5-Azidomethyl-3-(5-bromo-pyridin-2-yl)-4,5-dihydro-isoxazole → N-[3-(5-Bromo-pyridin-2-yl)-4,5-dihydro-isoxazol-5-ylmethyl]-acetamide
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+]=[N-].[C:17]([OH:20])(=S)[CH3:18]>>[Br:16][C:13]1[CH:14]=[CH:15][C:10]([C:7]2[CH2:6][CH:5]([CH2:4][NH:1][C:17](=[O:20])[CH3:18])[O:9][N:8]=2)=[N:11][CH:12]=1Participants
3
Procedure
5-Azidomethyl-3-(5-bromo-pyridin-2-yl)-4,5-dihydro-isoxazole (3 g, 10.6 mmol) and thioacetic acid (10 ml) were combined and stirred for 52 hours. The reaction mixture was concentrated in vacuo and then ethyl acetate (20 ml) was added. The resulting precipitate was filtered and washed with ethyl acetate (2×20 ml) to give the desired product (1.8 g).
Workup
- concentrationThe reaction mixture was concentrated in vacuo
- additionethyl acetate (20 ml) was added
- filtration