Sodium Azide → HCID 58128600, compound

HRID 1798816Notes

Reaction equation

HRID 1798816 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[N:6][CH:7]=1.[N-:18]=[N+:19]=[N-:20].[Na+].[Na].O=C1O[C@H]([C@H](CO)O)C(O)=C1O.CN(C)CCN>[Cu]I>[N:18]([C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[N:6][CH:7]=1)=[N+:19]=[N-:20]

Participants

6

Reactant 4

HCID 33557Sodium AzideHCID 66053N,N-DimethylethylenediamineHCID 58128526HCID 58128526, compoundHCID 66586226sodium L-ascorbic acid

Product 1

HCID 58128600HCID 58128600, compound

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
100 °C

Procedure

5-Iodo-2-(4′-methoxybenzyloxy)pyridine from step 1 of this example (682 mg, 2.0 mmol), sodium azide (260 mg, 4.00 mmol), copper (1) iodide (38.1 mg, 0.200 mmol) and L-ascorbic acid sodium salt (19.81 mg, 0.100 mmol) were added to a sealable high pressure vessel. The vessel was evacuated and purged with nitrogen, then ethanol (2.75 ml) and water (1.25 ml) were added. N,N-dimethylethylenediamine (31.9 μl, 0.300 mmol) was then added via microliter syringe. The top was sealed and the reaction heated to 100° C. A safety shield was placed in front of the reaction as a precaution. After 90 minutes, the reaction was cooled to room temperature. Reaction was judged to be complete by TLC, so the reaction was partitioned between ethyl acetate and water. The aqueous was extracted again with ethyl acetate, and the combined organics washed again with water. The organic layer was dried over sodium sulfate, filtered and evaporated to give the crude product. The material was purified by column chromatography on a Biotage 40 g SiO2 column, eluting with 5-25% ethyl acetate/heptane to give the title compound as a light tan solid.

Workup

  1. customThe vessel was evacuated
  2. custompurged with nitrogen
  3. additionethanol (2.75 ml) and water (1.25 ml) were added
  4. customThe top was sealed
  5. customA safety shield was placed in front of the reaction as a precaution
  6. temperaturethe reaction was cooled to room temperature
  7. customReaction
  8. customwas partitioned between ethyl acetate and water
  9. extractionThe aqueous was extracted again with ethyl acetate
  10. washthe combined organics washed again with water
  11. dry with materialThe organic layer was dried over sodium sulfate
  12. filtrationfiltered
  13. customevaporated
  14. customto give the crude product
  15. customThe material was purified by column chromatography on a Biotage 40 g SiO2 column
  16. washeluting with 5-25% ethyl acetate/heptane

Sources & evidence

ORD record
ord-41471366e8a046729a7cf7fdd5ab2619
Source dataset
uspto-grants-2013_01
Patent number
US08343990B2

Reaction notes

Loading…