Sodium Azide → HCID 57528490, compound

HRID 1453820Notes

Reaction equation

HRID 1453820 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:21]([O:23][CH3:24])=[O:22])=[N:11][N:12]([CH2:18][CH2:19]Br)[C:13]=1[C:14]([O:16][CH3:17])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:25]=[N+:26]=[N-:27].[Na+]>CN(C=O)C>[N:25]([CH2:19][CH2:18][N:12]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:10]([C:21]([O:23][CH3:24])=[O:22])=[N:11]1)=[N+:26]=[N-:27]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 57528492Dimethyl 4-benzyloxy-1-(2-bromoethyl)-1H-pyrazole-3,5-dicarboxylate

Product 1

HCID 57528490HCID 57528490, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of dimethyl 4-benzyloxy-1-(2-bromoethyl)-1H-pyrazole-3,5-dicarboxylate (1.0 g, 2.52 mmol) in DMF was added sodium azide. The reaction mixture was stirred at 40° C. overnight and quenched with water (100 mL). The mixture was extracted with EtOAc four times, and the organic extracts were washed with brine, dried over Na2SO4, and concentrated in vacuo. The resulting residue was purified by flash chromatography on silica gel using 0-30% EtOAc/hexanes gradient elution. Collection and concentration of the appropriate fractions afforded the title compound as a white solid. ES MS (M+1)=360.

Workup

  1. customquenched with water (100 mL)
  2. extractionThe mixture was extracted with EtOAc four times
  3. washthe organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by flash chromatography on silica gel using 0-30% EtOAc/hexanes gradient elution
  7. customCollection and concentration of the appropriate fractions

Sources & evidence

ORD record
ord-ad6f685014124c448770a8d313256d2d
Source dataset
uspto-grants-2009_01
Patent number
US07476666B2

Reaction notes

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