Sulfuric Acid → HCID 178518073, compound

HRID 593759Notes

Reaction equation

HRID 593759 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:13]2=[N:14][CH:15]=[CH:16][C:17]([C:18]3[CH:19]=[N:20][CH:21]=[N:22][CH:23]=3)=[C:12]2[O:11][N:10]=1.C(OO)(=[O:26])C.S(=O)(=O)(O)O.[OH-].[Na+]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:13]2=[N:14][CH:15]=[CH:16][C:17]([C:18]3[C:23]([OH:26])=[N:22][CH:21]=[N:20][CH:19]=3)=[C:12]2[O:11][N:10]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6585Peracetic AcidHCID 14798Sodium HydroxideHCID 867304153-(2-Chloro-4-fluorophenyl)-7-(pyrimidin-5-yl)isoxazolo[4,5-b]pyridine

Product 1

HCID 178518073HCID 178518073, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a vial charged with 3-(2-chloro-4-fluorophenyl)-7-(pyrimidin-5-yl) isoxazolo[4,5-b]pyridine (4.8 mg, 0.015 mmol) in acetone (Volume: 100 μl) were added peroxyacetic acid (6.18 μl, 0.029 mmol) and sulfuric acid (1.632 μl, 0.029 mmol). The reaction mixture was refluxed for 75 min, and then allowed to cool to room temperature. The reaction mixture was neutralized with 4 M NaOH and extracted with CH2Cl2 (5×). The organic phases were combined, dried over Na2SO4, filtered, and concentrated to afford the title compound as a yellow residue (5.0 mg, 99%). ESI MS (M+H)+=343.0.

Workup

  1. temperatureThe reaction mixture was refluxed for 75 min
  2. extractionextracted with CH2Cl2 (5×)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ac01340c31f044acab44244512db8470
Source dataset
uspto-grants-2016_01
Patent number
US09242967B2

Reaction notes

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