Dimethyl Sulfoxide → 6-Formylpyridine-3-carbonitrile
Reaktionsgleichung
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH3:9])=[N:7][CH:8]=1)#[N:2].II.CS(C)=[O:14]>>[CH:9]([C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][N:7]=1)=[O:14]Komponenten
4
Reaktionsbedingungen
- Temperatur
- 150 °C
Versuchsvorschrift
A mixture of 5-cyano-2-methylpyridine (400 mg, 3.38 mmol) and iodine (0.8 g, 3.15 mmol) in DMSO (2 mL) was heated to 150° C. under nitrogen for 20 min. The reaction mixture was cooled to room temperature and quenched with 10% aqueous NaHCO3 solution. The organic product was extracted with EtOAc and the combined extracts were dried over anhydrous sodium sulfate, and concentrated under reduced pressure to get the crude 6-formylnicotinonitrile (400 mg), which was carried through without further purification. 6-Formylnicotinonitrile (400 mg, 3.03 mmol) was dissolved in 1,2-dichloroethane (5 mL) and cooled to 0° C. A solution of tert-butyl 2-methylpiperazine-1-carboxylate (606 mg, 3.03 mmol) in 1,2-dichloroethane (5 mL), followed by sodium triacetoxyborohydride (1.1 g, 5.4 mmol) were added and the reaction mixture was allowed to warm up to room temperature and further stirred for 8 h. The reaction mixture was quenched with 10% aqueous NaHCO3 solution and the product was extracted with EtOAc.