Potassium Carbonate → 4-(5-Bromopyridin-2-yl)piperidine-4-carbonitrile

1.0M Tetrahydrofuran-solution of sodium bis(trimethylsilyl)amide (19 ml) was added to 4-cyanopiperidine-1-carboxylic acid tert-butyl ester (3.23 g) at 0° C. and stirred for 50 minutes. A solution of 5-bromo-2-fluoropyridine (2.57 g) in tetrahydrofuran (5 ml) was added thereto and stirred at room temperature for 7.5 hours. An aqueous solution of potassium carbonate was added to the reaction solution and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. 2N Hydrochloric acid-ethanol solution (30 ml) was added to the residue and stirred for 4.5 hours. An aqueous solution of sodium bicarbonate was added to the reaction solution, extracted with ethyl acetate, and then with chloroform, washed with saturated brine dried over anhydrous sodium sulfate and concentrated in vacuo. The resulting solid was washed with isopropylether to give 4-(5-bromopyridin-2-yl)piperidine-4-carbonitrile (2.73 g) as a pale orange solid

1. stirringstirred at room temperature for 7.5 hours
2. extractionextracted with ethyl acetate
3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
4. concentrationconcentrated in vacuo
5. addition2N Hydrochloric acid-ethanol solution (30 ml) was added to the residue
6. stirringstirred for 4.5 hours
7. additionAn aqueous solution of sodium bicarbonate was added to the reaction solution
8. extractionextracted with ethyl acetate
9. washwith chloroform, washed with saturated brine
10. dry with materialdried over anhydrous sodium sulfate
11. concentrationconcentrated in vacuo
12. washThe resulting solid was washed with isopropylether

ORD record

ord-aebb5be7b4b347b3a48bc499ba1fcbcd

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09150555B2