Dimethyl Sulfoxide → 5-Chloro-7-methyl-1-tosyl-1H-indole-4-carbaldehyde
Reaktionsgleichung
[Cl:1][C:2]1[C:3]([CH2:22][OH:23])=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[N:7]([S:12]([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.C(N(C(C)C)C(C)C)C.CS(C)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]2[N:7]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:6]=[CH:5][C:4]=2[C:3]=1[CH:22]=[O:23]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a solution of (5-chloro-7-methyl-1-tosyl-1H-indol-4-yl)methanol (3.3 g, 9.5 mmol) and N-ethyl-diisopropylamine (8.3 mL, 47.3 mmol) in CH2Cl2 (20 mL)/DMSO (1 mL) was added SO3.Py (4.5 g, 28.4 mmol) at 0° C. The mixture was stirred at 0° C. for 2.5 h, and then stirred at room temperature for 15 h. The reaction was quenched by MeOH. The mixture was stirred for 1 h. The mixture was partially concentrated. The mixture was diluted with H2O, and then the resulted solid was collected by filtration. The resulting residue was triturated with MeOH to give the title compound. 1H NMR (400 MHz, ACETONITRILE-d3) δ 10.56 (s, 1H), 8.00 (d, J=3.80 Hz, 1H), 7.62 (d, J=3.80 Hz, 1H), 7.60 (d, J=8.60 Hz, 2H), 7.35 (d, J=8.60 Hz, 2H), 7.22 (s, 1H), 2.60 (s, 3H), 2.37 (s, 3H).
Aufarbeitung
- stirringstirred at room temperature for 15 h
- customThe reaction was quenched by MeOH
- stirringThe mixture was stirred for 1 h
- concentrationThe mixture was partially concentrated
- additionThe mixture was diluted with H2O
- filtrationthe resulted solid was collected by filtration
- customThe resulting residue was triturated with MeOH
Quellen und Nachweise
- ORD-Eintrag
- ord-1b97057e36da46349d4921b5ea1ec617
- Quelldatensatz
- uspto-grants-2015_06
- Patentnummer
- US09056874B2
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