2-Aminopyridine → HCID 86660143, Verbindung

HRID 404152

Reaktionsgleichung

Reaktionsgleichung von HRID 404152
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12](Br)=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=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]>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 3

HCID 104392-AminopyridineHCID 160946965-(Benzyloxy)-2-bromopyridineHCID 178418922HCID 178418922, Verbindung

Produkt 1

HCID 86660143HCID 86660143, VerbindungAusbeute 91,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Compound I (370 mg, 1.40 mmol), 2-aminopyridine (145 mg, 1.54 mmol), tBuOK (235 mg, 2.10 mmol), (±)-BINAP (35 mg, 0.01 mmol) and Pd2(dba)3 (32 mg, 0.006 mmol) were stirred in toluene (5 mL) at 90° C. under Ar(g) for 17 h. The reaction mixture was then diluted with CH2Cl2 (5 mL), and silica was added followed by the removal of the solvent under reduced pressure. The resulting dry loaded material was purified by silica gel column chromatography eluting with hexane/EtOAc (60:40 then 50:50) to furnish II as a colourless oil (355 mg, 91%).

Aufarbeitung

  1. additionwas added
  2. customfollowed by the removal of the solvent under reduced pressure
  3. customThe resulting dry
  4. customwas purified by silica gel column chromatography
  5. washeluting with hexane/EtOAc (60:40

Quellen und Nachweise

ORD-Eintrag
ord-950f928aefd640b18761458fd45fa7d6
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748458B2

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