2-Fluoroaniline → HCID 117771064, compound

Temperature

130 °C

A mixture of 3-amino-6-bromopicolinic acid (250 mg, 1.152 mmol) and SOCl2 (5 mL) in toluene (10 mL) was stirred at 130° C. for 2 h, then evaporated and dissolved in tetrahydrofuran (20 mL). 2-fluoro-phenylamine (256 mg, 2.3 mmol) was added dropwise maintaining the temperature at 5° C. The reaction mixture was heated to 90° C. for 15 h. The mixture was cooled to room temperature and quenched with saturated aqueous K2CO3 (10 mL) and extracted with ethyl acetate (10 mL*3), the combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified with column chromatograph (PE:EtOAc=3:1) to give 3-amino-6-bromo-N-(2-fluorophenyl)picolinamide (160 mg, yield: 45%). MS (M+H)+: 311/313.

1. customevaporated
2. dissolutiondissolved in tetrahydrofuran (20 mL)
3. temperaturemaintaining the temperature at 5° C
4. temperatureThe reaction mixture was heated to 90° C. for 15 h
5. temperatureThe mixture was cooled to room temperature
6. customquenched with saturated aqueous K2CO3 (10 mL)
7. extractionextracted with ethyl acetate (10 mL*3)
8. washthe combined organic layers were washed with brine
9. dry with materialdried over anhydrous sodium sulfate
10. filtrationfiltered
11. concentrationconcentrated
12. customThe residue was purified with column chromatograph (PE:EtOAc=3:1)

ORD record

ord-993ad29fe5624e4bab27df1bdf77d34e

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09364482B2