Sodium Carbonate → 2-(5-methyl-2-pyridyl)thiophene

Participants

Reaction Steps

A mixture of 2-thiopheneboronic acid (0.483 g, 3.78 mmol), 2-bromo-5-methylpyridine (0.5 g, 2.91 mmol), a solution of Na2CO3 (1M in H2O, 7.8 mL, 7.8 mmol) and a catalytic amount of Pd(PPh3)4 in DME (10 mL) was heated at the reflux temperature for 3 h., then allowed to cool to room temperature and poured onto ice. The resulting mixture was stirred for 10 min and extracted with CH2Cl2 (2×25 mL), dried (MgSO4) and concentrated under reduced pressure. The crude product was purified by flash chromatography (70% EtOAc/hex) to give 2-(5-methyl-2-pyridyl)thiophene (0.499 g, 98%): GC-MS m/z (rel abundance) 176 (MH+, 100%); 1H NMR (CDCl3) δ 1.39 (s, 3H), 7.15 (m, 1H), 7.39 (m, 1H), 7.61-7.43 (m, 3H), 8.41 (s, 1H).

Provenance & Evidence