Nitrogen → N-tert-Butyl-3-methylpyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

To a 3 or 4-necked flask (100 L) with water cooling condenser, mechanical stirring and N2 was charged toluene (40 L), 2-bromo-3-methylpyridine (4.966 kg), sodium t-butoxide (5.60 kg). The slurry was then sparged N2 for 10 min; then tris(dibenzylideneacetone)dipalladium (0) (Pd2(dba)3, 0.065 kg, 0.071 mol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (BINAP, 0.106 kg, 0.171 mol) and t-butylamine (4.51 L) were charged. The resulting dark mixture was stirred 10 min at 23° C. under N2 and then heated to 70° C. (internal temp) with a steam bath. No t-butyl amine reflux was noticed.

Provenance & Evidence