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Carbonic acid sodium salt (1:2) → Methyl 3-[6-(4-fluorophenyl)pyridin-3-yl]prop-2-enoate

HRID 238299
笔记
打印预览

反应方程式

HRID 238299 反应方程式
[CH3:1][O:2][C:3](=[O:13])[CH:4]=[CH:5][C:6]1[CH:7]=[N:8][C:9](Br)=[CH:10][CH:11]=1.[F:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3](=[O:13])[CH:4]=[CH:5][C:6]1[CH:7]=[N:8][C:9]([C:18]2[CH:19]=[CH:20][C:15]([F:14])=[CH:16][CH:17]=2)=[CH:10][CH:11]=1
参与物实验过程后处理来源与证据反应笔记

参与物

8

反应物 4

HCID 10340Carbonic acid sodium salt (1:2)HCID 11776三苯基膦HCID 2856454-氟苯硼酸HCID 714275823-(6-Bromopyridin-3-yl)acrylic acid methyl ester

产物 1

HCID 68821839Methyl 3-[6-(4-fluorophenyl)pyridin-3-yl]prop-2-enoate

试剂、催化剂与溶剂 3

HCID 167845乙酸钯(Ⅱ)
催化剂
HCID 702乙醇溶剂
HCID 1140甲苯溶剂

实验过程

A mixture of 2980 mg (12.31 mmol) of 3-(6-bromopyridin-3-yl)acrylic acid methyl ester, 2067 mg (14.77 mmol) of 4-fluorophenylboronic acid, 138.2 mg (0.61 mmol) of palladium(II)acetate, 322.9 mg (1.23 mmol) of triphenylphosphane and 14.7 ml of a 1M sodium carbonate solution in 73 ml of toluene and 20 ml of ethanol was heated under reflux for 1.5 h. After cooling, the mixture was poured onto water and extracted with ethyl acetate. The organic phases were evaporated and residue purified by chromatography (silica gel, n-heptane/ethyl acetate 5:1). Yield: 2.4 g (76%).

后处理

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 h
  3. temperatureAfter cooling
  4. additionthe mixture was poured onto water
  5. extractionextracted with ethyl acetate
  6. customThe organic phases were evaporated
  7. customresidue purified by chromatography (silica gel, n-heptane/ethyl acetate 5:1)

来源与证据

ORD记录
ord-be80b9617cb04a7f8fb3a2c9e0a8cdd0
来源数据集
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
专利号
US08642620B2

反应笔记

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本页导航参与物实验过程后处理来源与证据反应笔记