Pyridine → HCID 68259684, compound

Temperature

25 °C

To a solution of 5-bromo-pyridine-2,3-dicarboxylic acid 2-isopropyl ester (630 mg, 2.187 mmol) in pyridine (8 ml) at 0° C. was added methane sulfonyl chloride (0.34 ml, 4.37 mmol, 2 equiv.) and the reaction mixture was stirred for 1 hour at 25° C. Then NH3 gas was purged in to reaction mixture at 0° C. and stirred at 25° C. for 30 minutes. The excess NH3 was evaporated off in vacuo. The reaction mixture was cooled to 0° C., a fresh lot of methane sulfonyl chloride (1.35 ml, 17.49 mmol, 8 equiv.) was added drop wise to the mixture and stirring was continued at 25° C. for another 16 hours. The reaction mixture was quenched with saturated aqueous NaHCO3 solution (20 ml) and extracted with EtOAc (2×40 ml). The combined organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure to dryness. The resulting crude material was purified by column chromatography over normal silica gel (10% EtOAc in hexane) to give 5-bromo-3-cyano-pyridine-2-carboxylic acid isopropyl ester (320 mg, 54%) as yellow oil.

1. customThen NH3 gas was purged in to reaction mixture at 0° C.
2. stirringstirred at 25° C. for 30 minutes
3. customThe excess NH3 was evaporated off in vacuo
4. temperatureThe reaction mixture was cooled to 0° C.
5. stirringstirring
6. waitwas continued at 25° C. for another 16 hours
7. customThe reaction mixture was quenched with saturated aqueous NaHCO3 solution (20 ml)
8. extractionextracted with EtOAc (2×40 ml)
9. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
10. customevaporated under reduced pressure to dryness
11. customThe resulting crude material was purified by column chromatography over normal silica gel (10% EtOAc in hexane)

ORD record

ord-428db6bf0b7843b38ed7e9c00fc3ae1d

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772300B2