwaved in a sealed vial at 155° C. for 10 min. The aqueous layer was removed and discarded, and the organic layer was collected, dried over anhydrous magnesium sulfate, concentrated and purified by silica gel chromatography to afford 3-(benzyloxy)-5-(biphenyl-3-yl)-6-(1-hydroxy-2-phenylethyl)-1-methylpyridin-2(1H)-one (100 mg, 0.205 mmol, 25% yield).

後処理

  1. customThe resulting mixture was microwaved in a sealed vial at 155° C. for 10 min
  2. customThe aqueous layer was removed
  3. customthe organic layer was collected
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. custompurified by silica gel chromatography

出典と根拠

ORDレコード
ord-f3a24909980e4b99a960f6b4c3cc57e5
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09309199B2

反応ノート

読み込み中…

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