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

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).

1. customTo a two dram vial equipped with a stir bar
2. customThe vial was sealed with a septum screwcap
3. customwas placed in a 60° C.
4. temperatureheating block
5. customThe reaction solution was transfered to a 125 mL reparatory funnel
6. washThe solution was washed with water
7. dry with materialThe organic solution was dried over MgSO4
8. filtrationfiltered
9. concentrationthen concentrated in vacuo

ORD record

ord-904ecb68d05c4122b770ad54275b3222

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09334279B2