Norbornadiene → 1-[3-(5-Bromo-pyridin-2-yl)-4,5-dihydro-isoxazol-5-ylmethyl]-1H-1,2,3-triazole

HRID 747195Notes

Reaction equation

HRID 747195 reaction equation
[N:1]([CH2:4][CH:5]1[O:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][N:11]=2)[CH2:6]1)=[N+:2]=[N-:3].[CH:17]12CC(C=C1)C=[CH:18]2>O1CCOCC1>[Br:16][C:13]1[CH:14]=[CH:15][C:10]([C:7]2[CH2:6][CH:5]([CH2:4][N:1]3[CH:18]=[CH:17][N:3]=[N:2]3)[O:9][N:8]=2)=[N:11][CH:12]=1

Participants

4

Reactant 2

HCID 8473NorbornadieneHCID 179544695-Azidomethyl-3-(5-bromo-pyridin-2-yl)-4,5-dihydro-isoxazole

Product 1

HCID 597494261-[3-(5-Bromo-pyridin-2-yl)-4,5-dihydro-isoxazol-5-ylmethyl]-1H-1,2,3-triazole

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5-Azidomethyl-3-(5-bromo-pyridin-2-yl)-4,5-dihydro-isoxazole (1 g, 3.5 mmol) and bicyclo[2.2.1]hepta-2,5-diene (1 ml) were combined with dioxane (2 ml) and subjected to microwave radiation in a Smith Personal Synthesizer for 900 seconds at 125° C. The reaction mixture was concentrated in vacuo and ethyl acetate (5 ml) was added. The precipitate was filtered and washed with ethyl acetate (2×5 ml) to give the desired product (417 mg).

Workup

  1. customfor 900 seconds
  2. customat 125° C
  3. concentrationThe reaction mixture was concentrated in vacuo and ethyl acetate (5 ml)
  4. additionwas added
  5. filtrationThe precipitate was filtered
  6. washwashed with ethyl acetate (2×5 ml)

Sources & evidence

ORD record
ord-72ead158849d431dbe2fa0902e8a97d2
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

Loading…