Selenium Dioxide → 3-Bromo-5-(1,3-dioxoisoindolin-2-yl)picolinaldehyde

Participants

Reaction Conditions

Reaction Steps

To 2-(5-bromo-6-methylpyridin-3-yl)isoindoline-1,3-dione (30A, 1.5 g, 4.73 mmol) and selenium dioxide (682 mg, 6.15 mmol) was added 14 mL of DME. The reaction mixture was heated in a 130° C. heating bath for 20 hours. The reaction was repeated on identical scale 4×. The combined reaction mixtures were cooled and the solids filtered off. The filtrate was concentrated to afford 6 g of the title compound. 1H NMR (400 MHz, DMSO) δ 10.04 (s, 1H), 8.95 (d, J=1.9 Hz, 1H), 8.41 (d, J=1.7 Hz, 1H), 8.07-7.84 (m, 4H).

Provenance & Evidence