Nitrogen → 3-(4-Chloro-thiophen-2-yl)-pyridine

Participants

Reaction Conditions

Reaction Steps

A solution of 2-bromo-4-chloro-thiophene (Gronowitz, Rosén Chemica Scripta, 1971, 1, 33) (1.45 g, 7.34 mmol), pyridine-3-boronic acid (0.95 g, 7.71 mmol), 2 M Na2CO3 (5.50 mL, 11.01 mmol) and, n-PrOH (3 mL), is degassed with N2 for 10 minutes. Pd(OAc)2 (0.033 g, 0.15 mmol) and PPh3 (0.12 g, 0.44 mmol) are added and the solution is heated at 85° C. for 48 hours, diluted with CH2Cl2 (50 mL), washed with 10% Na2CO3 (2×30 mL), dried over MgSO4, filtered and concentrated. The residue is purified by ISCO column chromatography (20%-30% EtOAc/hexane gradient) furnish the title compound (0.74 g, 3.78 mmol, 51%). 1H NMR (CDCl3), δ 7.12-7.13 (m, 1H), 7.20 (d, J=1.4 Hz, 1H), 7.31 (dd, J=8.0, 4.9 Hz, 1H), 7.78-7.82 (m, 1H), 8.55 (d, J=4.9 Hz, 1H), 8.82 (d, J=2.2 Hz, 1H).

Provenance & Evidence