4-(Tri-n-butylstannyl)pyridine → 7-Chloro-2-pyridin-4-ylthieno[3,2-b]pyridine

Participants

Reaction Steps

Tereakis(triphenylphosphine)palladium (54 mg, 0.05 mmole) was added to a solution of 4-(tributylstannyl)pyridine (0.432 g, 1.17 mmole) and 7-chloro-2-iodothieno[3,2-b]pyridine (0.347 g, 1.17 mmole) in DMF (5 ml). The reaction mixture was stirred at reflux for 3h, cooled to room temperature. The mixture was filtered, washed with CH2Cl2 and was partitioned between H2O (50 ml) and CH2Cl2 (2×50 ml). The combined organic layers were dried over MgSO4 and concentrated. The residue was purified by flash column chromatography eluting with 30–60% EtOAc in hexane to give pale yellow color solid (0.103 g, 36%); 1H NMR (300 MHz, CDCl3) δ 8.61 (1H, d, J=5.1 Hz), 7.95 (1H, s), 7.66 (2H, m), 7.44 (2H, m), 7.31 (1H, d, J=5.1 Hz); ESIMS (MH+): 481.10.

Provenance & Evidence