Dimethylformamide → 5-Chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine-3-carbaldehyde
Reaktionsgleichung
P(Cl)(Cl)(Cl)=O.[Cl:6][C:7]1[CH:12]=[CH:11][N:10]2[N:13]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH:15]=[C:9]2[CH:8]=1.[OH-].[NH4+].CN(C)[CH:27]=[O:28]>>[Cl:6][C:7]1[CH:12]=[CH:11][N:10]2[N:13]=[C:14]([C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[C:15]([CH:27]=[O:28])=[C:9]2[CH:8]=1Komponenten
Versuchsvorschrift
Phosphorous oxychloride (0.6 mL, 6.4 mmol) was added to N,N-dimethylformamide (10 mL) and the resulting mixture stirred at room temperature for 10 minutes. 5-Chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridine (1.0 g, 4.1 mmol) was added and the reaction mixture was stirred at room temperature for 12 hours. The reaction mixture was poured into ice-water and neutralized to pH 7 with aquous ammonium hydroxide. The resulting slurry was extracted with dichloromethane (3×40 mL). The combined organics were washed with brine, dried (magnesium sulfate), filtered and concentrated to give, after recrystallization from acetonitrile, 5-chloro-2-(4fluorophenyl)pyrazolo [1,5-α]pyridine-3-carbaldehyde (0.95 g, 85%) as a white solid. 1H-NMR (CDCl3): δ10.07 (s, 1H),18.49 (d, 1H), 8.44 (d, 11H), 7.78 (q, 2H), 7.22 (t, 2H), 7.07 (dd, 1 H); MS m/z 275 (M+1).
Aufarbeitung
- stirringthe reaction mixture was stirred at room temperature for 12 hours
- extractionThe resulting slurry was extracted with dichloromethane (3×40 mL)
- washThe combined organics were washed with brine
- dry with materialdried (magnesium sulfate)
- filtrationfiltered
- concentrationconcentrated
- customto give
- customafter recrystallization from acetonitrile, 5-chloro-2-(4fluorophenyl)pyrazolo [1,5-α]pyridine-3-carbaldehyde (0.95 g, 85%) as a white solid
Quellen und Nachweise
- ORD-Eintrag
- ord-9dd927b9d0ef4882bfcfbe35c38a9c3d
- Quelldatensatz
- uspto-grants-2006_08
- Patentnummer
- US07087618B2
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