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

HRID 747200Notes

Reaction equation

HRID 747200 reaction equation
[N:1]([CH2:4][CH:5]1[O:9][N:8]=[C:7]([C:10]2[S:11][C:12]([Br:15])=[CH:13][CH:14]=2)[CH2:6]1)=[N+:2]=[N-:3].[CH:16]12CC(C=C1)C=[CH:17]2>O1CCOCC1>[Br:15][C:12]1[S:11][C:10]([C:7]2[CH2:6][CH:5]([CH2:4][N:1]3[CH:17]=[CH:16][N:3]=[N:2]3)[O:9][N:8]=2)=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 8473NorbornadieneHCID 179544855-Azidomethyl-3-(5-bromo-thien-2-yl)-4,5-dihydro-isoxazole

Product 1

HCID 597495131-[3-(5-Bromo-thien-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-thien-2-yl)-4,5-dihydro-isoxazole (500 mg, 1.74 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 (234 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-28f6b10ed7954500bbd05da45ca9fe1d
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

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