反应详情

To a 2 dram vial equipped with a stir bar was added 2-(4,6-dichloropyridin-2-yl)thiazole (50 mg, 0.22 mmol), 2-isopropoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (85 mg, 0.33 mmol), Pd(dppf)Cl2 (8.0 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 (0.50 mL). The mixture was placed in a 60° C. oil bath with stirring for 6 h. The reaction mixture was diluted with EtOAc (4 mL) and the aqueous phase was decanted away. The organic phase was diluted with EtOAc to a volume of 40 mL. The solution was dried over MgSO4; filtered; then concentrated in vacuo to afford a dark residue. This material was subjected to silica gel chromatography (hexanes:EtOAc, 100:0 to 85:15) to afford 2-(4-chloro-6′-isopropoxy-[2,3′-bipyridin]-6-yl)thiazole as a white solid (34 mg, 47%). 1H-NMR (400 MHz, CDCl3) δ 8.92-8.87 (m, 1H), 8.32-8.25 (m, 1H), 8.13 (d, J=1.8 Hz, 1H), 7.96 (d, J=3.0 Hz, 1H), 7.68 (d, J=1.8 Hz, 1H), 7.50 (d, J=3.0 Hz, 1H), 6.82 (dd, J=8.8, 0.5 Hz, 1H), 5.41 (spt, J=6.2 Hz, 1H), 1.41 (d, J=6.3 Hz, 6H).

1. customTo a 2 dram vial equipped with a stir bar
2. customThe vial was capped with a septum
3. customscrew-cap
4. customwas placed in a 60° C.
5. customthe aqueous phase was decanted away
6. additionThe organic phase was diluted with EtOAc to a volume of 40 mL
7. dry with materialThe solution was dried over MgSO4
8. filtrationfiltered
9. concentrationthen concentrated in vacuo
10. customto afford a dark residue