Benzothiazole → 4-(Benzo[d]thiazol-2-yl(5-ethoxy-2-fluoro-3-isopropoxyphenyl)methylamino)benzonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of benzothiazole (61.9 mg, 0.458 mmol) in 2 mL THF at −78° C. was added 1.6 M solution of BuLi in THF (315 μL, 0.504 mmol). The mixture was stirred at −78° C. for 45 min, then a solution of Intermediate 7.3 (149 mg, 0.458 mmol) in 0.5 mL THF was added dropwise. The mixture was stirred and allowed to warm to rt overnight, then was quenched with sat. NH4Cl. The mixture was diluted with EtOAc, washed with H2O and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0 to 50% EtOAc/hexanes gradient) to afford 90 mg of Intermediate 7.4 as a white solid.

Provenance & Evidence