1H-Imidazole-4-carbaldehyde → HCID 59728099, Verbindung

HRID 2043350

Reaktionsgleichung

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Br:23])[N:18]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:24]([C:26]1[N:27]=[CH:28][NH:29][CH:30]=1)=O.C([BH3-])#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([N:15]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Br:23])[N:18]=2)[CH2:24][C:26]2[NH:27][CH:28]=[N:29][CH:30]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 40 °C

Versuchsvorschrift

(3-Benzyloxy-phenyl)-(6-bromo-pyridin-2-ylmethyl)-amine (0.10 g, 0.27 mmol) was dissolved in methanol (2 ml). Then 4-formylimidazole (0.13 g, 1.35 mmol), zinc chloride (0.15 g, 1.08 mmol) and sodium cyanoborohydride (0.05 g, 0.81 mmol) were added and the reaction mixture was allowed to stir at 40° C. overnight. After cooling, the reaction mixture was poured onto ammoniumchloride/ice and extracted with ethyl acetate (2 times 50 ml). The organic layer was dried over magnesium sulfate and evaporated. The residue was purified using flash chromatography (SiO2; eluent: methanol/dichloromethane=1:9) to yield an off-white gum (0.11 g, 94%); MS (ISP): 451.1 ([81Br M+H]+), 449.1 ([79Br M+H]+).

Aufarbeitung

temperatureAfter cooling
additionthe reaction mixture was poured onto ammoniumchloride/ice
extractionextracted with ethyl acetate (2 times 50 ml)
dry with materialThe organic layer was dried over magnesium sulfate
customevaporated
customThe residue was purified

Quellen und Nachweise

ORD-Eintrag: ord-8ed97e996e29403eb9a6aa0b5145949f
Quelldatensatz: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08586617B2

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