4-Aminopyridine → HCID 60004117, Verbindung

HRID 2183467

Reaktionsgleichung

Reaktionsgleichung von HRID 2183467
C(OC(=O)[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12](Br)[CH:11]=1)[CH3:9])(C)(C)C.[NH2:18][C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.C(Cl)Cl.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]>[NH2:7][C@H:8]([C:10]1[CH:11]=[C:12]([NH:18][C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)[CH:13]=[CH:14][CH:15]=1)[CH3:9]

Komponenten

7

Edukt 3

HCID 17274-AminopyridineHCID 62657Potassium Phosphate, TribasicHCID 56971804(S)-N-Boc-1-(3-bromophenyl)ethylamine

Produkt 1

HCID 60004117HCID 60004117, VerbindungAusbeute 103,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A mixture of (S)-[1-(3-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (3 g), 4-aminopyridine (1.88 g), Pd2(dba)3 (915 mg), di-t-butylbiphenylphosphine (298 mg), K3PO4 (4.24 g) in DME (20 mL) was stirred under reflux for 24 h. The reaction mixture was cooled down to room temperature, diluted with methylene chloride, filtered and concentrated in vacuo. The resulting residue was purified by flash chromatography using Biotage eluting with 5% MeOH in ethyl acetate to give the desired product (2.2 g) as a solid.

Aufarbeitung

  1. temperatureunder reflux for 24 h
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was purified by flash chromatography
  5. washeluting with 5% MeOH in ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-73a443b1df5f4abd86a7984885efeef0
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06900210B2

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