Pyridine → 4-(4-Chloro-2-fluorophenoxy)-6-methoxy-7-(trifluoromethylsulphonyloxy)quinazoline

HRID 454072Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 454072
FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.[Cl:16][C:17]1[CH:36]=[CH:35][C:20]([O:21][C:22]2[C:31]3[C:26](=[CH:27][C:28](O)=[C:29]([O:32][CH3:33])[CH:30]=3)[N:25]=[CH:24][N:23]=2)=[C:19]([F:37])[CH:18]=1.N1C=CC=CC=1>C(Cl)Cl>[Cl:16][C:17]1[CH:36]=[CH:35][C:20]([O:21][C:22]2[C:31]3[C:26](=[CH:27][C:28]([O:6][S:7]([C:10]([F:11])([F:12])[F:13])(=[O:8])=[O:9])=[C:29]([O:32][CH3:33])[CH:30]=3)[N:25]=[CH:24][N:23]=2)=[C:19]([F:37])[CH:18]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 1356162044-(4-Chloro-2-fluorophenoxy)-7-hydroxy-6-methoxyquinazoline

Produkt 1

HCID 220308424-(4-Chloro-2-fluorophenoxy)-6-methoxy-7-(trifluoromethylsulphonyloxy)quinazolineAusbeute 88,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

Trifluoromethanesulphonic anhydride (338 mg, 1.2 mmol) was added to a suspension of 4-(4-chloro-2-fluorophenoxy)-7-hydroxy-6-methoxyquinazoline (320 mg, 1 mmol), (prepared as described for the starting material in Example 5), in methylene chloride (2 ml) containing pyridine (2 ml) cooled at 5° C. When the addition was complete, the mixture was left to warm to ambient temperature and stirred for 1 hour. After removal of the volatiles by evaporation, the residue was partitioned between ethyl acetate/ether and water. The organic layer was separated, washed with 0.5M hydrochloric acid, followed by water, brine, dried (MgSO4) and evaporated to give 4-(4-chloro-2-fluorophenoxy)-6-methoxy-7-(trifluoromethylsulphonyloxy)quinazoline (400 mg, 88%).

Aufarbeitung

  1. custom(prepared
  2. additionWhen the addition
  3. waitthe mixture was left
  4. temperatureto warm to ambient temperature
  5. customAfter removal of the volatiles
  6. customby evaporation
  7. customthe residue was partitioned between ethyl acetate/ether and water
  8. customThe organic layer was separated
  9. washwashed with 0.5M hydrochloric acid
  10. dry with materialdried (MgSO4)
  11. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-7b1cb081127d47b5a38aa7318f03f24b
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492560B2

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