Reaktionsgleichung
CO[C:3]([C:5]1[CH:10]=[CH:9][N:8]2[CH:11]=[CH:12][N:13]=[C:7]2[CH:6]=1)=[O:4].[CH3:14][N:15](C)[OH:16].[CH3:18][Al](C)C.CCCCCC>C(Cl)Cl>[CH3:18][O:16][N:15]([CH3:14])[C:3]([C:5]1[CH:10]=[CH:9][N:8]2[CH:11]=[CH:12][N:13]=[C:7]2[CH:6]=1)=[O:4]Komponenten
6
Versuchsvorschrift
To a solution of Imidazo[1,2-a]pyridine-7-carboxylic acid methyl ester (0.67 g, 3.83 mmol) and dimethylhydroxylamine (0.93 g, 9.57 mmol) in CH2Cl2 (40 ml) at 0° C. was added 2M trimethylaluminium solution in hexane (3.8 ml, 9.57 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 1 h, before being cooled back to 0° C. and quenched with ice. The reaction was filtered and liquid fraction partitioned between CH2Cl2/H2O. The organic layer was separated, dried (MgSO4), filtered and the solvent removed in vacuo to afford the crude product. The residue was purified by silica column chromatography (0-50% MeOH in Et2O) to afford the product (187 mg). MS: [M+H]+=206.
Aufarbeitung
- temperaturebefore being cooled back to 0° C.
- customquenched with ice
- filtrationThe reaction was filtered
- customliquid fraction partitioned between CH2Cl2/H2O
- customThe organic layer was separated
- dry with materialdried (MgSO4)
- filtrationfiltered
- customthe solvent removed in vacuo
- customto afford the crude product
- customThe residue was purified by silica column chromatography (0-50% MeOH in Et2O)
Quellen und Nachweise
- ORD-Eintrag
- ord-f187bdd8f00149fabc0c4d5902353323
- Quelldatensatz
- uspto-grants-2014_11
- Patentnummer
- US08895745B2
Verknüpfte Notizen
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