m-Chloroperbenzoic acid → HCID 69309652, compound

HRID 1947027Notes

Reaction equation

HRID 1947027 reaction equation
[F:1][C:2]([F:26])([F:25])[CH2:3][CH:4]([OH:24])[CH2:5][O:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][N:11]2[C:16]1[CH:21]=[CH:20][N:19]=[C:18]([S:22][CH3:23])[N:17]=1.C1C=C(Cl)C=C(C(OO)=[O:35])C=1>C(Cl)(Cl)Cl>[F:26][C:2]([F:25])([F:1])[CH2:3][CH:4]([OH:24])[CH2:5][O:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][N:11]2[C:16]1[CH:21]=[CH:20][N:19]=[C:18]([S:22]([CH3:23])=[O:35])[N:17]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 69309492HCID 69309492, compound

Product 1

HCID 69309652HCID 69309652, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4,4,4-Trifluoro-1-[1-(2-methylsulfanyl-pyrimidin-4-yl)-1H-indol-4-yloxy]-butan-2-ol (1.5 g) in CHCl3 (200 mL) at 0° C. was stirred for 3 h with MCPBA (0.962 g) at 0° C., then quenched with 10% aqueous sodium thiosulfate. The organic layer was separated, washed with saturated NaHCO3 and brine, dried over sodium sulfate, filtered, concentrated in vacuo and purified on a column with 100% DCM to 15% MeOH/DCM (product eluting at 5% MeOH) to yield 4,4,4-trifluoro-1-[1-(2-methylsulfinyl-pyrimidin-4-yl)-1H-indol-4-yloxy]-butan-2-ol (˜1.4 g).

Workup

  1. customquenched with 10% aqueous sodium thiosulfate
  2. customThe organic layer was separated
  3. washwashed with saturated NaHCO3 and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified on a column with 100% DCM to 15% MeOH/DCM (product eluting at 5% MeOH)

Sources & evidence

ORD record
ord-2062d4eea6d047d78be53d2beb23ae1a
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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