Dimethyl Sulfoxide → 6-Formylpyridine-3-carbonitrile

Temperature

150 °C

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.

1. temperatureThe reaction mixture was cooled to room temperature
2. customquenched with 10% aqueous NaHCO3 solution
3. extractionThe organic product was extracted with EtOAc
4. dry with materialthe combined extracts were dried over anhydrous sodium sulfate
5. concentrationconcentrated under reduced pressure

ORD record

ord-d5a0a4c07ae74acc85ff005e7b4e4fed

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08981084B2