(5-Bromo-6-methoxypyridin-2-yl)methanol → 5-Bromo-6-methoxypicolinaldehyde
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:10][OH:11])=[N:6][C:7]=1[O:8][CH3:9]>C(Cl)Cl.O=[Mn]=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:10]=[O:11])=[N:6][C:7]=1[O:8][CH3:9]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
(5-Bromo-6-methoxypyridin-2-yl)methanol of preparation 77 (92 mg, 0.42 mmol) was dissolved in DCM (5 ml). MnO2 (477 mg, 5.49 mmol) was added. The reaction was stirred under nitrogen at room temperature for overnight. LCMS showed ˜30% of the starting material remained, and the reaction continued for another 5 hr at which time ˜15% of the starting material remained by LCMS. The reaction mixture was filtered and the filtrate was evaporated to dryness in vacuo. A brownish solid was obtained (69 mg) which was used in the next step without further purification.