Sodium bis(trimethylsilyl)amide → 6-Chloro-4-[(R)-1-(5-fluoro-2-methoxy-phenyl)-ethoxy]-pyridazin-3-ylamine

Participants

Reaction Conditions

Reaction Steps

To a solution of (R)-1-(5-fluoro-2-methoxy-phenyl)-ethanol (4.78 g, 28 mmol, 1.5 eq.) in tetrahydrofuran (40 mL) was added 2-amino-4-bromo-6-chloro-pyridazine (3.9 g, 18.7 mmol) followed by a solution of sodium hexamethyldisilazide (1M in tetrahydrofuran, 28.1 mL, 1.5 eq.). This mixture was then heated to 66° C. for 18 hr before cooling and evaporating under reduced pressure. The residue was purified by chromatography on silica gel (150 g) eluting with a gradient of ethyl acetate in heptane (10:90 to 50:50) to give the title compound as a yellow solid (3.0 g, 54%).

Provenance & Evidence