Imidazole → 2-Bromo-3-imidazol-1-ylmethyl-pyridine

HRID 1517588ノート

反応式

HRID 1517588 の反応式
CS(O[CH2:6][C:7]1[C:8]([Br:13])=[N:9][CH:10]=[CH:11][CH:12]=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].[NH:20]1[CH:24]=[CH:23][N:22]=[CH:21]1.O>C(O)C>[Br:13][C:8]1[C:7]([CH2:6][N:20]2[CH:24]=[CH:23][N:22]=[CH:21]2)=[CH:12][CH:11]=[CH:10][N:9]=1

参加物

6

反応物 4

HCID 795ImidazoleHCID 962WaterHCID 11430Potassium CarbonateHCID 58268552(2-Bromo-3-pyridyl)methyl methanesulfonate

生成物 1

HCID 573298662-Bromo-3-imidazol-1-ylmethyl-pyridine収率 63.5%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

反応条件

温度
50 °C

実験手順

To a solution of (2-bromo-3-pyridyl)methyl methanesulfonate (2.5 g, 9.39 mmol) in ethanol (46.97 mL) at room temperature, potassium carbonate (2.62 g) and 1H-imidazole (1.31 g) are added. The mixture is stirred at 50° C. A thick sort of emulsion is formed and 10 mL of ethanol is added and the kind of emulsion is stirred at 50° C. overnight. Water is added until all solids are dissolved. Then, it is concentrated under reduced pressure and the residue is diluted with ethyl acetate and washed with sodium bicarbonate (saturated aqueous solution). Organic layer is decanted, dried over magnesium sulfate and solvent evaporated in vacuo. Crude material is purified by normal phase Isco chromatography using as eluent dichloromethane and methanol (98/2 to 90/10) to yield 1.42 g of the title compound. MS (m/z): 238, 240 (M+1, M+3).

後処理

  1. customA thick sort of emulsion is formed
  2. stirringthe kind of emulsion is stirred at 50° C. overnight
  3. dissolutionare dissolved
  4. concentrationThen, it is concentrated under reduced pressure
  5. additionthe residue is diluted with ethyl acetate
  6. washwashed with sodium bicarbonate (saturated aqueous solution)
  7. customOrganic layer is decanted
  8. dry with materialdried over magnesium sulfate and solvent
  9. customevaporated in vacuo
  10. customCrude material is purified by normal phase Isco chromatography

出典と根拠

ORDレコード
ord-d9cee86c61e94633b4a49e1d78eea4d2
出典データセット
uspto-grants-2012_07
特許番号
US08232289B2

反応ノート

読み込み中…