Bromide ion → HCID 131730014, compound

HRID 2065086Notes

Reaction equation

HRID 2065086 reaction equation
N#N.[C:3]([SiH2:7][O:8][C:9]([CH3:22])([CH3:21])[C:10]1[O:11][CH:12]=[C:13]([CH2:15]OS(C)(=O)=O)[N:14]=1)([CH3:6])([CH3:5])[CH3:4].[N+:23]([C:26]1[CH:27]=[N:28][NH:29][CH:30]=1)([O-:25])=[O:24].[Br-].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[C:3]([SiH2:7][O:8][C:9]([CH3:22])([CH3:21])[C:10]1[O:11][CH:12]=[C:13]([CH2:15][N:28]2[CH:27]=[C:26]([N+:23]([O-:25])=[O:24])[CH:30]=[N:29]2)[N:14]=1)([CH3:6])([CH3:5])[CH3:4]

Participants

7

Reactant 5

HCID 259Bromide ionHCID 947NitrogenHCID 11430Potassium CarbonateHCID 163764-nitro-1H-pyrazoleHCID 131730013HCID 131730013, compound

Product 1

HCID 131730014HCID 131730014, compound

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 methanesulfonic acid 2-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-4-ylmethyl ester (430 mg, 1.33 mmol), 4-nitro-1H-pyrazole (172 mg, 1.33 mmol) and TBA bromide (86 mg, 0.26 mmol) in acetone (15.0 mL) was treated with K2CO3 (935 mg, 6.69 mmol) and the reaction mixture was stirred at rt until completion. The solvent was removed under reduced pressure and water (10 mL) and EA (10 mL) were added. The aq. layer was extracted with EA (10 mL) and the combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (1:0 to 17:3 hept-EA) gave the title compound as a pale yellow solid. TLC: rf (1:1 hept-EA)=0.46. LC-MS-conditions 02: tR=1.09 min; [M+H]+=339.44.

Workup

  1. customThe solvent was removed under reduced pressure and water (10 mL) and EA (10 mL)
  2. additionwere added
  3. extractionThe aq. layer was extracted with EA (10 mL)
  4. dry with materialextracts were dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customPurification of the residue by FC (1:0 to 17:3 hept-EA)

Sources & evidence

ORD record
ord-10b9d0689409463d97491c690593e356
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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