乙醇 → Ethyl 5-(difluoromethoxy)picolinate

HRID 15045

反应方程式

HRID 15045 反应方程式
CN([CH:4]=[O:5])C.[CH2:6]([OH:8])[CH3:7].Br[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH:17]([F:19])[F:18])=[CH:12][N:11]=1.C(N(CC)CC)C>[C]=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH2:6]([O:8][C:4]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH:17]([F:19])[F:18])=[CH:12][N:11]=1)=[O:5])[CH3:7]

参与物

8

反应物 4

HCID 702乙醇HCID 6228N,N-二甲基甲酰胺HCID 8471三乙胺HCID 231205792-溴-5-二氟甲氧基-吡啶

产物 1

HCID 68430338Ethyl 5-(difluoromethoxy)picolinate收率 80%

试剂、催化剂与溶剂 3

HCID 167845palladium acetate催化剂HCID 6359561,1'-双(二苯基膦)二茂铁催化剂HCID 178418416HCID 178418416，化合物溶剂

实验过程

A DMF (15 mL)-ethanol (15 mL) mixed solvent solution of 2-bromo-5-difluoromethoxypyridine (1.32 g, 5.89 mmols), palladium acetate (132 mg, 0.59 mmol), 1,1′-bis(diphenylphosphino)ferrocene (654 mg, 1.18 mmols) and triethylamine (1.6 mL, 11.8 mmols) was stirred overnight at 50° C. in carbon monoxide atmosphere. The reaction liquid was cooled to room temperature and the solvent was concentrated under reduced pressure. Ethyl acetate was added to the resulting residue, followed by washing with water and drying over anhydrous magnesium sulfate. Concentrating the solvent under reduced pressure, the residue was purified on silica gel column chromatography (C-300, hexane:ethyl acetate=4:1-3:2) to provide the title compound (1.03 g, 80%).

后处理

  1. customThe reaction liquid
  2. concentrationthe solvent was concentrated under reduced pressure
  3. additionEthyl acetate was added to the resulting residue
  4. washby washing with water
  5. dry with materialdrying over anhydrous magnesium sulfate
  6. concentrationConcentrating the solvent under reduced pressure
  7. customthe residue was purified on silica gel column chromatography (C-300, hexane:ethyl acetate=4:1-3:2)

来源与证据

ORD记录
ord-c61847675b0b4ea78310640084b42d11
来源数据集
uspto-grants-2010_06
专利号
US07732456B2

关联笔记

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