Dimethylformamide → HCID 86716087, compound

Participants

Reaction Conditions

Reaction Steps

A yellow solution of 6-bromo-2,4-dichloro-8-fluoro-3-phenylquinoline (1.01 g, 2.72 mmol, Intermediate 46, step a) in THF (10 mL) was stirred at −72° C. while n-BuLi (1.15 mL, 2.59 M in hexane, 2.99 mmol) was added dropwise under argon. The resulting homogeneous dark solution was stirred at −72° C. for 20 min, and was then treated with DMF (0.273 mL, 3.53 mmol) dropwise. The homogeneous dark reaction was stirred at −72° C. for 25 min, and was then removed from the cold bath and stirred under ambient conditions for 30 min. The dark homogeneous solution was quenched with 5 M NH4Cl (10 mL) and the aqueous layer was extracted with EtOAc (3×8 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated, and the residue was flash chromatographed with a 20% DCM/heptane to 100% DCM gradient to provide the title compound as a yellow powder.

Provenance & Evidence