Dimethylformamide → 3-Bromoquinoline-2-carbaldehyde

Participants

Reaction Steps

To isopropylmagnesium chloride lithium chloride complex solution (1.3M in THF; 50 mL, 65 mmol) was added 2,2,6,6-tetramethylpiperidine (11.5 mL, 68.3 mmol) dropwise, and the mixture was stirred overnight at room temperature. To 55 mL of the resulting solution at −25° C. under N2 was added 3-bromoquinoline (6.52 mL, 48 mmol) dropwise, and the reaction was stirred for 1 hour. DMF (3 mL) was added, and the reaction was slowly warmed to room temperature and monitored by analytical LCMS. The mixture was quenched with saturated aqueous NH4Cl and worked-up. The residue was purified by silica gel chromatography to give the title compound.

Provenance & Evidence