3-Methoxyaniline → HCID 57825031, compound

Participants

Reaction Conditions

Reaction Steps

A microwave tube was charged with 4-(3-bromo-phenyl)-4-(4-ethoxy-3-methyl-phenyl)-4,5-dihydro-oxazol-2-ylamine (Building Block M, 175 mg, 0.467 mmol, 1.0 eq), sodium tert-butoxide (89 mg, 0.933 mmol, 2.0 eq.), 2-di-t-butylphosphino-2′,4′,6′-tri-1-propyl-1,1′biphenyl (18 mg, 0.042 mmol, 0.042 eq.), tris(dibenzylideneacetone)dipalladium (10 mg, 0.012 mmol, 0.025 eq.) and 3-methoxyaniline (115 mg, 0.933 mmol, 2.0 eq.). After three vacuum-nitrogen cycles, toluene was introduced (1 mL), the tube was scaled and stirred at 100° C. for 16 hours. After cooling to room temperature, water (1 mL) and ethylacetate (1 mL) were added. The organic fraction of the reaction mixture was placed on an SCX column. This was then washed with dichloromethane/methanol. The desired product was obtained by eluting with 2 M ammonia in methanol. Fractions containing the compound were combined and the product purified further using preparative HPLC to yield 95 mg (30% yield) of the title compound as a white solid.

Provenance & Evidence