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

HRID 747194Notes

Reaction equation

HRID 747194 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]=1

Participants

3

Reactant 2

HCID 179544695-Azidomethyl-3-(5-bromo-pyridin-2-yl)-4,5-dihydro-isoxazoleHCID 178418634HCID 178418634, compound

Product 1

HCID 59749491N-[3-(5-Bromo-pyridin-2-yl)-4,5-dihydro-isoxazol-5-ylmethyl]-acetamide

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

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionethyl acetate (20 ml) was added
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with ethyl acetate (2×20 ml)

Sources & evidence

ORD record
ord-7cbdd22013e542f3a185b3fa8aec6a5e
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

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