Sodium Carbonate → N-[4-(5-formyl-4-phenyl-1,3-thiazol-2-yl)pyridin-2-yl]acetamide

Temperature

80 °C

Tris(dibenzylideneacetone)dipalladium(0) (0.0162 g, 0.0177 mmol) and tri-t-butylphosphonium tetrafluoroborate (0.0103 g, 0.0355 mmol) were weighed into a round bottom flask and dissolved in DME (3 mL). The mixture was sonicated for 15 min under atmosphere of Argon. After addition of water (1 mL), sodium carbonate (0.226 g, 2.13 mmol) was added to the dark purple solution followed by phenylboronic acid (0.173 g, 1.42 mmol) and N-[4-(4-chloro-5-formyl-1,3-thiazol-2-yl)pyridin-2-yl]acetamide (0.200 g, 0.710 mmol). The resulting mixture was stirred for 10 h at 80° C., cooled to room temperature, diluted with water and extracted with DCM (3×5 mL). The organics were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The result mixture was purified by ISCO column with 0-5% MeOH in DCM in 10 min. Fractions containing product were combined and solvent was removed under reduced pressure to give crude material (0.099 g, 43%), which was used in the next step without further purification. LCMS: (FA) ES+ 324.

1. customThe mixture was sonicated for 15 min under atmosphere of Argon
2. additionwas added to the dark purple solution
3. temperaturecooled to room temperature
4. extractionextracted with DCM (3×5 mL)
5. washThe organics were washed with brine
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customThe result mixture was purified by ISCO column with 0-5% MeOH in DCM in 10 min
10. additionFractions containing product
11. customsolvent was removed under reduced pressure

ORD record

ord-70c07393af3d4f9494279ceac216106a

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09139589B2