Dimethylformamide → 5-Ethyl-2-fluoro-3-morpholinobenzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of Intermediate 230.1 (102 mg, 0.487 mmol) and PMDTA (0.132 mL, 0.634 mmol) in 3 mL THF at −78° C., was added BuLi (1.6 M in THF, 0.365 mL, 0.584 mmol). The mixture was allowed to warm to −45° C. over 20 min, then was recooled to −78° C. DMF (75 μL) was added, then the reaction mixture was removed from the cooling bath and stirred 20 min before being quenched with sat. NH4Cl. The mixture was diluted with EtOAc, washed with water and brine, dried (Na2SO4) and concentrated. The crude residue was purified by flash chromatography (0 to 35% EtOAc/hexanes gradient) to afford 77 mg of Intermediate 406.1. LCMS (2 min gradient) RT=1.47 min, 238.18 (M+H)+.

Provenance & Evidence