Bromide ion → 2-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-(3-nitro-pyrazol-1-ylmethyl)-oxazole

HRID 2065059Notes

Reaction equation

HRID 2065059 reaction equation
N#N.[C:3]([Si:7]([CH3:19])([CH3:18])[O:8][CH:9]([C:11]1[O:12][C:13]([CH2:16]Cl)=[CH:14][N:15]=1)[CH3:10])([CH3:6])([CH3:5])[CH3:4].[N+:20]([C:23]1[NH:27][N:26]=[CH:25][CH:24]=1)([O-:22])=[O:21].[Br-].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[C:3]([Si:7]([CH3:19])([CH3:18])[O:8][CH:9]([C:11]1[O:12][C:13]([CH2:16][N:26]2[CH:25]=[CH:24][C:23]([N+:20]([O-:22])=[O:21])=[N:27]2)=[CH:14][N:15]=1)[CH3:10])([CH3:6])([CH3:5])[CH3:4]

Participants

7

Reactant 5

HCID 259Bromide ionHCID 947NitrogenHCID 11430Potassium CarbonateHCID 1234193-NitropyrazoleHCID 66821221HCID 66821221, compound

Product 1

HCID 669285532-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-(3-nitro-pyrazol-1-ylmethyl)-oxazole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-chloromethyl-oxazole (243 mg, 0.88 mmol), 5-nitro-1H-pyrazole (100 mg, 0.88 mmol) and TBA bromide (57 mg, 0.18 mmol) in acetone (2.0 mL) was treated with K2CO3 (365 mg, 2.64 mmol) and the reaction mixture was stirred at rt until completion. The solvent was removed under reduced pressure and water (10 mL) followed by EA (10 mL) were added. The aq. layer was extracted with EA (10 mL) and the combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (6:4 hept-EA) gave the title compound as a yellow oil. TLC: rf (6:4 hept-EA)=0.20. LC-MS-conditions 01: tR=1.09 min, [M+H]+=353.02.

Workup

  1. customThe solvent was removed under reduced pressure and water (10 mL)
  2. additionwere added
  3. extractionThe aq. layer was extracted with EA (10 mL)
  4. dry with materialextracts were dried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customPurification of the residue by FC (6:4 hept-EA)

Sources & evidence

ORD record
ord-0431e0b073bf449a9dd766990ade8de8
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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