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碳酸氢铯 → Methyl 4-acetylamino-2-tert-butyl-5-phenyl-4-benzofuran-7-carboxylate

HRID 17541
笔记
打印预览

反应方程式

HRID 17541 反应方程式
[C:1]([NH:4][C:5]1[C:10]2[CH:11]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[O:13][C:9]=2[C:8]([C:18]([O:20][CH3:21])=[O:19])=[CH:7][C:6]=1Br)(=[O:3])[CH3:2].[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(OCC)(=O)C>[C:1]([NH:4][C:5]1[CH:6]=[C:12]([C:14]([CH3:16])([CH3:17])[CH3:15])[O:13][C:9]2[C:10]=1[C:11]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[CH:7][C:8]=2[C:18]([O:20][CH3:21])=[O:19])(=[O:3])[CH3:2]
参与物反应条件实验过程后处理来源与证据反应笔记

参与物

5

反应物 3

HCID 10796碳酸氢铯HCID 66827苯硼酸HCID 68584863Methyl 4-acetylamino-5-bromo-2-tert-butyl-1-benzofuran-7-carboxylate

产物 1

HCID 68586991Methyl 4-acetylamino-2-tert-butyl-5-phenyl-4-benzofuran-7-carboxylate收率 80%

试剂、催化剂与溶剂 1

HCID 8857乙酸乙酯溶剂

反应条件

温度
100 °C

实验过程

Under nitrogen atmosphere, methyl 4-acetylamino-5-bromo-2-tert-butyl-1-benzofuran-7-carboxylate (I-252) (147 mg, 0.4 mmol), phenylboronic acid (61 mg, 0.5 mmol), aqueous 2 M cesium carbonate solution (0.5 ml, 1.0 mmol) and tetrakistriphenylphosphine palladium(0) (23 mg, 0.02 mmol) were added, followed by stirring at 100° C. for 6 hours. After cooling to room temperature, ethyl acetate was added to the reaction liquid, followed by washing with saturated sodium bicarbonate water and saturated brine and drying over anhydrous magnesium sulfate. After filtration and concentration under reduced pressure, the resulting residue was subjected to column chromatography, and the eluate with n-hexane/ethyl acetate (2:1) gave the entitled compound (117 mg, 80%) as a white solid.

后处理

  1. temperatureAfter cooling to room temperature
  2. washby washing with saturated sodium bicarbonate water and saturated brine
  3. dry with materialdrying over anhydrous magnesium sulfate
  4. filtrationAfter filtration and concentration under reduced pressure

来源与证据

ORD记录
ord-d5fcb61674db4886b73a55d6a063ad14
来源数据集
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
专利号
US07737166B2

反应笔记

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本页导航参与物反应条件实验过程后处理来源与证据反应笔记