Trifluoroacetic anhydride → 4-Cyano-2-(1-ethyl-1H-pyrazol-4-yl)-3-(methoxycarbonyl)pyridine 1-oxide

HRID 516053Notes

Reaction equation

HRID 516053 reaction equation
[C:1]([C:3]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([C:13]2[CH:14]=[N:15][N:16]([CH2:18][CH3:19])[CH:17]=2)[N:6]=[CH:5][CH:4]=1)#[N:2].OO.NC(N)=[O:24].FC(F)(F)C(OC(=O)C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(#N)C.C(Cl)(Cl)Cl>[C:1]([C:3]1[CH:4]=[CH:5][N+:6]([O-:24])=[C:7]([C:13]2[CH:14]=[N:15][N:16]([CH2:18][CH3:19])[CH:17]=2)[C:8]=1[C:9]([O:11][CH3:12])=[O:10])#[N:2]

Participants

7

Reactant 4

HCID 9845Trifluoroacetic anhydrideHCID 31294Carbamide PeroxideHCID 516892Sodium BicarbonateHCID 58317527Methyl 4-cyano-2-(1-ethyl-1H-pyrazol-4-yl)nicotinate

Product 1

HCID 672385264-Cyano-2-(1-ethyl-1H-pyrazol-4-yl)-3-(methoxycarbonyl)pyridine 1-oxide

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

To a mixture of methyl 4-cyano-2-(1-ethyl-1H-pyrazol-4-yl)nicotinate (207 mg, 0.808 mmol) in ACN (2 mL) was added urea hydrogen peroxide (380 mg, 4.04 mmol) and trifluoroacetic anhydride (0.456 mL, 3.23 mmol) at 0° C. The resulting mixture was stirred at RT overnight. Next, saturated aq NaHCO3 solution and chloroform were added. The aqueous phase was extracted with chloroform (3×200 mL). The organic layers were combined and washed with brine, dried over MgSO4, and evaporated to give the title compound which was used without further purification (210 mg, 95%). [M+H] calc'd for C13H12N4O3, 273.5; found, 273.5.

Workup

  1. extractionThe aqueous phase was extracted with chloroform (3×200 mL)
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-cfb05b19f78942bea2106dda301ffbab
Source dataset
uspto-grants-2015_08
Patent number
US09108970B2

Reaction notes

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