5-Bromo-1-methyl-1H-imidazole → HCID 86716092, compound

Participants

Reaction Steps

A solution of 5-bromo-1-methyl-1H-imidazole (342 mg, 2.12 mmol) in DCM (2.2 mL) was stirred on an ice bath while iPrMgCl—LiCl (1.77 mL, 1.2 M in THF, 2.1 mmol) was added dropwise over 1-2 min under argon. After 10 min stirring at room temperature, the homogeneous amber reaction was added dropwise over 1-2 min to a slurry of 2,4-dichloro-8-methyl-3-phenylquinoline-6-carbaldehyde (460 mg, 1.46 mmol, Intermediate 47, step b) in LaCl3-2LiCl (7.60 mL, 0.56 M in THF, 1.46 mmol) on an ice bath. The reaction was removed from the ice bath immediately following Grignard addition and stirred for 45 min at ambient temperature, and was then partitioned with 9:1 DCM/MeOH (14 mL) and 5 M NH4Cl (0.72 mL). This was filtered over Celite®, and the filter cake washed with 9:1 DCM/MeOH (1×5 mL). The combined clear dark yellow filtrates were dried (Na2SO4), filtered, and concentrated to provide a beige foam. This was concentrated from DCM (3×15 mL) in prelude to MnO2 oxidation.

Provenance & Evidence