Tetrahydrofuran → HCID 90118173, compound

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), 6-Methyl-2-phenyl-1,3,6,2-dioxazaborocane-4,8-dione (“phenylboronic acid MIDA ester”, 50 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 screwcap 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 to afford 2-(4-chloro-6-phenylpyridin-2-yl)thiazole as a yellow solid (38 mg, 64%). 1H-NMR (400 MHz, CDCl3) δ 8.16 (d, J=1.8 Hz, 1H), 8.14-8.08 (m, 2H), 7.97 (d, J=3.0 Hz, 1H), 7.77 (d, J=1.8 Hz, 1H), 7.58-7.45 (m, 4H).

Provenance & Evidence