Water → 5-Biphenyl-4-yl-6-fluoro-2-methanesulfonyl-1H-benzoimidazole

HRID 1960134Notes

Reaction equation

HRID 1960134 reaction equation
[O-:1][Mn](=O)(=O)=O.[K+].[C:7]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:12]=[CH:11][C:10]([C:13]2[C:23]([F:24])=[CH:22][C:16]3[NH:17][C:18]([S:20][CH3:21])=[N:19][C:15]=3[CH:14]=2)=[CH:9][CH:8]=1.[OH2:31]>C(O)(=O)C.CCOC(C)=O>[C:7]1([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:12]=[CH:11][C:10]([C:13]2[C:23]([F:24])=[CH:22][C:16]3[NH:17][C:18]([S:20]([CH3:21])(=[O:1])=[O:31])=[N:19][C:15]=3[CH:14]=2)=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 962WaterHCID 516875Potassium Permanganate2×HCID 673766005-Biphenyl-4-yl-6-fluoro-2-methylsulfanyl-1H-benzoimidazole

Product 1

HCID 674455365-Biphenyl-4-yl-6-fluoro-2-methanesulfonyl-1H-benzoimidazole

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To 32 mL of acetic acid was added compound 13-5 (2.34, 6.4 mmol) resulting in a suspension. In a separate flask KMnO4 (2.48 g, 15.7 mmol) was dissolved in 40 mL of H2O. The KMnO4 solution was then added to the solution of compound 13-5 in acetic acid and allowed to stir for 2 h at ambient temperature. The dark reaction mixture was diluted with EtOAc (200 mL) and washed three times with 150 mL portions of brine. The combined organic layers were dried over MgSO4, then filtered and concentrated in vacuo to give title compound 13-6 as a pale yellow solid.

Workup

  1. customresulting in a suspension
  2. customThe dark reaction mixture
  3. washwashed three times with 150 mL portions of brine
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-179018b4bcba4b45b073333a238a45a2
Source dataset
uspto-grants-2013_04
Patent number
US08410284B2

Reaction notes

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