Water → HCID 11323995, compound

Participants

Reaction Steps

2-Chloro-6-(3-pyridin-2-yl-1H-pyrrol-1-yl)pyridine (256 mg, 1.0 mmol), diethyl-(3-pyridyl)borane (162 mg, 1.1 mmol), bis(triphenylphosphine)palladium dichloride (35 mg, 0.05 mmol), and potassium carbonate (345 mg, 2.5 mmol) were combined in 3 mL of 1:1 DME:H2O and heated via microwave irradiation for 5 min at 160° C. The reaction was diluted with 50 mL EtOAc and partitioned with H2O (50 mL). The EtOAc layer was dried over MgSO4, filtered, and concentrated in vacuo. The crude material was purified by SiO2 chromatography, eluting with a 20-75% EtOAc in hexanes gradient to afford 6-(3-pyridin-2-yl-1H-pyrrol-1-yl)-2,3′-bipyridine as a tan solid that was dissolved in ether and precipitated as an HCl salt by slow addition of 6 equivalents of 1N HCl in ether. H-NMR (CD3OD, 500 MHz) δ 9.82 (s, 1H), 9.48 (d, 1H), 9.14 (dd, 1H), 8.95 (d, 1H), 8.62 (d, 1H), 8.52 (dd, 1H), 8.44 (d, 1H), 8.28 (dd, 1H), 8.17-8.25 (m, 2H), 8.04 (m, 1H), 7.95 (d, 1H), 7.78 (dd, 1H), 7.15 (m, 1H). MS (ESI) 299.44 (M+H+).

Provenance & Evidence