Dimethylformamide → 4-bromo-1-trityl-1H-imidazole-2-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

To 4-bromo-1-trityl-1H-imidazole (2.00 g, 5.14 mmol) in 30 mL THF at 0° C., was added a solution of BuLi (1.6M in hexanes, 3.85 mL, 6.17 mmol). The mixture was stirred at 0° C. for 1.25 h, then DMF (0.80 mL, 10.3 mmol) was added. The mixture was stirred for 1 h at 0° C. and 1 h at rt, then was quenched with sat. NH4Cl. The mixture was diluted with EtOAc, washed with H2O and brine, dried (Na2SO4), filtered through a 1″ pad of SiO2 and concentrated. The crude product was purified by flash chromatography (0 to 40% EtOAc/hexanes gradient) to afford 1.24 g of Intermediate 175.1 as a colorless solid.

Provenance & Evidence