Di-tert-butyl azodicarboxylate → HCID 67212506, compound

HRID 1671347Notes

Reaction equation

HRID 1671347 reaction equation
Br[C:2]1[C:3]([CH3:19])=[N:4][N:5]2[C:9]([C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=3[Cl:17])=[C:8]([CH3:18])[O:7][C:6]=12.C([Li])CCC.[N:25]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[N:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28]>C1COCC1>[C:37]([O:36][C:34]([NH:25][N:26]([C:2]1[C:3]([CH3:19])=[N:4][N:5]2[C:9]([C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=3[Cl:17])=[C:8]([CH3:18])[O:7][C:6]=12)[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[O:35])([CH3:40])([CH3:39])[CH3:38]

Participants

5

Reactant 3

HCID 97268Di-tert-butyl azodicarboxylateHCID 67212702HCID 67212702, compoundHCID 178418339Butyllithium

Product 1

HCID 67212506HCID 67212506, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a stirring solution of 7-bromo-3-(2,4-dichloro-phenyl)-2,6-dimethyl-pyrazolo[5,1-b]oxazole (710 mg, 1.972 mmol) in THF (15.5 ml) under N2 at −78° C. is added n-butyllithium (0.789 ml, 1.972 mmol) dropwise; the temperature is maintained below −70° C. for the addition and then the reaction mixture is stirred for 5 mins at −78° C. before the addition of di-tert-butyl azodicarboxylate (545 mg, 2.366 mmol) in THF (1.5 ml); the temperature is maintained below −60° C. for the period of the addition. After stirring at −78° C. for 30 mins, the reaction is quenched with sat. ammonium chloride solution and allowed to warm to RT. Ammonium chloride solution (sat.) is added and the mixture is extracted with EtOAc (2×100 ml). The combined organics extracts are washed with brine, dried over MgSO4 and concentrated in vacuo. The crude product is purified ISCO chromatography eluting (0 to 100%) EtOAci iso-hexane on a 40 g SiO2 cartridge to give the title compound as an orange solid; MS: m/z 511.22 [M+H]+

Workup

  1. temperaturethe temperature is maintained below −70° C. for the addition
  2. temperaturethe temperature is maintained below −60° C. for the period of the addition
  3. customthe reaction is quenched with sat. ammonium chloride solution
  4. temperatureto warm to RT
  5. additionAmmonium chloride solution (sat.) is added
  6. extractionthe mixture is extracted with EtOAc (2×100 ml)
  7. washThe combined organics extracts are washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customThe crude product is purified ISCO chromatography
  11. washeluting (0 to 100%) EtOAci iso-hexane on a 40 g SiO2 cartridge

Sources & evidence

ORD record
ord-4f62b8207caa43c69c4b48c76a52ad8b
Source dataset
uspto-grants-2011_08
Patent number
US07994203B2

Reaction notes

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