Acetic Anhydride → (E)-methyl 1-acetyl-3-(ethoxy(phenyl)methylene)-2-oxo-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine-6-carboxylate
Reaktionsgleichung
[O:1]=[C:2]1[NH:10][C:9]2[CH:8]=[C:7]([C:11]([O:13][CH3:14])=[O:12])[N:6]=[CH:5][C:4]=2[CH2:3]1.[CH3:15][C:16](OC(C)=O)=[O:17].[CH3:22][CH2:23][O:24][C:25](OCC)(OCC)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1(C)C=CC=CC=1>[C:16]([N:10]1[C:9]2[CH:8]=[C:7]([C:11]([O:13][CH3:14])=[O:12])[N:6]=[CH:5][C:4]=2/[C:3](=[C:25](\[O:24][CH2:23][CH3:22])/[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)/[C:2]1=[O:1])(=[O:17])[CH3:15]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 85 °C
Versuchsvorschrift
Step-1: To a solution of methyl 2-oxo-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine-6-carboxylate (10 mg, 0.052 mmol) in toluene (5 mL) was added Ac2O (15 mg, 0.156 mmol) and triethyl orthobenzoate (35 mg, 0.156 mmol) at room temperature. The reaction mixture was heated stirred at 85° C. for 3 h. The solvent was evaporated under reduced pressure and the resulting residue was purified by silica gel column chromatography using 5% acetone in dichloromethane to afford (E)-methyl 1-acetyl-3-(ethoxy(phenyl)methylene)-2-oxo-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine-6-carboxylate as yellow solid. 1H NMR (CDCl3, 400 MHz) δ 9.15 (s, 1H), 8.67 (s, 1H), 7.52-7.59 (m, 5H), 4.06 (dd, J=13.9, 7 Hz), 3.89 (s, 3H), 2.45 (s, 3H), 1.37 (t, J=7 Hz, 3H).
Aufarbeitung
- temperatureThe reaction mixture was heated
- customThe solvent was evaporated under reduced pressure
- customthe resulting residue was purified by silica gel column chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-c9bf65d5d50f4b4f8e2c9bd65e7a6489
- Quelldatensatz
- uspto-grants-2015_05
- Patentnummer
- US09040555B2
Notizen zur Reaktion
Wird geladen…