Tetrahydrofuran → 2-(4-Chloro-6-(p-tolyl)pyridin-2-yl)thiazole

Participants

Reaction Steps

To a 2 dram vial equipped with a stir bar was added 2-(4,6-dichloropyridin-2-yl)thiazole (50 mg, 0.22 mmol), p-tolylboronic acid (29 mg, 0.22 mmol), Pd(dppf)Cl2 (8 mg, 11 μmol) and K3PO4 (344 mg, 1.62 mmol). The vial was capped with a septum screw-cap and then placed under N2 atmosphere. To the vial was added THF (1 mL) and water (0.5 mL). The mixture was placed in a 60° C. oil bath with stirring for 16 h. The reaction mixture was diluted with EtOAc (5 mL) and brine (1 mL). The mixture was shaken; the aq. phase was decanted away via pipet. The organic phase was dried over MgSO4; filtered; and the filtrate was concentrated in vacuo to afford a dark amber solid. This material was subjected to silica gel chromatography (hexanes:EtOAc, 100:0 to 60:40) to afford 2-(4-chloro-6-(p-tolyl)pyridin-2-yl)thiazole as a white solid (28 mg, 45%). 1H-NMR (400 MHz, CDCl3) δ 8.12 (d, J=1.8 Hz, 1H), 8.00 (d, J=8.3 Hz, 2H), 7.96 (d, J=3.3 Hz, 1H), 7.74 (d, J=1.8 Hz, 1H), 7.50 (d, J=3.3 Hz, 1H), 7.33 (d, J=8.0 Hz, 2H), 2.44 (s, 3H).

Provenance & Evidence