Nitronium tetrafluoroborate → HCID 117601096, compound

HRID 1773747Notes

Reaction equation

HRID 1773747 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([F:12])[C:9]([C:13]2[C:14]([CH3:19])=[N:15][O:16][C:17]=2[CH3:18])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].F[B-](F)(F)F.[O:25]=[N+:26]=[O:27]>C(O)(C(F)(F)F)=O>[NH2:1][C:2]1[C:11]([N+:26]([O-:27])=[O:25])=[C:10]([F:12])[C:9]([C:13]2[C:14]([CH3:19])=[N:15][O:16][C:17]=2[CH3:18])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 11073463Nitronium tetrafluoroborateHCID 117601064HCID 117601064, compound

Product 1

HCID 117601096HCID 117601096, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a mixture of methyl 2-amino-5-(3,5-dimethylisoxazol-4-yl)-4-fluorobenzoate (14 g, 53 mmol, 1 equiv.) and TFA (100 mL) is slowly added nitronium tetrafluoroborate (9.1 g, 68.9 mmol, 1.3 equiv.). After completion, the mixture was concentrated under reduced pressure. The residue was dissolved and then the residue was dissolved in EtOAc (200 ml) and washed with brine (30 ml×2). The organic solvent was evaporated. Methyl 2-amino-5-(3,5-dimethylisoxazol-4-yl)-4-fluoro-3-nitrobenzoate was used without further purification. 1H NMR (400 MHz, Chloroform-d) δ 6.92 (d, J=5.8 Hz, 1H), 4.24 (s, 4H), 4.07-3.85 (m, 5H), 2.46-2.34 (m, 4H), 2.31-2.22 (m, 5H).

Workup

  1. concentrationAfter completion, the mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved
  3. dissolutionthe residue was dissolved in EtOAc (200 ml)
  4. washwashed with brine (30 ml×2)
  5. customThe organic solvent was evaporated
  6. customMethyl 2-amino-5-(3,5-dimethylisoxazol-4-yl)-4-fluoro-3-nitrobenzoate was used without further purification

Sources & evidence

ORD record
ord-ddfc83294eff492cbee6a1454e96bd06
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

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