Aniline → Phenyl-(1-triisopropylsilanyl-1H-indol-4-yl)-amine

HRID 268761Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 268761
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[Si:18]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20].C([O-])([O-])=O.[K+].[K+]>CC(O)(C)C>[C:2]1([NH:1][C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH:11]=[CH:12][N:13]3[Si:18]([CH:22]([CH3:24])[CH3:23])([CH:25]([CH3:27])[CH3:26])[CH:19]([CH3:20])[CH3:21])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 6115AnilineHCID 11430Potassium CarbonateHCID 27955734-bromo-1-(triisopropylsilyl)-1H-indole

Produkt 1

HCID 59831613Phenyl-(1-triisopropylsilanyl-1H-indol-4-yl)-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Aniline (328 μl, 3.6 mmol) was added to a room temperature mixture of 4-bromo-1-triisopropylsilanyl-1H-indole (1.06 g, 3 mmol), tris(dibenzylideneacetone)dipalladium 2-(dicyclohexylphosphino)-2,4,6-triisopropyl-1,1′-biphenylphosphine (Pd2(dba)3, 27.5 mg, 0.03 mmol), (72 mg, 0.05 mmol) and K2CO3 (1.04 g, 7.5 mmol) in t-BuOH (14 ml). The reaction mixture was stirred at 110° C. for 4 hours. The reaction was cooled, and the solid was filtered off. The filtrate was concentrated and the residue was partitioned between EtOAc and a saturated solution of NaHCO3. The aqueous layer was extracted twice with EtOAc. The combined organic layers were dried over Na2SO4, filtered, concentrated, and purified via flash chromatography (hexane/EtOAc) affording the compound XXI as a yellow oil in quantitative yield (1.09 g).

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. filtrationthe solid was filtered off
  3. concentrationThe filtrate was concentrated
  4. customthe residue was partitioned between EtOAc
  5. extractionThe aqueous layer was extracted twice with EtOAc
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified via flash chromatography (hexane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-6ffbe1855af64e399956cba235bb565e
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07446118B2

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