Tetrahydrofuran → 2-(2-Fluoropyridin-4-yl)thiazole

Participants

Reaction Steps

To a two dram vial equipped with a stir bar was added 4-bromo-2-fluoropyridine (132 mg, 0.75 mmol) and Pd(dppf)Cl2 (28 mg, 0.038 mmol). The vial was sealed with a septum screwcap and was then placed under N2 atm. To the vial was added thiazol-2-ylzinc(II) bromide in THF (3.0 mL, 1.5 mmol). The vial was placed in a 60° C. heating block with stirring for 3.5 h. The reaction solution was transfered to a 125 mL reparatory funnel and was diluted with EtOAc (50 mL). The solution was washed with water:brine (25 mL:25 mL); then brine (50 mL). The organic solution was dried over MgSO4; filtered; then concentrated in vacuo. The residue was subjected to silica gel chromatography using hexanes:EtOAc to afford 2-(2-fluoropyridin-4-yl)thiazole as a white solid, 83 mg (61%). 1H-NMR (400 MHz, CDCl3) δ 8.32 (d, J=5.3 Hz, 1H), 8.00 (d, J=3.3 Hz, 1H), 7.73 (dt, J=5.3, 1.6 Hz, 1H), 7.53 (d, J=3.3 Hz, 1H), 7.51-7.50 (m, 1H).

Provenance & Evidence