1,4-Dibromobenzene → 4-(3-Bromo-phenyl)-1H-indole

HRID 1839578

Reaktionsgleichung

CC1(C)C(C)(C)OB([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH:11]=[CH:12][NH:13]3)O1.[Br:19][C:20]1[CH:25]=[CH:24][C:23](Br)=[CH:22][CH:21]=1.[OH-].[Na+]>C1COCC1.[Pd].C(OCC)(=O)C>[Br:19][C:20]1[CH:21]=[C:22]([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH:11]=[CH:12][NH:13]3)[CH:23]=[CH:24][CH:25]=1

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

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 1,4-dibromobenzene (11.8 g, 50 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 (74%) of the product 4-(3-bromo-phenyl)-1H-indole as a white solid.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-b43b3da77a6942a08571cfafb4137235
Quelldatensatz: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06677368B2

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