Tetrahydrofuran → 2-(4-Chloro-[2,3'-bipyridin]-6-yl)thiazole

Beteiligte Stoffe

Reaktionsschritte

To a 2 dram vial equipped with a stir bar was added 2-(4,6-dichloropyridin-2-yl)thiazole (50 mg, 0.216 mmol), 6-Methyl-2-(3-pyridinyl)-1,3,6,2-dioxazaborocane-4,8-dione (“3-Pyridineboronic acid MIDA ester”, 50.6 mg, 0.216 mmol), Pd(dppf)Cl2 (8 mg, 11 μmol) and K3PO4 (344 mg, 1.62 mmol). The vial was capped with a septum screwcap and then placed under N2 atmosphere. To the vial was added THF (1.00 mL) and water (0.20 mL). The mixture was placed in a 60° C. with stirring for 3 h. The reaction mixture was transfered to a 125 mL separatory funnel using EtOAc and water. The mixture was diluted with EtOAc (30 mL), then washed with sat. aq. NaHCO3 (20 mL). The aq. phase was extracted with EtOAc (20 mL). The combined organics were dried over MgSO4; filtered; then concentrated in vacuo to afford a solid yellow residue. This material was subjected to silica gel chromatography (hexanes:EtOAc, 100:0 to 50:50) to afford 2-(4-chloro-[2,3′-bipyridin]-6-yl)thiazole as a white solid (32 mg, 54%). 1H-NMR (400 MHz, CDCl3) δ 9.32 (dd, J=2.3, 0.8 Hz, 1H), 8.73 (dd, J=4.9, 1.6 Hz, 1H), 8.43-8.37 (m, 1H), 8.22 (d, J=1.8 Hz, 1H), 7.98 (d, J=3.0 Hz, 1H), 7.79 (d, J=1.8 Hz, 1H), 7.53 (d, J=3.3 Hz, 1H), 7.47 (ddd, J=7.9, 4.9, 1.0 Hz, 1H).

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