HCID 86731995, compound → HCID 86731994, compound

Temperature

50 °C

A suspension of 6-bromo-4-nitro-N-[4-(trifluoromethyl)pyridin-2-yl]pyridin-2-amine (586 mg, 1.614 mmol) and iron (361 mg, 6.46 mmol) in acetic acid (7 mL) was heated to 50° C. for 1 hour. The reaction mixture was partitioned between ethyl acetate (70 mL) and water (70 mL). The aqueous layer was further extracted with ethyl acetate (70 mL), and the combined organic layers were washed with water (70 mL), saturated aqueous sodium bicarbonate solution (2×70 mL), brine (50 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (10-60% ethyl acetate/hexanes) to afford 6-bromo-N2-[4-(trifluoromethyl)pyridin-2-yl]pyridine-2,4-diamine MS ESI calc'd. for C11H9BrF3N4 [M+H]+ 333 and 335. found 333 and 335. 1H NMR (500 MHz, DMSO-d6) δ 11.08 (s, 1H), 8.63 (s, 1H), 8.59 (d, J=5.4 Hz, 1H), 7.85 (s, 1H), 7.83-7.76 (m, 2H), 7.48-7.42 (m, 1H), 7.37-7.32 (m, 1H).

1. customThe reaction mixture was partitioned between ethyl acetate (70 mL) and water (70 mL)
2. extractionThe aqueous layer was further extracted with ethyl acetate (70 mL)
3. washthe combined organic layers were washed with water (70 mL), saturated aqueous sodium bicarbonate solution (2×70 mL), brine (50 mL)
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by chromatography on silica gel (10-60% ethyl acetate/hexanes)

ORD record

ord-6277df5e742d4941b45b2434cb55af57

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09242984B2