2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-chlorothiazolo[5,4-b]pyridine → 4-(5-Chlorothiazolo[5,4-b]pyridine-2-yl)-3-fluorobenzaldehyde
Reaktionsgleichung
[O:1]1CCCO[CH:2]1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]3[C:20]([N:21]=2)=[CH:19][CH:18]=[C:17]([Cl:22])[N:16]=3)=[C:9]([F:23])[CH:8]=1>C1COCC1>[Cl:22][C:17]1[N:16]=[C:15]2[S:14][C:13]([C:10]3[CH:11]=[CH:12][C:7]([CH:2]=[O:1])=[CH:8][C:9]=3[F:23])=[N:21][C:20]2=[CH:19][CH:18]=1Komponenten
3
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A slurry of 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-chlorothiazolo[5,4-b]pyridine (5.00 g, 14.3 mmol) in 100 mL 1:1 THF/5N aq. HCl was heated in a sealed tube to 70° C. The thick orange mixture was cooled slightly and an additional 50 mL THF was added. The reaction mixture was sealed and heating continued. After 2 h, the reaction mixture was cooled and allowed to stir 3 days at ambient temperature. The reaction mixture was cooled and THF was removed in vacuo. The resulting yellow solid was collected by filtration through a frit, rinsing with water. The material was dried on the frit for several hours and dried in vacuo overnight to give 4-(5-chlorothiazolo[5,4-b]pyridine-2-yl)-3-fluorobenzaldehyde as a light yellow/orange solid. MS (ESI) m/z: calculated: 292.0: Observed: 292.9 (M++1).