Selenium Dioxide → 6-chloro-3-morpholino-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbaldehyde

Participants

Reaction Steps

4-(6-Chloro-4-methyl-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)morpholine (Example 106, Step 1; 450.9 mg, 0.911 mmol) was dissolved in dioxane (10 mL) and selenium dioxide (303 mg, 2.73 mmol) was added. The reaction mixture was stirred at reflux over the weekend. The reaction was filtered over celite, rinsed with ethyl acetate, and concentrated in vacuo. The residue was diluted with DCM and filtered over celite. The filtrate was concentrated in vacuo while loading onto silica gel. Purification by flash chromatography (5-40% EtOAc/Hexanes) gave 6-chloro-3-morpholino-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbaldehyde. MS ESI calc'd. For C30H26ClN4O2 [M+H]+ 509. found 509.

Provenance & Evidence