6-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde → 6-bromo-3-methyl-1H-pyrrolo[2,3-b]pyridine
Reaktionsgleichung
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Br:7][C:8]1[N:13]=[C:12]2[NH:14][CH:15]=[C:16]([CH:17]=O)[C:11]2=[CH:10][CH:9]=1>C1COCC1>[Br:7][C:8]1[N:13]=[C:12]2[NH:14][CH:15]=[C:16]([CH3:17])[C:11]2=[CH:10][CH:9]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
LAH (1.0M in THF, 4.45 mL, 4.45 mmol) was added dropwise to refluxing 6-bromo-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (1000 mg, 4.45 mmol) in dry THF (16 mL). The mixture was refluxed for 1 h, allowed to attain room temperature, and quenched with water (0.34 mL), w/w 15% aq. NaOH (0.34 mL) and water (1 mL). The resulting precipitation was filtered off, the filtrate concentrated and the residue was partitioned between aqueous NaOH and DCM. The organic layers were combined, dried and concentrated to give title compound. LCMS-ESI+: calc'd for C8H7BrN2: 211.2 (M+H+); Found: 211.2 (M+H+).