Potassium Hydroxide → N-((6-(5-(But-3-enyloxy)-2,4-dimethylphenyl)pyridin-2-yl)methylene)-2,6-diisopropylaniline

HRID 2047949ノート

反応式

HRID 2047949 の反応式
Br[C:2]1[N:7]=[C:6]([CH:8]=[N:9][C:10]2[C:15]([CH:16]([CH3:18])[CH3:17])=[CH:14][CH:13]=[CH:12][C:11]=2[CH:19]([CH3:21])[CH3:20])[CH:5]=[CH:4][CH:3]=1.[CH2:22]([O:26][C:27]1[C:28]([CH3:37])=[CH:29][C:30]([CH3:36])=[C:31](B(O)O)[CH:32]=1)[CH2:23][CH:24]=[CH2:25].[OH-].[K+]>[Br-].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.[Pd+].C1COCC1>[CH2:22]([O:26][C:27]1[C:28]([CH3:37])=[CH:29][C:30]([CH3:36])=[C:31]([C:2]2[N:7]=[C:6]([CH:8]=[N:9][C:10]3[C:15]([CH:16]([CH3:18])[CH3:17])=[CH:14][CH:13]=[CH:12][C:11]=3[CH:19]([CH3:21])[CH3:20])[CH:5]=[CH:4][CH:3]=2)[CH:32]=1)[CH2:23][CH:24]=[CH2:25]

参加物

6

反応物 3

HCID 14797Potassium HydroxideHCID 594796125-(But-3-enyloxy)-2,4-dimethylphenylboronic acidHCID 59479616N-[(6-Bromo-2-pyridinyl)methylene]-2,6-bis(1-methylethyl)benzenamine

生成物 1

HCID 59479617N-((6-(5-(But-3-enyloxy)-2,4-dimethylphenyl)pyridin-2-yl)methylene)-2,6-diisopropylaniline

試薬・触媒・溶媒 2

HCID 178454878HCID 178454878、化合物触媒HCID 8028Tetrahydrofuran溶媒

実験手順

In the glovebox, N-((6-bromopyridin-2-yl)methylene)-2,6-diisopropylaniline (1.392 g, 4.03 mmol) is combined with 5-(but-3-enyloxy)-2,4-dimethylphenylboronic acid (1.000 g, 4.03 mmol) and KOH (0.678 g, 12.1 mmol) and dry THF (40 mL) is added. Palladium(I) tri-tert-butylphosphine bromide, dimer [PtBu3)PdBr]2 (0.062 g, 0.040 mmol) is added and the reaction mixture is stirred for five hours, removed from the glovebox, and ether (100 mL) is added. The solution is washed with water (50 mL) and then brine (50 mL), dried over magnesium sulfate, filtered, and solvents removed by evaporation. Yield=1.86 g of orange sticky oil. The product is used without further purification.

後処理

  1. additionis added
  2. customremoved from the glovebox, and ether (100 mL)
  3. additionis added
  4. washThe solution is washed with water (50 mL)
  5. dry with materialbrine (50 mL), dried over magnesium sulfate
  6. filtrationfiltered
  7. customsolvents removed by evaporation
  8. customThe product is used without further purification

出典と根拠

ORDレコード
ord-8a50c24fee944aaf8504f487d0ca5fe4
出典データセット
uspto-grants-2013_11
特許番号
US08592615B2

反応ノート

読み込み中…