Potassium Carbonate → 3,5-Dimethyl-6-phenanthridinamine

HRID 924570

Reaktionsgleichung

Reaktionsgleichung von HRID 924570
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1B1OC(C)(C)C(C)(C)O1)#[N:2].BrC1C=C(C)C=C(C)[C:20]=1[NH2:21].C(=O)([O-])[O-].[K+].[K+].[C:34]1([CH3:40])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.CO>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:40][C:34]1[CH:39]=[CH:38][C:37]2[C:4]3[C:3]([CH:1]([NH2:2])[N:21]([CH3:20])[C:36]=2[CH:35]=1)=[CH:8][CH:7]=[CH:6][CH:5]=3

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 1705792-Bromo-4,6-dimethylanilineHCID 35702292-(2-Cyanophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 21867641Toluene methanol

Produkt 1

HCID 574535493,5-Dimethyl-6-phenanthridinamineAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418397HCID 178418397, VerbindungKatalysator

Versuchsvorschrift

Added together 2-cyanophenylboronic acid pinacol ester (13.7 g, 60 mmol), 2-bromo-4,6-dimethylaniline (10.0 g, 50 mmol), tetrakis(triphenylphosphine)palladium(0) (2.3 g, 2.0 mmol) and potassium carbonate (18.6 g, 138.21 mol) to a 125 mL of a 95/5 mixture of toluene/methanol. The solvents were degassed and the reaction mixture heated to reflux for 48 hours. After cooling, the reaction mixture was vacuum filtered and the organics evaporated and crude product was purified using silica gel column chromatography treated with triethylamine and 1:9 ethyl acetate and methylene chloride mixture as the eluants. The pure product was collected and concentrated to give 3,5-dimethyl-6-phenanthridinamine (9.1 g, 82% Yield).

Aufarbeitung

  1. customThe solvents were degassed
  2. temperaturethe reaction mixture heated
  3. temperatureto reflux for 48 hours
  4. temperatureAfter cooling
  5. filtrationfiltered
  6. customthe organics evaporated
  7. customcrude product was purified
  8. additiontreated with triethylamine and 1:9 ethyl acetate and methylene chloride mixture as the eluants
  9. customThe pure product was collected
  10. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-643b33daafa24526b8d2b929d014ffc0
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09281483B2

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