2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl → N-(2,6-dimethyl-4-(3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)phenyl)-3,3-dimethylbutanamide

Participants

Reaction Steps

Bis(dibenzylidineacetone)palladium (4 mg, 0.069 mmol) and (2′-dicyclohexylphosphanyl-biphenyl-2-yl)-dimethylamine (7 mg, 0.015 mmol) were added to dry toluene (1 mL purged with argon) and stirred for 15 minutes under argon. Potassium tert-butoxide (36 mg, 0.32 mmol), N-(4-bromo-2,6-dimethylphenyl)-3,3-dimethylbutanamide (52 mg, 0.17 mmol) and 3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine (WO/04069162) (40 mg, 0.15 mmol) were then added and the reaction mixture was stirred at 80° C. over night. The reaction mixture was then cooled to room temperature, concentrated and purified by biotage (75% Ethyl acetate:Hexanes) to afford the desired compound as a solid. 1H NMR (DMSO-d6, 400 MHz) δ 1.05 (s, 9H), 2.11 (s, 6H), 2.17 (s, 2H), 3.08 (t, J=5.6 Hz, 2H), 3.64 (t, J=5.9 Hz, 2H), 4.48 (s, 2H), 6.76 (s, 2H), 8.08 (s, 1H), 8.75 (s, 1H), 8.90 (s, 1H).

Provenance & Evidence