p-Bromochlorobenzene → 4-(4-Chloro-phenyl)-1H-indole

Temperatur

70 °C

To a mixture of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole (3, 2.43 g, 10 mmol), and 4-bromochlorobenzene (2.87 g, 15 mmol) in THF (34 mL)) were added Palladium catalyst Pd(PPh3)4 (347 mg, 0.3 mmol) and the freshly prepared sodium hydroxide solution (1.20 g, 30 mmol in 14 mL water). The system was degassed and then charged with nitrogen. The degas procedure was repeated for three times. The mixture was stirred under nitrogen at 70° C. oil bath for 15 hours. TLC showed the completion of the coupling reaction. The mixture was cooled to room temperature, diluted with ethyl acetate, and separated from water layer. The ethyl acetate solution was washed by brine, dried over Na2SO4, and concentrated. The crude product was purified by a silica gel column eluting with hexanes—EtOAc (9:1) to provide 2.02 g (89%) of the product 4-(4-chloro-phenyl)-1H-indole as a white solid.

1. customThe system was degassed
2. additioncharged with nitrogen
3. customthe completion of the coupling reaction
4. temperatureThe mixture was cooled to room temperature
5. customseparated from water layer
6. washThe ethyl acetate solution was washed by brine
7. dry with materialdried over Na2SO4
8. concentrationconcentrated
9. customThe crude product was purified by a silica gel column
10. washeluting with hexanes—EtOAc (9:1)

ORD-Eintrag

ord-98ddf42a1a6c4d2689f4364c0f0d50f2

Quelldatensatz

uspto-grants-2004_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06677368B2