Benzene, 1-bromo-3-nitro- → HCID 67390544, Verbindung

Temperatur

40 °C

A solution of BINAP (0.47 g, 0.75 mmol) and tris(dibenzylideneacetone)dipalladium (0) (0.34 g, 0.37 mmol) in toluene (120 mL) was heated to 90° C. during 15 minutes under nitrogen. The reaction mixture was cooled to 40° C. before adding 1-bromo-3-nitrobenzene (1.89 g, 9.37 mmol), (1S,4S)-2-isopropyl-2,5-diazabicyclo[2.2.1]heptane dihydrochloride (2.0 g, 9.37 mmol) and sodium tert-butoxide (3.14 g, 32.74 mmol). The reaction was heated to 90° C. during 18 hours under nitrogen. After return to room temperature, the reaction was diluted with ethyl acetate and filtered through celite. The filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with a mixture of DCM/7N NH3 in methanol (96/4) to afford the title compound (1.92 g, 78%).

1. temperatureThe reaction was heated to 90° C. during 18 hours under nitrogen
2. filtrationfiltered through celite
3. concentrationThe filtrate was concentrated under reduced pressure
4. customThe residue was purified by flash chromatography on silica gel eluting with a mixture of DCM/7N NH3 in methanol (96/4)

ORD-Eintrag

ord-5062982f87b649e18fdc2b7e7420f1f6

Quelldatensatz

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08012983B2