Iodine → HCID 59334570, compound

Temperature

-78 °C

To a solution of 2-methyl[1,2,4]triazolo[1,5-a]pyridine (63.2 g, 475 mmol) in tetrahydrofuran (1.37 L) was added dropwise 2.5 M n-butyllithium/hexane solution (5.62 mL, 8.99 mmol) at −78° C. and the mixture was stirred at −78° C. for 30 min. A solution of iodine (181 g, 712 mmol) in tetrahydrofuran (1.00 L) was added, and the mixture was stirred at −78° C. for 30 min, and at room temperature for 1 hr. Water (500 mL) was added to the reaction solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/2) to give the title compound (45.0 g, yield 37%).

1. stirringthe mixture was stirred at −78° C. for 30 min
2. waitat room temperature for 1 hr
3. extractionthe mixture was extracted with ethyl acetate
4. dry with materialThe extract was dried over anhydrous sodium sulfate
5. customthe solvent was evaporated under reduced pressure
6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/2)

ORD record

ord-6cb0b18948b8496086ef34abd89603da

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08110585B2