6-Bromo-2,3'-bipyridine → 6-[7-([1,2,4]Triazol-1-ylmethyl)imidazo[1,2-alpha]pyrimidin-3-yl]-2,3'-bipyridine

Participants

Reaction Steps

To the degassed solution of 7-([1,2,4]triazol-1-ylmethyl)-3-tributylstannylimidazo[1,2-α]pyrimidine was added 6-bromo-2,3′-bipyridine (prepared according to Example 49) (0.39 g, 1.65 mmol) and tetrakis(triphenylphosphine)palladium(0) (173 mg, 0.10 mmol) and the mixture heated at reflux for 3 h. The crude reaction was adsorbed onto silica and purified by chromatography on silica gel eluting with a dichloromethane, methanol, aqueous ammonia (33%) mixture in the volume ratios of 90:5:0.5 respectively to give 6-[7-([1,2,4]triazol-1-ylmethyl)imidazo[1,2-α]pyrimidin-3-yl]-2,3′-bipyridine as a hygroscopic solid following crystallisation from dichloromethane/ethyl acetate. Addition of an excess of 1M HCl in ether to a solution of the product in a methanol/ether solvent mixture gave 50 mg of the dihydrochloride salt as a white solid: δH (360 MHz, CDCl3) 5.62 (2H, s), 6.96 (1H, d, J 7), 7.47 (1H, dd, J 4.7 and 4.7), 7.66 (1H, d, J 7.7), 7.78 (1H, d, J 7.9), 7.91 (1H, t, J 9), 8.05 (1H, s), 8.23-8.27 (1H, m), 8.36 (1H, s), 8.41 (1H, s), 8.71-8.72 (1H, m), 9.25 (1H, s), 10.30 (1H, d, J 7.2); m/z (ES+) 355 (M++H).

Provenance & Evidence