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氟化铯 → 6-Chloro-4'-fluoro-4-(pyridazin-4-yl)biphenyl-3-ol

HRID 1619703
笔记
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反应方程式

HRID 1619703 反应方程式
[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[CH:6][C:5]([OH:15])=[C:4](I)[CH:3]=1.C([Sn](CCCC)(CCCC)[C:22]1[CH:27]=[CH:26][N:25]=[N:24][CH:23]=1)CCC.[F-].[Cs+]>C(#N)C.[Cu]I.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[CH:6][C:5]([OH:15])=[C:4]([C:22]2[CH:27]=[CH:26][N:25]=[N:24][CH:23]=2)[CH:3]=1
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

7

反应物 3

HCID 25953氟化铯HCID 64097334-TRIBUTYLSTANNYLPYRIDAZINEHCID 580423526-Chloro-4'-fluoro-4-iodobiphenyl-3-ol

产物 1

HCID 1362008786-Chloro-4'-fluoro-4-(pyridazin-4-yl)biphenyl-3-ol收率 58%

试剂、催化剂与溶剂 3

HCID 24350碘化亚铜催化剂
HCID 9811564
三(二亚苄基丙酮)二钯
催化剂
HCID 6342乙腈溶剂

反应条件

温度
45 °C

实验过程

A suspension of 6-chloro-4′-fluoro-4-iodobiphenyl-3-ol (Preparation 103, 300 mg, 0.86 mmol), 4-(tributylstannyl)-pyridazine (413 mg, 1.12 mmol), caesium fluoride (261 mg, 1.72 mmol), and copper (I) iodide (33 mg, 0.17 mmol) in acetonitrile (5 mL) was degassed for 20 minutes under nitrogen. Tetrakistriphenylphosphinepalladium (0) (100 mg, 0.09 mmol) was added and the reaction mixture was heated for 18 hours at 45° C. under nitrogen. The cooled reaction mixture was filtered through Arbocel and the Arbocel pad was washed with ethyl acetate (100 mL). The organic layer was washed with brine (2×15 mL), dried over MgSO4, filtered and evaporated. The residue was purified by silica gel chromatography eluting with 20% heptane in ethyl acetate to afford the title compound (150 mg, 58%) as an oil.

后处理

  1. customwas degassed for 20 minutes under nitrogen
  2. customThe cooled reaction mixture
  3. filtrationwas filtered through Arbocel
  4. washthe Arbocel pad was washed with ethyl acetate (100 mL)
  5. washThe organic layer was washed with brine (2×15 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by silica gel chromatography
  10. washeluting with 20% heptane in ethyl acetate

来源与证据

ORD记录
ord-9ee11bb48fe04983a7c803ad7b46bea2
来源数据集
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
专利号
US08772293B2

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