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

HRID 1517588Notes

Reaction equation

HRID 1517588 reaction equation
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

Participants

6

Reactant 4

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

Product 1

HCID 573298662-Bromo-3-imidazol-1-ylmethyl-pyridineYield 63.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
50 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-d9cee86c61e94633b4a49e1d78eea4d2
Source dataset
uspto-grants-2012_07
Patent number
US08232289B2

Reaction notes

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