Toluene → 6'-(Dimethylamino)-N-((2'-fluoro-2,4'-bipyridin-5-yl)methyl)-3,3'-bipyridine-6-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a tube was added 5-bromo-N-((2′-fluoro-2,4′-bipyridin-5-yl)methyl)picolinamide 38-4 (38 mg, 0.10 mmol), 6-(dimethylamino)pyridin-3-ylboronic acid 38-5 (33 mg, 0.20 mmol), Pd(PPh3)4 (11 mg, 0.01 mmol), toluene (0.4 mL), ethanol (0.1 mL) and 2M Na2CO3 (0.15 mL). The reaction mixture was bubbled with nitrogen for 2 minutes and stirred at 90° C. for 10 hours with the tube sealed. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (100 mL) and washed with saturated NaHCO3 aqueous solution, H2O and brine. The organic phase was dried over Na2SO4 and concentrated to dryness by rotary evaporation. The crude product was purified with reverse phase HPLC to give 6′-(dimethylamino)-N-((2′-fluoro-2,4′-bipyridin-5-yl)methyl)-3,3′-bipyridine-6-carboxamide 38 as a white powder. MS m/z 429.20 (M+1); 1H NMR 400 MHz (DMSO-d6) δ 9.52 (t, 1H, J=6.4 Hz), 8.94 (d, 1H, J=2.4 Hz), 8.73 (d, 1H, J=2.0 Hz), 8.60 (d, 1H, J=2.4 Hz), 8.35 (d, 1H, J=5.2 Hz), 8.22 (m, 1H), 8.15 (d, 1H, J=8.0 Hz), 8.06-7.93 (m, 4H), 7.80 (s, 1H), 6.78 (d, 1H, J=9.2 Hz), 4.60 (d, 2H, J=6.4 Hz), 3.09 (s, 6H).

Provenance & Evidence