Indole → N-(4-methylphenyl)indole

HRID 1296995

Reaktionsgleichung

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Cl[C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1.CC([O-])(C)C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2OC)CCCCC1.C1(C)C=CC=CC=1>[CH3:17][C:14]1[CH:15]=[CH:16][C:11]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)=[CH:12][CH:13]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

An oven-dried test tube was purged with argon and then charged with 2-dicyclohexylphosphino-2′-methoxy-1,1′-biphenyl (14.5 mg, 0.038 mmol, 7.5 mol %) and Pd2(dba)3 (11.6 mg, 0.013 mmol, 5.0 mol % Pd). Toluene (1.0 mL), indole (71 mg, 0.61 mmol), 4-chlorotoluene (60 mL, 0.51 mmol), and NaOt-Bu (70 mg, 0.73 mmol) were then added. The tube was fitted with a septum, purged with argon and heated at 100° C. for 28 h. The reaction was then cooled to room temperature, diluted with ether (20 mL), filtered through Celite and concentrated in vacuo. The residue was purified by flash chromatography on silica gel to afford 99 mg (94%) of a colorless oil.

Aufarbeitung

customAn oven-dried test tube was purged with argon
customThe tube was fitted with a septum
custompurged with argon
temperatureThe reaction was then cooled to room temperature
additiondiluted with ether (20 mL)
filtrationfiltered through Celite
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag: ord-64f2bd6e18764b81b7070c5cdc841e98
Quelldatensatz: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07247731B2

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