5-[4-(benzyloxy)biphenyl-3-yl]-1-methyl-1H-pyrazole → 3-(1-methyl-1H-pyrazol-5-yl)biphenyl-4-ol

HRID 1619708笔记

反应方程式

HRID 1619708 反应方程式
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][C:10]=1[C:21]1[N:25]([CH3:26])[N:24]=[CH:23][CH:22]=1)C1C=CC=CC=1>CO.[Pd]>[CH3:26][N:25]1[C:21]([C:10]2[CH:11]=[C:12]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:13]=[CH:14][C:9]=2[OH:8])=[CH:22][CH:23]=[N:24]1

参与物

4

反应物 1

HCID 580422625-[4-(benzyloxy)biphenyl-3-yl]-1-methyl-1H-pyrazole

产物 1

HCID 1362008913-(1-methyl-1H-pyrazol-5-yl)biphenyl-4-ol收率 88.4%

试剂、催化剂与溶剂 2

HCID 23938钯碳催化剂HCID 887Methanol溶剂

实验过程

To a stirred suspension of 5-[4-(benzyloxy)biphenyl-3-yl]-1-methyl-1H-pyrazole (Preparation 108, 3 g, 8.81 mmol) in methanol (26 mL) was added palladium on carbon (300 mg). The mixture was stirred at room temperature under a hydrogen atmosphere for 16 hours before filtering through a Celite™ pad. The pad was washed with tetrahydrofuran and the filtrate was evaporated in vacuo. The residue was dissolved in ethyl acetate (26 mL) and the solution degassed with argon. Palladium on carbon (300 mg) was added and the mixture was stirred at room temperature under a hydrogen atmosphere for 6 hours. The catalyst was filtered off through a Celite pad and the filtrate was evaporated in vacuo. Trituration of the residue with n-hexane afforded the title compound (1.95 g) as a white solid.

后处理

  1. filtrationbefore filtering through a Celite™ pad
  2. washThe pad was washed with tetrahydrofuran
  3. customthe filtrate was evaporated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate (26 mL)
  5. customthe solution degassed with argon
  6. additionPalladium on carbon (300 mg) was added
  7. stirringthe mixture was stirred at room temperature under a hydrogen atmosphere for 6 hours
  8. filtrationThe catalyst was filtered off through a Celite pad
  9. customthe filtrate was evaporated in vacuo

来源与证据

ORD记录
ord-5e80dcb6530948e78fbed731d703b006
来源数据集
uspto-grants-2014_07
专利号
US08772293B2

反应笔记

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