3-Aminopyridine → 4-(Pyridin-3-ylamino)picolinonitrile

Participants

Reaction Conditions

Reaction Steps

4-Chloro-2-pyridinecarbonitrile (1 g, 7 mmol, 1 eq), 3-aminopyridine (0.815 mg, 8.66 mmol, 1.20 eq), Cs2CO3 (3.29 g, 10.1 mmol, 1.40 eq), Pd2(dba)3 (332 mg, 0.577 mmol, 0.0800 eq), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (501 mg, 0.866 mmol, 0.120 eq) and dioxane (18 mL) were added to a microwave vial. The vial was purged with argon, capped and heated at 100° C. for 18 h. After cooling the reaction was filtered over a plug of celite and the plug was washed with 5% MeOH/CH2Cl2. The solvents were removed in vacuo and the crude mixture was purified by flash chromatography on silica gel afforded 1.374 g (97%) of the title compound as an orange solid: 1H NMR (400 MHz, CDCl3) δ1H NMR (400 MHz, DMSO-d6) δ 9.42 (s, 1H), 8.49 (d, J=2.6 Hz, 1H), 8.34-8.31 (m, 2H), 7.73 (dq, J=1.3, 8.2 Hz, 1H), 7.43-7.40 (m, 1H), 7.39 (d, J=2.3 Hz, 1H), 7.13 (dd, J=2.4, 5.9 Hz, 1H); ES-MS [M+1]+:197.1.

Provenance & Evidence