Selenium Dioxide → HCID 86674200, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:5]([CH3:8])=[N:6][CH:7]=1.[Se](=O)=[O:15]>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:5]([CH:8]=[O:15])=[N:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 180 °C
Procedure
To each of 106 separate 20-mL microwave vials, add: ethyl 5-bromo-2-methylpyridine-3-carboxylate (5 g, 20.48 mmol, 1.0 equiv), selenium dioxide (2.98 g, 26.63 mmol, 1.3 equiv), and 1,4-dioxane (13 mL). Heat the vessels to 180° C. for 20 min with microwave irradiation. Combine the contents of the reaction vessels; filter through a pad of silica gel (2 kg); and rinse the pad with DCM (3 L). Concentrate the combined filtrates under reduced pressure. Split the material into two equally-sized batches, and pass each through a pad of silica gel (2 kg) eluting with DCM. Concentrate the filtrate under reduced pressure to furnish the title compound as a yellow or pale orange solid (473 g, 93.2% yield). MS (m/z) (79Br/81Br) 258/260 (M+1).