Sodium Chloride → 5-Azidomethyl-3-(5-bromo-pyridin-2-yl)-4,5-dihydro-isoxazole

HRID 747193Notes

Reaction equation

HRID 747193 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:12][CH:11]([CH2:13]OS(C)(=O)=O)[O:10][N:9]=2)=[N:6][CH:7]=1.[N-:19]=[N+:20]=[N-:21].[Na+].[Cl-].[Na+]>CN(C)C=O>[N:19]([CH2:13][CH:11]1[O:10][N:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)[CH2:12]1)=[N+:20]=[N-:21]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 33557Sodium AzideHCID 59749444Methanesulfonic acid 3-(5-bromo-pyridin-2-yl)-4,5-dihydro-isoxazol-5-ylmethyl ester

Product 1

HCID 179544695-Azidomethyl-3-(5-bromo-pyridin-2-yl)-4,5-dihydro-isoxazoleYield 58.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

Methanesulfonic acid 3-(5-bromo-pyridin-2-yl)-4,5-dihydro-isoxazol-5-ylmethyl ester (30.5 g, 90.77 mmol) was added to dimethyl formamide (50 ml) followed by addition of sodium azide (11.8 g, 181.5 mmol). The mixture was heated to 75° C. for five hours and then added to aqueous sodium chloride (100 ml) followed by extraction with ethyl acetate (3×200 ml). The organic layers were combined, dried over sodium sulfate, and concentrated in vacuo to yield the desired product (15 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate (3×200 ml)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-61406d142970422e9faea61043c10f5b
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

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