3-Pyridinecarboxaldehyde → HCID 86634547, compound

Temperature

0 °C

2,2,6,6 Tetramethyl piperidine (1.97 ml, 11.6 mmol) is added dropwise to a solution o of n-Butyl lithium (6.87 ml, 11.0 mmol of 1.6 M solution in THF) in THF (40 ml) at −78° C., and the resulting solution stirred at this temperature for 5 minutes. The reaction mixture is allowed to warm to 0° C. and the reaction stirred at this temperature for 35 minutes. The reaction is cooled to −78° C., and 2-chloropyrazine (0.78 ml, 8.73 mmol) is added dropwise to form a red solution, which is stirred at −78° C. for 40 minutes. Pyridine-3-carbaldehyde (0.93 ml, 9.95 mmol) is added dropwise and stirred at −78° C. for 1 hour and 40 minutes. The reaction is quenched using 5M HCl (5 ml) at −78° C. and the reaction then allowed to warm slowly to room temperature. The pH is adjusted to 7 by the addition of sat. aq. NaHCO3 solution, and the product extracted into ethyl acetate (2×200 ml), dried (MgSO4) and the solvent removed in vacuo to afford a black oil which is purified using flash chromatography (SiO2, iso-hexane/EtOAc) to afford (3-chloro-pyrazin-2-yl)-pyridin-3-yl-methanol as a pale brown solid [M+H]+ 222.

1. stirringthe reaction stirred at this temperature for 35 minutes
2. temperatureThe reaction is cooled to −78° C.
3. customto form a red solution, which
4. stirringis stirred at −78° C. for 40 minutes
5. stirringstirred at −78° C. for 1 hour and 40 minutes
6. customThe reaction is quenched
7. customat −78° C.
8. customthe reaction
9. temperatureto warm slowly to room temperature
10. extractionthe product extracted into ethyl acetate (2×200 ml)
11. dry with materialdried (MgSO4)
12. customthe solvent removed in vacuo
13. customto afford a black oil which
14. customis purified

ORD record

ord-2de1e64cc587496b9e34385ba033aa27

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08846687B2