正丁胺 → Methyl 3-bromo-5-(butylamino)-4-methoxybenzoate

HRID 14191

反应方程式

HRID 14191 反应方程式
C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:53]([NH2:57])[CH2:54][CH2:55][CH3:56].Br[C:59]1[CH:60]=[C:61]([CH:66]=[C:67]([Br:71])[C:68]=1[O:69][CH3:70])[C:62]([O:64][CH3:65])=[O:63]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:71][C:67]1[CH:66]=[C:61]([CH:60]=[C:59]([NH:57][CH2:53][CH2:54][CH2:55][CH3:56])[C:68]=1[O:69][CH3:70])[C:62]([O:64][CH3:65])=[O:63]

参与物

7

反应物 4

HCID 8007正丁胺HCID 10796碳酸氢铯HCID 6348761,1'-联萘-2,2'-双二苯膦 (BINAP)HCID 21086155Methyl 3,5-dibromo-4-methoxybenzoate

产物 1

HCID 21086160Methyl 3-bromo-5-(butylamino)-4-methoxybenzoate

试剂、催化剂与溶剂 2

HCID 167845palladium acetate催化剂HCID 1140甲苯溶剂2 次

反应条件

温度
80 °C

实验过程

To a stirred solution of Pd(OAc)2 (144 mg), BINAP (1.2 g), and cesium carbonate (8.4 g) in toluene (100 mL) was added butylamine (1.6 mL), and the mixture was heated at 80° C. for 15 min. A solution methyl 3,5-dibromo-4-methoxybenzoate (4.2 g) in toluene (30 mL) was added dropwise over 20 min. The mixture was refluxed overnight. The mixture was cooled to room temperature, filtered through diatomaceous earth, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 1:9 ethyl acetate/hexanes) provided 3.5 g of the title compound: 1H NMR (300 MHz, CDCl3) δ 7.52, 7.19, 3.90, 3.88, 3.18, 1.66, 1.46, 0.97.

后处理

  1. temperatureThe mixture was refluxed overnight
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered through diatomaceous earth
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash column chromatography (silica, 1:9 ethyl acetate/hexanes)

来源与证据

ORD记录
ord-cb35870106e04ff18d5775ee15a2958c
来源数据集
uspto-grants-2010_06
专利号
US07727997B2

关联笔记

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