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

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).

1. customTo a 2 dram vial equipped with a stir bar
2. customThe vial was capped with a septum screwcap
3. customwas placed in a 60° C.
4. customThe reaction mixture was transfered to a 125 mL separatory funnel
5. washwashed with sat. aq. NaHCO3 (20 mL)
6. extractionThe aq. phase was extracted with EtOAc (20 mL)
7. dry with materialThe combined organics were dried over MgSO4
8. filtrationfiltered
9. concentrationthen concentrated in vacuo
10. customto afford a solid yellow residue

ORD record

ord-768dd89643aa4164a7b3197c3bfe10f9

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09334279B2