1,4-Dioxane--water (1/1) → HCID 178519752, compound
Reaction equation
[CH:1]1([C:4]2[NH:13][C:7]3=[N:8][CH:9]=[CH:10][C:11]([CH3:12])=[C:6]3[N:5]=2)[CH2:3][CH2:2]1.[O:14]1CCOCC1.O>>[CH:1]1([C:4]2[NH:13][C:7]3=[N:8][CH:9]=[CH:10][C:11]([CH:12]=[O:14])=[C:6]3[N:5]=2)[CH2:3][CH2:2]1Participants
3
Procedure
2-Cyclopropyl-7-methyl-3H-imidazo[4,5-b]pyridine (100 mg, 0.58 mmol; from EP0420237 A1) was treated with SeO2 (160 mg, 1.44 mmol) in 6 ml of dioxane:water (4:1) and subjected to microwave irradiation (300 W, normal absorbance) at 180° C. for three 20 min interyals. The mixture was subsequently treated with satd. aq. NaHCO3 (25 ml) and water (25 ml) and the solids were removed by filtration through Celite, rinsing with DCM. The filtrate was extracted with DCM (4×50 mL) and the combined organic extracts were dried (Na2SO4), filtered, and concentrated to dryness to yield the crude title compound. MS (ESI+) for m/z 188 (M+H)+.
Workup
- customsubjected to microwave irradiation (300 W, normal absorbance) at 180° C. for three 20 min interyals
- additionThe mixture was subsequently treated with satd