碳酸钾 → 5-Chloro-3-(4-(4-(trifluoromethyl)pyridin-2-yloxy)phenyl)pyridin-2-amine

HRID 1405723笔记

反应方程式

HRID 1405723 反应方程式
C(=O)([O-])[O-].[K+].[K+].F[C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][N:9]=1.[NH2:18][C:19]1[C:24]([C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)=[CH:23][C:22]([Cl:32])=[CH:21][N:20]=1>CS(C)=O>[Cl:32][C:22]1[CH:23]=[C:24]([C:25]2[CH:26]=[CH:27][C:28]([O:31][C:8]3[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][N:9]=3)=[CH:29][CH:30]=2)[C:19]([NH2:18])=[N:20][CH:21]=1

参与物

5

反应物 3

HCID 11430碳酸钾HCID 111595142-氟-4-三氟甲基吡啶HCID 667480044-(2-Amino-5-chloropyridin-3-yl)phenol

产物 1

HCID 667479225-Chloro-3-(4-(4-(trifluoromethyl)pyridin-2-yloxy)phenyl)pyridin-2-amine收率 97.3%

试剂、催化剂与溶剂 1

HCID 679二甲基亚砜溶剂

反应条件

温度
120 °C

实验过程

A mixture of potassium carbonate (376 mg), 2-fluoro-4-(trifluoromethyl)pyridine (269 mg) and 4-(2-amino-5-chloropyridin-3-yl)phenol (300 mg) in DMSO (5 mL) was stirred at 120° C. for 2 hr. The mixture was neutralized with sat.NaHCO3 aq. and extracted with EtOAc. The organic layer was separated, washed with 1N NaOH aq. and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with EtOAc in hexane) to give the title compound (484 mg) as a pale yellow solid.

后处理

  1. extractionNaHCO3 aq. and extracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed with 1N NaOH aq. and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (NH silica gel, eluted with EtOAc in hexane)

来源与证据

ORD记录
ord-d0dbf98b303e4de9976d074db47e5fed
来源数据集
uspto-grants-2014_12
专利号
US08916551B2

反应笔记

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