Diisopropylethylamine → Ethyl 2-(2,6-difluorophenyl)thiazole-4-carboxylate

Temperature

120 °C

To a screw-cap vial equipped with a magnetic stir bar, ethyl 2-bromo-1,3-thiazole-4-carboxylate (Ark Pharm, 2.026 g, 8.582 mmol) was added followed by 2-(2,6-difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (Combi-Blocks, 2.47 g, 10.3 mmol) and bis(tri-tert-butylphosphine)palladium (781.8 mg, 1.530 mmol). The vial was sealed with a PTFE-lined septum, and was then evacuated and backfilled with nitrogen three times. 1,4-Dioxane (10.0 mL) was added via syringe, followed by DIPEA (2.41 g, 18.6 mmol) and deoxygenated water (0.60 mL). The reaction mixture was stirred at 120° C. for 3 h. After cooling to room temperature, the mixture was filtered through a silica gel plug (eluted with EtOAc). The filtrate was concentrated under reduced pressure, and the residue was purified by chromatography on silica gel (0-100% EtOAc in hexanes) to give the title compound as a pale yellow oil (1.739 g, 75%). LCMS calc. for C12H10F2NO2S (M+H)+: m/z=270.0. found 270.0.

1. customTo a screw-cap vial equipped with a magnetic stir bar
2. customwas then evacuated
3. addition1,4-Dioxane (10.0 mL) was added via syringe
4. customdeoxygenated water (0.60 mL)
5. temperatureAfter cooling to room temperature
6. filtrationthe mixture was filtered through a silica gel plug (eluted with EtOAc)
7. concentrationThe filtrate was concentrated under reduced pressure
8. customthe residue was purified by chromatography on silica gel (0-100% EtOAc in hexanes)

ORD record

ord-8072fd07cd07493ab1f5afbb61ab0928

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09200004B2