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

HRID 625971
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HRID 625971 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 178418807
HCID 178418807, 화합물
촉매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f3a24909980e4b99a960f6b4c3cc57e5
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09309199B2

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