2-(Tributylstannyl)-1,3-thiazole → 2-Fluoro-5-(1,3-thiazol-2-yl)pyridine

Temperature

100 °C

To a solution of 5-bromo-2-fluoropyridine (0.5 g, 2.857 mmol) in DMF (6 mL), 2-(tributylstannyl)thiazole (1.3 mL, 4.285 mmol) and Pd(PPh3)2Cl2 (0.2 mg, 0.2857 mmol) were added under argon. The mixture was degassed with argon for 10 min and heated to 100° C. for 30 min. The reaction mixture was filtered through Celite® reagent and the filtrate was diluted with EtOAc (2×100 mL) and water (100 mL). The organic layer was separated, dried over Na2SO4, filtered and concentrated under reduced pressure to obtain crude product. The crude product was purified by Biotage IsoleraOne® column (5% ethyl acetate in hexane) to obtain 2-(6-fluoropyridin-3-yl) thiazole as off-white solid (0.4 g, 80% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.80 (s, 1H), 8.52-8.47 (m, 1H), 7.98 (d, 1H), 7.87 (d, 1H), 7.33 (dd, 1H); LC-MS m/z calculated for [M+H]+ 181.02, found 180.8.

1. customThe mixture was degassed with argon for 10 min
2. filtrationThe reaction mixture was filtered through Celite® reagent
3. additionthe filtrate was diluted with EtOAc (2×100 mL) and water (100 mL)
4. customThe organic layer was separated
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customto obtain crude product
9. customThe crude product was purified by Biotage IsoleraOne® column (5% ethyl acetate in hexane)

ORD record

ord-3c19eb88bb134997b47c5966f6e3852a

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08809372B2