Dimethylformamide → 3-Aminopyridine-2-carbonitrile

Temperature

90 °C

2-Chloro-pyridin-3-ylamine (2.0 g) was dissolved in DMF (24 mL) and zinc cyanide (1.83 g) was added to the solution. The solution was degassed in vacuum 5×, tetrakis(triphenylphosphine) palladium(0) (901 mg) was added and the reaction mixture was stirred at 90° C. for 7 h. After the reaction mixture was cooled to room temperature, the solid was removed by filtration and the filter cake was washed with ethyl acetate. Water was added to the filtrate, the layers were separated and the aqueous layer was 2× extracted with ethyl acetate. The combined organic layer was washed 3× with water, washed with brine, dried over magnesium sulfate and concentrated in vacuum. The residue was purified by column chromatography (silica 60, chloroform/ethyl acetate 3:1, Rf=0.25) to afford 755 mg of the title compound of the formula

1. customThe solution was degassed in vacuum 5×, tetrakis(triphenylphosphine) palladium(0) (901 mg)
2. additionwas added
3. temperatureAfter the reaction mixture was cooled to room temperature
4. customthe solid was removed by filtration
5. washthe filter cake was washed with ethyl acetate
6. additionWater was added to the filtrate
7. customthe layers were separated
8. extractionextracted with ethyl acetate
9. washThe combined organic layer was washed 3× with water
10. washwashed with brine
11. dry with materialdried over magnesium sulfate
12. concentrationconcentrated in vacuum
13. customThe residue was purified by column chromatography (silica 60, chloroform/ethyl acetate 3:1, Rf=0.25)

ORD record

ord-1ea1c1aeedc641c8a275d26b4fa30195

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08247431B2