Methyl iodide → 2-(5-Bromo-2-fluoro-phenyl)-1-methyl-1H-benzoimidazole

HRID 2047389Notes

Reaction equation

HRID 2047389 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]([F:19])=[C:8]([C:10]2[NH:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[N:11]=2)[CH:9]=1.[CH3:20]I>C1COCC1>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([F:19])=[C:8]([C:10]2[N:11]([CH3:20])[C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 432364512-(5-Bromo-2-fluoro-phenyl)-1H-benzoimidazole

Product 1

HCID 595681902-(5-Bromo-2-fluoro-phenyl)-1-methyl-1H-benzoimidazoleYield 97.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH 60% suspension in mineral oil (0.61 g, 25.5 mmol) was added to a solution of 2-(5-Bromo-2-fluoro-phenyl)-1H-benzoimidazole (3.70 g, 12.76 mmol) in dry THF (100 mL) and the reaction was stirred at room temperature 30 minutes before adding methyl iodide (1.19 mL, 19.1 mmol). Reaction was left stirring for 2 h, then quenched with water (20 mL) The solution was concentrated, then AcOEt (30 mL) was added. The organic solution was separated, washed with brine (10 mL), dried over Na2SO4 and concentrated under reduced pressure to afford 3.80 g of desired compound. (97%).

Workup

  1. customReaction
  2. waitwas left
  3. stirringstirring for 2 h
  4. customquenched with water (20 mL) The solution
  5. concentrationwas concentrated
  6. additionAcOEt (30 mL) was added
  7. customThe organic solution was separated
  8. washwashed with brine (10 mL)
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9f0c9c3d6d3a4d3a8e3db4727118e70f
Source dataset
uspto-grants-2013_11
Patent number
US08592463B2

Reaction notes

Loading…