Potassium Carbonate → HCID 90015018, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2,6-dichloro-4-iodo-pyridine (1.0 g, 3.7 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydro-2H-pyridine-1-carboxylate (1.4 g; 4.4 mmol), potassium carbonate (1.0 g, 7.3 mmol), and Pd(dppf)Cl2 DCM (300 mg, 0.37 mmol) in 1,4-dioxane (12.0 mL) and water (3.0 mL) was capped in a large CEM microwave vial, de-gassed with N2, and heated in an oil-bath at 90° C. for overnight. It was diluted with water (100 mL), extracted with EtOAc (2×100 mL). The combined EtOAc was washed with brine, dried over MgSO4, filtered, and concentrated onto Celite. It was purified by column chromatography (ISCO0, 40 g column, eluded with 0-15% EtOAc/Heptane to give 670 mg (56%) of the title compound as a light yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.21 (s, 2H), 6.32 (s, 1H), 4.12 (d, J=2.7 Hz, 2H), 3.63 (t, J=5.6 Hz, 2H), 2.45 (s, 2H), 1.49 (s, 9H). LC-MS: m/z=330 (M+H+).

Provenance & Evidence