Ammonium Chloride → 5-bromo-4,6-difluoro-1H-indole

Temperature

110 °C

A solution of 4-bromo-3,5-difluoro-2-[(trimethylsilyl)ethynyl]aniline (1.75 g, 5.77 mmol) in DMF (80 mL) was treated with copper iodide (2.2 g, 11.5 mmol). The reaction mixture was sealed and heated to 110° C. for 3.75 hours. The black reaction mixture was cooled to room temperature, and poured into saturated aqueous ammonium chloride (300 mL). The product was extracted with ethyl acetate/heptane (2:1, 3×200 mL), and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to give a black oil. The crude product was purified using flash chromatography on silica gel, eluting with heptanes/EtOAc (100:0 to 1:1) to give the title compound (350 mg). MS (ES+) 233.9 ((M+2)+H)+

1. customThe reaction mixture was sealed
2. customThe black reaction mixture
3. temperaturewas cooled to room temperature
4. extractionThe product was extracted with ethyl acetate/heptane (2:1, 3×200 mL)
5. dry with materialthe combined organic layers were dried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customto give a black oil
9. customThe crude product was purified
10. washeluting with heptanes/EtOAc (100:0 to 1:1)

ORD record

ord-cfae527fda504f2399f625c2249159f3

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394285B2