Benzophenone imine → 6-Methoxy-5-(trifluoromethyl)pyridin-3-amine

Participants

Reaction Conditions

Reaction Steps

To 5-Iodo-2-methoxy-3-(trifluoromethyl)pyridine (0.97 g, 3.20 mmol) (ECA International Product List) was added DMF (8.0 mL), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.093 g, 0.160 mmol), Pd2(dba)3 (0.147 g, 0.160 mmol), diphenylmethanimine (0.806 mL, 4.80 mmol), and sodium 2-methylpropan-2-olate (1.231 g, 12.80 mmol), and the resulting mixture was heated at 120° C. for 30 min. The reaction mixture was then diluted with 100 mL of EtOAc, added to a separatory funnel, partitioned with 1 N HCl (aqueous), and washed 2 times with 50 mL of sodium bicarbonate (saturated, aqueous). The organic layer was separated, dried over sodium sulfate, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0% to 5% (2 M ammonia in MeOH)/DCM) provided the title compound (34% yield). m/z (ESI, +ve ion) 193.2 (M+H)+.

Provenance & Evidence