Triethylamine → HCID 66676088, compound

Temperature

70 °C

To a mixture of 2-bromo-4-tert-butyl-5-nitro-phenylamine (27.3 g, 100 mmol) in toluene (200 mL) and water (100 mL) was added Et3N (27.9 mL, 200 mmol), Pd(PPh3)2Cl2 (2.11 g, 3 mmol), CuI (950 mg, 0.5 mmol) and trimethylsilyl acetylene (21.2 mL, 150 mmol) under a nitrogen atmosphere. The reaction mixture was heated at 70° C. in a sealed pressure flask for 2.5 h., cooled down to room temperature and filtered through a short plug of Celite. The filter cake was washed with EtOAc. The combined filtrate was washed with 5% NH4OH solution and water, dried over Na2SO4 and concentrated. The crude product was purified by column chromatography (0-10% EtOAc/petroleum ether) to provide 4-tert-butyl-5-nitro-2-trimethylsilanylethynyl-phenylamine as a brown viscous liquid (25 g, 81%).

1. temperaturecooled down to room temperature
2. filtrationfiltered through a short plug of Celite
3. washThe filter cake was washed with EtOAc
4. washThe combined filtrate was washed with 5% NH4OH solution and water
5. dry with materialdried over Na2SO4
6. concentrationconcentrated
7. customThe crude product was purified by column chromatography (0-10% EtOAc/petroleum ether)

ORD record

ord-ea08863f99d04d5b8670fba50ccae782

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08829204B2