Potassium Hydroxide → 5-((4-fluorophenyl)ethynyl)-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-carboxylic acid
Reaktionsgleichung
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][N:10]2[C:18]3[CH:17]=[CH:16][C:15]([C:19]([O:21]C)=[O:20])=[CH:14][C:13]=3[C:12]3[CH2:23][N:24]([CH3:27])[CH2:25][CH2:26][C:11]2=3)=[CH:4][CH:3]=1.[OH-].[K+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][N:10]2[C:18]3[CH:17]=[CH:16][C:15]([C:19]([OH:21])=[O:20])=[CH:14][C:13]=3[C:12]3[CH2:23][N:24]([CH3:27])[CH2:25][CH2:26][C:11]2=3)=[CH:4][CH:3]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
Methyl 5-((4-fluorophenyl)ethynyl)-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-carboxylate (0.280 g) was dissolved in MeOH (10 mL) and added 10% aq. KOH solution (5 mL). The reaction mixture was heated at 50° C. for 48 h. Progress of the reaction was monitored by TLC and LCMS. The solvent was evaporated and the residue acidified with 1% aq. HCl solution. The solid was filtered and the residue was washed with water (2-3×). The product was washed with hexane. The product was obtained as a white solid. 1H NMR (CD3OD, freebase) δ (ppm): 8.30 (d, 1H), 8.10 (m, 1H), 7.70 (m, 3H), 7.20 (m, 2H), 4.60 (m, 2H), 3.80 (m, 2H), 3.38 (m, 2H), 3.15 (s, 3H).
Aufarbeitung
- customThe solvent was evaporated
- filtrationThe solid was filtered
- washthe residue was washed with water (2-3×)
- washThe product was washed with hexane
- customThe product was obtained as a white solid
Quellen und Nachweise
- ORD-Eintrag
- ord-be844365c32441f19f3345ae91875f23
- Quelldatensatz
- uspto-grants-2014_12
- Patentnummer
- US08907097B2
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