Hydrogen Peroxide → HCID 68003850, compound

HRID 1621272Notes

Reaction equation

HRID 1621272 reaction equation
F[C:2]1[CH:10]=[C:9](F)[CH:8]=[C:7]2[C:3]=1[C:4]([S:12][CH2:13][C:14]([NH:16][C:17]1[CH:21]=[C:20]([CH3:22])[O:19][N:18]=1)=[O:15])=[CH:5][NH:6]2.[OH:23]O>C(O)(C(F)(F)F)C(F)(F)F>[NH:6]1[C:7]2[C:3](=[CH:2][CH:10]=[CH:9][CH:8]=2)[C:4]([S:12]([CH2:13][C:14]([NH:16][C:17]2[CH:21]=[C:20]([CH3:22])[O:19][N:18]=2)=[O:15])=[O:23])=[CH:5]1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 68003849HCID 68003849, compound

Product 1

HCID 68003850HCID 68003850, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 135291,1,1,3,3,3-Hexafluoro-2-propanolSolvent

Procedure

2-((4,6-difluoro-1H-indol-3-yl)thio)-N-(5-methylisoxazol-3-yl)acetamide (100 mg, 0.348 mmol) from Step C was dissolved in hexafluoro-2-propanol (500 μL) and hydrogen peroxide (30% by weight, 88.0 μL, 0.696 mmol). The mixture was stirred at ambient temperature for 2 hours. The reaction was quenched with saturated aqueous sodium sulfite (500 μL) and extracted with ethyl acetate (3×1 mL). The organics were combined, dried over magnesium sulfate, and concentrated in vacuo to give a residue which was purified on a silica gel column (0-100% ethyl acetate:hexanes over 19 min) to yield the desired product (79.0 mg, 0.174 mmol, 75% yield). LCMS>99% at 220 nm, RT=1.00 min, m/z=304 (M+1).

Workup

  1. customThe reaction was quenched with saturated aqueous sodium sulfite (500 μL)
  2. extractionextracted with ethyl acetate (3×1 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a residue which
  6. customwas purified on a silica gel column (0-100% ethyl acetate:hexanes over 19 min)

Sources & evidence

ORD record
ord-57f24817e6ca4c3cbe1a815f321eecf4
Source dataset
uspto-grants-2014_07
Patent number
US08772509B2

Reaction notes

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