Pyridine-2-carbonitrile → HCID 178504797, compound

To a suspension of 4-(methylsulfonyl)aniline hydrochloride (6 g, 28.8 mmol) in toluene (150 ml) at 0° C., trimethylaluminum (2M solution in toluene, 21.6 ml, 43.2 mmol) was added over 15 minutes. The reaction mixture was warmed to room temperature and stirred for 2.5 hours. A solution of 2-cyanopyridine (6 g, 57.6 mmol) in toluene (150 ml) was added over 10 minutes and the reaction mixture was heated to 85–90° C. After 24 hours, the reaction mixture was cooled to room, temperature and poured over a slurry of silica gel in chloroform. After filtration, the residue was washed with a mixture of methylene chloride/methanol and later methanol. The combined filtrates were concentrated and the resulting yellowish solid was stirred with ethyl acetate (1500 ml) and filtered. The pale yellow solid (5.2 g, 66%) was used in the next reaction without further purification.

1. temperaturethe reaction mixture was heated to 85–90° C
2. waitAfter 24 hours
3. temperaturethe reaction mixture was cooled to room, temperature
4. filtrationAfter filtration
5. washthe residue was washed with a mixture of methylene chloride/methanol and later methanol
6. concentrationThe combined filtrates were concentrated
7. stirringthe resulting yellowish solid was stirred with ethyl acetate (1500 ml)
8. filtrationfiltered
9. customThe pale yellow solid (5.2 g, 66%) was used in the next reaction without further purification

ORD record

ord-f86ade92914a41268f9c1f2674217948

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07220770B2