Tetrahydrofuran → N2-(4-chloro-3,5-difluorophenyl)pyridine-2,3-diamine

To a solution of N-(4-chloro-3,5-difluorophenyl)-3-nitropyridin-2-amine (C17) (100 mg, 0.35 mmol) in a 1:1 mixture of tetrahydrofuran and water (20 mL) was added ammonium chloride (148 mg, 2.77 mmol) followed by zinc (182 mg, 2.78 mmol), and the reaction mixture was stirred at room temperature for 2 hours. It was then diluted with water (10 mL) and extracted with ethyl acetate (3×20 mL); the combined organic layers were washed with saturated aqueous sodium chloride solution (20 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to afford the product as a yellow solid. This material was used directly in the following step. Yield: 80 mg, 0.31 mmol, 89%.

1. extractionextracted with ethyl acetate (3×20 mL)
2. washthe combined organic layers were washed with saturated aqueous sodium chloride solution (20 mL)
3. dry with materialdried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated in vacuo

ORD record

ord-6bc6b0526cdc4328bb9593a658ac1782

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09120788B2