1,4-Dioxane--water (1/1) → HCID 178519752, compound

HRID 2374161Notes

Reaction equation

HRID 2374161 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]1

Participants

3

Reactant 2

HCID 218864351,4-Dioxane--water (1/1)HCID 178428356HCID 178428356, compound

Product 1

HCID 178519752HCID 178519752, compound

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

  1. customsubjected to microwave irradiation (300 W, normal absorbance) at 180° C. for three 20 min interyals
  2. additionThe mixture was subsequently treated with satd
  3. customaq. NaHCO3 (25 ml) and water (25 ml) and the solids were removed by filtration through Celite
  4. washrinsing with DCM
  5. extractionThe filtrate was extracted with DCM (4×50 mL)
  6. dry with materialthe combined organic extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-c7164df1ca0d4e3cb01416dbd3f1de79
Source dataset
uspto-grants-2008_12
Patent number
US07462600B2

Reaction notes

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