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3-Aminobiphenyl → 5-(benzyloxy)-1-biphenyl-3-yl-2-methylpyridin-4(1H)-one

HRID 571067
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HRID 571067 반응식
[CH2:1]([O:8][C:9]1[C:10](=[O:16])[CH:11]=[C:12]([CH3:15])O[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:17][C:18]1[CH:19]=[C:20]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:21]=[CH:22][CH:23]=1>CC(O)=O>[CH2:1]([O:8][C:9]1[C:10](=[O:16])[CH:11]=[C:12]([CH3:15])[N:17]([C:18]2[CH:19]=[C:20]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:21]=[CH:22][CH:23]=2)[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
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참가 물질

4

반응물 2

HCID 167173-AminobiphenylHCID 53141715-(Benzyloxy)-2-methyl-4H-pyran-4-one

생성물 1

HCID 674193565-(benzyloxy)-1-biphenyl-3-yl-2-methylpyridin-4(1H)-one

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
160 °C

실험 절차

To a suspension of 6.6 g (30.5 mmol) 5-(benzyloxy)-2-methyl-4H-pyran-4-one in 150 ml 30% AcOH was added 7.5 g (45.8 mmol) m-aminobiphenyl. The reaction mixture was heated at 160° C. for 18 h, then cooled to rt, extracted with 300 ml EtOAc, washed with brine, and concentrated in vacuo. Purification by flash chromatography (330 g silica gel, 0-20% MeOH:EtOAc) afforded 5-(benzyloxy)-1-biphenyl-3-yl-2-methylpyridin-4(1H)-one. LCMS (M+H)+=368.3.

후처리

  1. temperaturecooled to rt
  2. extractionextracted with 300 ml EtOAc
  3. washwashed with brine
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography (330 g silica gel, 0-20% MeOH:EtOAc)

출처 및 근거

ORD 기록
ord-602a4978c21a4bcf92719a8df11007d8
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09024032B2

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