5-bromo-1,2-dimethyl-1H-imidazole → 5-[(4-Chlorophenyl)carbonyl]-1,2-dimethyl-1H-imidazole

HRID 627495Notes

Reaction equation

HRID 627495 reaction equation
Br[C:2]1[N:6]([CH3:7])[C:5]([CH3:8])=[N:4][CH:3]=1.C([Mg]Cl)(C)C.[Cl:14][C:15]1[CH:26]=[CH:25][C:18]([C:19](N(OC)C)=[O:20])=[CH:17][CH:16]=1>C1COCC1>[Cl:14][C:15]1[CH:26]=[CH:25][C:18]([C:19]([C:2]2[N:6]([CH3:7])[C:5]([CH3:8])=[N:4][CH:3]=2)=[O:20])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 72048795-bromo-1,2-dimethyl-1H-imidazoleHCID 112756634-Chloro-N-methoxy-N-methylbenzamideHCID 178418918HCID 178418918, compound

Product 1

HCID 867160735-[(4-Chlorophenyl)carbonyl]-1,2-dimethyl-1H-imidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a 50-mL round-bottom flask containing a solution of 5-bromo-1,2-dimethyl-1H-imidazole (440 mg, 2.51 mmol, Intermediate 24, step a) and THF (20 mL) under nitrogen was added isopropylmagnesium chloride in THF (2.0 M, 1.2 mL, 2.4 mmol) dropwise. The mixture was stirred for 0.5 hours at room temperature, and a solution of 4-chloro-N-methoxy-N-methylbenzamide (500 mg, 2.50 mmol, Intermediate 18, step a) in THF (5 mL) was introduced. After stirring for 7.5 hours at room temperature, the reaction was quenched by addition of 10 mL of EtOH, and concentrated under vacuum. The residue was purified by flash column chromatography (silica gel, 50% EtOAc in petroleum, 0-10% MeOH in CH2Cl2) to give the title compound as a white solid.

Workup

  1. stirringAfter stirring for 7.5 hours at room temperature
  2. customthe reaction was quenched by addition of 10 mL of EtOH
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by flash column chromatography (silica gel, 50% EtOAc in petroleum, 0-10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-2fc5d7a661ef4816bcdeedcc3c904182
Source dataset
uspto-grants-2016_04
Patent number
US09309222B2

Reaction notes

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