Sodium Hydroxide → 3-Fluoro-4-(5-(1-phenylcyclohexyl)thiazolo[5,4-b]pyridine-2-yl)benzaldehyde
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]([C:22]2([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[N:16]=3)=[C:9]([F:34])[CH:8]=1.[OH-].[Na+]>C1COCC1>[F:34][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][C:10]=1[C:13]1[S:14][C:15]2[C:20]([N:21]=1)=[CH:19][CH:18]=[C:17]([C:22]1([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1)[N:16]=2)[CH:2]=[O:1]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
A slurry of 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylcyclohexyl)thiazolo[5,4-b]pyridine (0.467 g, 0.984 mmol) in 5 mL 1:1 THF/5N HCl was sealed and heated to 80° C. The resulting yellow solution was allowed to stir 3 h, was cooled, and then was treated with ice and 10N NaOH until basic. The reaction mixture was partitioned between EA and water, washed with water, brine, dried over sodium sulfate, filter, concentrate in vacuo to give 3-fluoro-4-(5-(1-phenylcyclohexyl)thiazolo[5,4-b]pyridine-2-yl)benzaldehyde as an oil/solid that contained some starting material. This material was carried on without further pyrification. MS (ESI) m/z: Calculated: 416.1; Observed: 417.1 (M++1).
Aufarbeitung
- temperaturewas cooled
- customThe reaction mixture was partitioned between EA and water
- washwashed with water, brine
- dry with materialdried over sodium sulfate
- filtrationfilter
- concentrationconcentrate in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-37faf0cc30e4438db0bb53091cb60d56
- Quelldatensatz
- uspto-grants-2010_11
- Patentnummer
- US07842685B2
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