Thionyl Chloride → HCID 319582, compound

Participants

Reaction Conditions

Reaction Steps

6-Chloropyridine-2,3-diamine (Example 23, Step 1) (150 mg, 1.045 mmol) was taken-up in dioxane (21.0 ml) under argon at room temperature. Thionyl chloride (686 μl, 9.40 mmol) was added dropwise over 15 minutes. The mixture was then stirred at 75° C. for 24 hours. The reaction was quenched with water and extracted three times with ethyl acetate. All organic layers were combined, dried over anhydrous magnesium sulfate, and concentrated. The resulting crude product was purified by silica gel chromatography (0-65% ethyl acetate/hexanes) to afford 5-chloro[1,2,5]thiadiazolo[3,4-b]pyridine. LRMS (APCI) calc'd for (C5H3ClN3S) [M+H]+, 172. found 172.

Provenance & Evidence