2,6-Di-tert-butyl-4-methylphenol → 5-(5-Cyanopyrid-3-yl)-3-(N-methylpyrrolidin-3-yl)-1H-indole

HRID 1604280Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1604280
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]1[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12]1.[C:17]([C:19]1[CH:20]=[C:21]([Sn](C)(C)C)[CH:22]=[N:23][CH:24]=1)#[N:18].[Cl-].[Li+].C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(N(CC)CC)C>[C:17]([C:19]1[CH:20]=[C:21]([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[C:5]3[CH:11]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12]2)[CH:22]=[N:23][CH:24]=1)#[N:18]

Komponenten

7

Edukt 4

HCID 314042,6-Di-tert-butyl-4-methylphenolHCID 433294Lithium ChlorideHCID 153262755-bromo-3-(N-methylpyrrolidin-3-yl)1H-indoleHCID 186990455-(Trimethylstannyl)nicotinonitrile

Produkt 1

HCID 154342745-(5-Cyanopyrid-3-yl)-3-(N-methylpyrrolidin-3-yl)-1H-indoleAusbeute 11,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of 5-bromo-3-(N-methylpyrrolidin-3-yl)-1H-indole (0.500 g, 1.79 mmol), 5-cyano-3-trimethylstannylpyridine (0.525 g, 1.97 mmol, 1.1 eq), bis(triphenylphosphine)palladium(II) chloride (0.628 g, 0.90 mmol, 0.5 eq), triethylamine (1.19 mL, 8.59 mmol, 4.8 eq, lithium chloride (0.235 g, 5.55 mmol, 3.1 eq), and 2,6-di-tert-butyl-4-methylphenol (40 mg) in anhydrous acetontrile (5 mL) was heated at reflux under nitrogen for 20 hours. The resulting reaction mixture was evaporated under reduced pressure, and the residue was column chromatographed using silica gel (approx 50 g) and elution with 9:1:0.1 [methylene chloride/methanol/ammonium hydroxide] to afford the title compound (0.060 g, 0.20 mmol, 11%) as a clear, pale brown oil: LRMS (m/z, relative intensity) 302 (M+, 29), 245 (8), 57 (100); HRMS calculated for C19H18N4 302.1528, found 302.1533.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 20 hours
  3. customThe resulting reaction mixture
  4. customwas evaporated under reduced pressure
  5. customchromatographed
  6. washsilica gel (approx 50 g) and elution with 9:1:0.1 [methylene chloride/methanol/ammonium hydroxide]

Quellen und Nachweise

ORD-Eintrag
ord-f4263c8ffe1445dabaaa09f1f5a0e043
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05994352

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