Imidazole → 1-(4-Bromo-2-methyl-benzyl)-1H-imidazole

HRID 395190Notes

Reaction equation

[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[Br:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15]Br)=[C:11]([CH3:17])[CH:10]=1>CN(C=O)C>[Br:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[C:11]([CH3:17])[CH:10]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of imidazole (58.0 mg, 0.86 mmol) in 3 mL DMF was treated with NaH (20.0 mg, 0.86 mmol) and heated to 90° C. After 1 h a solution of 4-bromo-1-bromomethyl-2-methyl-benzene (Intermediate 138, 190.0 mg, 0.72 mmol) in 3 mL DMF was added and stirring at 90° C. continued for I hour. The solution was cooled to room temperature and concentrated under reduced pressure. The title compound, 160.0 mg (88%) was isolated by column chromatography (5% MeOH-EtOAc) as a colorless solid.

Workup

temperatureThe solution was cooled to room temperature
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-3cbc1c4e75074f479735835bbc22882f
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06603019B2

Reaction notes

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