Oxazole → Oxazole thiazole indole

HRID 14343

Reaktionsgleichung

Reaktionsgleichung von HRID 14343
[O:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[S:6]1[CH:10]=[CH:9][N:8]=[CH:7]1.[CH2:11]([Li])[CH2:12][CH2:13][CH3:14]>[Cl-].[Zn+2].[Cl-].C1COCC1>[O:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[NH:8]1[C:9]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:2]=[CH:7]1.[S:6]1[CH:10]=[CH:9][N:8]=[CH:7]1

Komponenten

6

Edukt 3

HCID 9255OxazoleHCID 9256ThiazoleHCID 178418339Butyllithium

Produkt 1

HCID 86594208Oxazole thiazole indole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Alternatively, iodo indole 5 is reacted with an alkyl halide, for example as propyl or butyl iodide, bromide, or chloride in the presence of a base, for example sodium hydride or potassium tert-butoxide, more preferably potassium tert-butoxide, in an organic solvent, for example THF, DMF or DMSO, preferably DMSO, at a temperature from room temperature to about 100° C., to yield iodo alkyl 9. An Oxazole or a thiazole in an organic solvent, for example dialkyl ether or THF, at a temperature from about 0 to about −78° C. is reacted with a base, preferably butyl lithium and optionally left stirring for from about 15 to about 60 min. Zinc chloride is then added and the mixture is allowed to warm to 0-30° C., at which time iodo alkyl 9 is added, followed by tetrakis triphenylphosphine palladium. The mixture is then optionally left stirring at a temperature from room temperature to about 80° C. to yield oxazole/thiazole indole 10.The hydrolysis of 10 by methods known to those skilled in the art yields oxazole/thiazole acid 11. Oxazole/thiazole acid 11 is coupled to amine (VIII) using methods known to those skilled in the art.

Aufarbeitung

  1. customfrom about 0 to about −78° C.
  2. waitoptionally left
  3. additionis added
  4. waitThe mixture is then optionally left
  5. stirringstirring at a temperature from room temperature to about 80° C.

Quellen und Nachweise

ORD-Eintrag
ord-9347fa71c7034c56a09f02b9893039a7
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727997B2

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