2-Aminopyridine → 2-Pyridyl-2-quinolylamine

HRID 404138

Reaktionsgleichung

Reaktionsgleichung von HRID 404138
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1.C(O[K])(C)(C)C>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]>[N:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[NH:12][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Komponenten

7

Edukt 3

HCID 104392-AminopyridineHCID 27627562-BromoquinolineHCID 178418922HCID 178418922, Verbindung

Produkt 1

HCID 53401122-Pyridyl-2-quinolylamineAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-Bromoquinoline, I (500 mg, 2.40 mmol), 2-aminopyridine (249 mg, 2.64 mmol), tBuOK (404 mg, 3.60 mmol), (±)-BINAP (6 mg, 0.01 mmol) and Pd2(dba)3 (5.5 mg, 0.006 mmol) were stirred in toluene (10 mL) at 90° C. under Ar(g) for 21 h. The reaction mixture was then diluted with CH2Cl2 (10 mL) and silica was added, followed by the removal of the solvent under reduced pressure. The resulting dry load material was purified by silica gel column chromatography eluting with CH2Cl2/MeOH (100:1 then 100:2) to furnish II as a colourless oil (344 mg, 45%).

Aufarbeitung

  1. additionwas added
  2. customfollowed by the removal of the solvent under reduced pressure
  3. customThe resulting dry load material
  4. customwas purified by silica gel column chromatography
  5. washeluting with CH2Cl2/MeOH (100:1

Quellen und Nachweise

ORD-Eintrag
ord-b01f6dbe9a5740c582c3a8b9464be9af
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748458B2

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