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Cesium fluoride → 6-Chloro-4'-fluoro-4-(pyridazin-4-yl)biphenyl-3-ol

HRID 1619703
ノート
印刷プレビュー

反応式

HRID 1619703 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 25953Cesium fluorideHCID 64097334-(Tributylstannyl)pyridazineHCID 580423526-Chloro-4'-fluoro-4-iodobiphenyl-3-ol

生成物 1

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

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒
HCID 9811564
Bis(dibenzylideneacetone)palladium
触媒
HCID 6342Acetonitrile溶媒

反応条件

温度
45 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9ee11bb48fe04983a7c803ad7b46bea2
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08772293B2

反応ノート

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