Azobisisobutyronitrile → 5-((1H-1,2,4-Triazol-1-yl)methyl)-3-bromo-2-(difluoromethoxy)pyridine

HRID 2271460Notes

Reaction equation

[Br:1][C:2]1[C:3]([O:10][CH:11]([F:13])[F:12])=[N:4][CH:5]=[C:6]([CH2:8]Br)[CH:7]=1.BrC1[C:16](OC(F)F)=[N:17][CH:18]=C(C)C=1.BrN1C(=O)CCC1=O.[N:34](C(C)(C)C#N)=[N:35]C(C)(C)C#N>C(Cl)(Cl)(Cl)Cl.O>[N:34]1([CH2:8][C:6]2[CH:7]=[C:2]([Br:1])[C:3]([O:10][CH:11]([F:13])[F:12])=[N:4][CH:5]=2)[CH:18]=[N:17][CH:16]=[N:35]1

Participants

Conditions

Temperature: 80 °C

Procedure

3-Bromo-5-(bromomethyl)-2-(difluoromethoxy)pyridine. To a solution of 3-bromo-2-(difluoromethoxy)-5-methylpyridine (0.50 g, 2.1 mmol) in carbon tetrachloride (13 mL), was added 1-bromopyrrolidine-2,5-dione (0.521 g, 2.93 mmol), and azobisisobutyronitrile (44 mg, 0.26 mmol). The reaction mixture was stirred at 80° C. for 8 h. The reaction mixture was diluted with water and extracted with DCM. The combined organic layers were dried (Na2SO4), and the solvent was removed under reduced pressure. Purification (FCC, SiO2, 10-90%, EtOAc/hexanes) afforded the title compound (400 mg, 60%). [M+H]=317.88.

Workup

extractionextracted with DCM
dry with materialThe combined organic layers were dried (Na2SO4)
customthe solvent was removed under reduced pressure
customPurification (FCC, SiO2, 10-90%, EtOAc/hexanes)

Sources & evidence

ORD record: ord-b19f57ee78bd4c37afdb0ac8c09ada19
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120770B2

Reaction notes

Loading…