2-Aminopyridine → HCID 58545058, Verbindung

HRID 404147

Reaktionsgleichung

Reaktionsgleichung von HRID 404147
Br[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1.CC(C)([O-])C.[K+]>C1(C)C=CC=CC=1.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]>[C:8]1([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[CH:7]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

7

Edukt 3

HCID 104392-AminopyridineHCID 1047002-Bromo-4-phenylpyridineHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 58545058HCID 58545058, VerbindungAusbeute 62,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-Bromo-4-phenylpyridine (280 mg, 1.19 mmol), 2-aminopyridine (124 mg, 1.31 mmol), potassium tert-butoxide (201 mg, 1.79 mmol), (±)-BINAP (3 mg, 0.05 mmol) and Pd2(dba)3 (2.7 mg, 0.03 mmol) were stirred in toluene (2.5 mL) at 90° C. under Ar(g). After 17 h stirring, the reaction mixture was diluted with CH2Cl2 (2.5 mL) and silica was added. The solvent was removed under reduced pressure and the resulting dry loaded material purified by silica gel column chromatography, eluting with CH2Cl2/MeOH (100:2), to furnish I as a yellow solid (183 mg, 62%).

Aufarbeitung

  1. additionwas added
  2. customThe solvent was removed under reduced pressure
  3. customthe resulting dry
  4. custompurified by silica gel column chromatography
  5. washeluting with CH2Cl2/MeOH (100:2)

Quellen und Nachweise

ORD-Eintrag
ord-12d4c056b99b495e824f039e45e5457c
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748458B2

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