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Toluene → HCID 68736170, Verbindung

HRID 1514017
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1514017
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1B(O)O.[NH2:12][C:13]1[C:14](Br)=[N:15][CH:16]=[CH:17][CH:18]=1.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1>O.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(OC)=CC=CC=2OC)CCCCC1>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:14]1[C:13]([NH2:12])=[CH:18][CH:17]=[CH:16][N:15]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 1140TolueneHCID 6428163-Amino-2-bromopyridineHCID 27735432-(Methylthio)benzeneboronic acidHCID 22031701Potassium phosphate, tribasic, monohydrate

Produkt 1

HCID 68736170HCID 68736170, VerbindungAusbeute 78,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564
Bis(dibenzylideneacetone)palladium
Katalysator
HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylKatalysator
HCID 962WaterLösungsmittel

Versuchsvorschrift

The 500 mL round-bottom flask, equipped with magnetic stirrer and reflux condenser was charged with 2-(methylthio)phenylboronic acid (9.48 g, 56 mmol), 3-amino-2-bromopyridine (7.15 g, 57 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos, 0.92 g, 4 mol %), Pd2(dba)3 (1.02 g, 2 mol %), potassium phosphate hydrate (39 g, 3 equivalents), 100 mL of toluene. The flask was filled with nitrogen and heated to reflux under nitrogen atmosphere for 24 hours. Then the reaction was cooled down to room temperature, diluted with 500 ml of water and extracted with ethyl acetate (5×40 mL). Organic fractions were combined, dried over sodium sulfate, filtered and evaporated. The residue was subjected to column chromatography on silica gel with eluent hexane/ethyl acetate gradient mixture, providing 2-(2-(methylthio)phenyl)pyridin-3-amine as yellow crystals (9.5 g). NMR confirmed the structure.

Aufarbeitung

  1. customThe 500 mL round-bottom flask, equipped with magnetic stirrer
  2. temperaturereflux condenser
  3. additionThe flask was filled with nitrogen
  4. temperatureheated
  5. temperatureto reflux under nitrogen atmosphere for 24 hours
  6. extractionextracted with ethyl acetate (5×40 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-c8b8bad228ae44208baff98433ad9c39
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08221905B2

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