Bromine → HCID 90410358, compound

Temperature

23 °C

Bromine (47 μL, 0.92 mmol, 1.2 equiv) was added to a stirred solution of methyl 4-amino-3-chloro-5-fluoro-6-(4-(trimethylsilyl)phenyl)picolinate (270 mg, 0.77 mmol, 1.0 equiv) in 1,2-dichloroethane (5.1 mL) at 23° C. The resulting dark orange solution was stirred at 23° C. for 24 h. The reaction mixture was quenched with a saturated solution of sodium thiosulfate (5 mL) and then adjusted to pH 10 using 2 M sodium hydroxide. The reaction mixture was diluted with water (50 mL) and extracted with dichloromethane (3×30 mL). The combined organic layers were dried (magnesium sulfate), gravity filtered, and concentrated by rotary evaporation. The residue was purified by reverse phase column chromatography (5% acetonitrile to 100% acetonitrile gradient) to afford the title compound as a tan powder (160 mg, 57%).

1. customThe reaction mixture was quenched with a saturated solution of sodium thiosulfate (5 mL)
2. additionThe reaction mixture was diluted with water (50 mL)
3. extractionextracted with dichloromethane (3×30 mL)
4. dry with materialThe combined organic layers were dried (magnesium sulfate), gravity
5. filtrationfiltered
6. concentrationconcentrated by rotary evaporation
7. customThe residue was purified by reverse phase column chromatography (5% acetonitrile to 100% acetonitrile gradient)

ORD record

ord-4d1dd96a178e4853aa6d51452e1ca922

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09113629B2