Acetonitrile → Methyl 4-amino-6-(2,3-difluoro-4-(trifluoromethyl)phenyl)-5-fluoro-3-vinylpicolinate

온도

120 °C

In a microwave vessel, a suspension of 2-(2,3-difluoro-4-(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (commercially available) (0.641 g, 2.081 mmol), methyl 4-amino-6-chloro-5-fluoro-3-vinylpicolinate (Head G) (0.4 g, 1.734 mmol), bis(triphenyl phosphine)palladium(II) chloride (0.122 g, 0.173 mmol) and sodium carbonate (0.368 g, 3.47 mmol) in a 3:1 mixture of acetonitrile (3.25 mL) and water (1.084 mL) was stirred under microwave irradiation (120° C., 20 min). The reaction mixture was poured into an half saturated brine solution and was extracted with EtOAc (3×). The combined organic layers were dried over Na2SO4, filtered and concentrated. The residue was purified by preparative reverse phase HPLC (water/acetonitrile gradient) to afford the title compound as a brown solid (0.163 g, 0.433 mmol, 24.98%).

1. extractionwas extracted with EtOAc (3×)
2. dry with materialThe combined organic layers were dried over Na2SO4
3. filtrationfiltered
4. concentrationconcentrated
5. customThe residue was purified by preparative reverse phase HPLC (water/acetonitrile gradient)

ORD 기록

ord-39738c9841774ed2afee354b69b744e9

출처 데이터셋

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09113629B2