2-(Tributylstannyl)pyridine → HCID 66611387, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(5-chloro-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (0.100 g, 0.171 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (4.08 mg, 8.56 μmol), tris(dibenzylideneacetone)dipalladium(0) (7.84 mg, 8.56 μmol) and 2-(tributylstannyl)pyridine (0.082 g, 0.223 mmol) (Alfa Aesar) was purged with argon and toluene (0.9 mL) was added. The tube was sealed and the mixture was heated at 110° C. The reaction mixture was cooled to room temperature, treated with water, extracted with DCM (2×15 mL), dried over MgSO4, filtered and concentrated. The crude material was purified by flash chromatography using an ISCO Combiflash Companion (12 g column, 20-50% EtOAc in hexanes over 30 min; product eluted with about 30-35% EtOAc). 1H NMR (400 MHz, CDCl3) δ 11.82 (s, 1H); 9.41 (d, J=2.5 Hz, 1H); 8.93 (d, J=2.3 Hz, 1H); 8.66 (d, J=4.9 Hz, 1H); 8.30 (d, J=2.7 Hz, 1H); 7.93 (dd, J=8.9, 2.6 Hz, 1H); 7.67-7.75 (m, 1H); 7.59-7.65 (m, 1H); 7.15-7.24 (m, 5H); 6.85 (dd, J=20.0, 8.6 Hz, 4H); 6.72 (d, J=8.8 Hz, 1H); 4.87 (d, J=17.2 Hz, 4H); 3.94 (s, 3H); 3.81 (s, 3H); 3.76 (s, 3H); 2.59 (s, 3H). m/z (ESI, +ve ion) 627.0 (M+H)+.

Provenance & Evidence