Dichloromethane → 6-Bromo-4-fluoro-2-methyl-1-(propan-2-yl)-1H-benzimidazole

HRID 2264365Notes

Reaction equation

HRID 2264365 reaction equation
CC(C)([O-])C.[K+].[Br:7][C:8]1[CH:13]=[C:12]([F:14])[C:11]([NH:15][C:16](=[N:18][CH:19]([CH3:21])[CH3:20])[CH3:17])=[C:10](F)[CH:9]=1.C(Cl)Cl>CNC=O>[Br:7][C:8]1[CH:13]=[C:12]([F:14])[C:11]2[N:15]=[C:16]([CH3:17])[N:18]([CH:19]([CH3:21])[CH3:20])[C:10]=2[CH:9]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 23665647Potassium tert-butoxideHCID 674267372177297-18-4

Product 1

HCID 569716626-Bromo-4-fluoro-2-methyl-1-(propan-2-yl)-1H-benzimidazoleYield 99.9%

Reagents, catalysts & solvents 1

HCID 31254N-MethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Add potassium tert-butoxide (811.43 mg) to a solution of N-(4-bromo-2,6-difluoro-phenyl)-N′-isopropyl-acetamidine (2 g) in N-methyl formamide (20 mL). Heat the mixture at 100° C. for 2 h. Cool to RT, add DCM (150 mL), wash three times with saturated sodium chloride aqueous (brine, 300 mL), dry over magnesium sulfate and remove the solvent under vacuum. Add hexane and shake over ultrasound for a few minutes. Filter the solid, repeat addition of hexane/filtration twice to afford 1.86 g of the title compound. MS (ES+): m/z=272 (M+H)+.

Workup

  1. temperatureCool to RT
  2. washwash three times with saturated sodium chloride aqueous (brine, 300 mL)
  3. dry with materialdry over magnesium sulfate
  4. customremove the solvent under vacuum
  5. waitAdd hexane and shake over ultrasound for a few minutes
  6. filtrationFilter
  7. additionthe solid, repeat addition of hexane/filtration twice

Sources & evidence

ORD record
ord-cffe6cc889d049519a2e451df49bac50
Source dataset
uspto-grants-2010_12
Patent number
US07855211B2

Reaction notes

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