Potassium Permanganate → HCID 59437287, compound

HRID 244444Notes

Reaction equation

HRID 244444 reaction equation
[O:1]=[CH:2][CH2:3][N:4]1[CH:8]=[C:7]([C:9]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[N:19]=[CH:18]3)([OH:14])[C:10]([F:13])([F:12])[F:11])[CH:6]=[C:5]1[C:31]#[N:32].[O-:33][Mn](=O)(=O)=O.[K+]>CC(C)=O.O>[C:31]([C:5]1[N:4]([CH2:3][C:2]([OH:33])=[O:1])[CH:8]=[C:7]([C:9]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([C:24]2[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=2)[N:19]=[CH:18]3)([OH:14])[C:10]([F:12])([F:13])[F:11])[CH:6]=1)#[N:32]

Participants

4

Reactant 2

HCID 516875Potassium PermanganateHCID 59437244HCID 59437244, compound

Product 1

HCID 59437287HCID 59437287, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

To a solution of 1-(2-oxoethyl)-4-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-pyrrole-2-carbonitrile (208 mg, 0.47 mmol, 1 equiv.) in 12 mL of 3:1 acetone-water was added KMnO4 (78 mg, 0.49 mmol, 1.1 equiv.). After 18 hours, the mixture was filtered through CELITE® filter aid and the filter cake washed with acetone. The filtrate was evaporated and the aqueous was diluted with water and EtOAc. The mixture was diluted with saturated aqueous ammonium chloride and extracted with EtOAc. The combined organic layers were dried, filtered, and concentrated in vacuo to provide 197 mg (91%) of (2-cyano-4-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}pyrrol-1-yl)acetic acid which was used without further purification.

Workup

  1. filtrationthe mixture was filtered through CELITE®
  2. filtrationfilter aid
  3. washthe filter cake washed with acetone
  4. customThe filtrate was evaporated
  5. additionthe aqueous was diluted with water and EtOAc
  6. additionThe mixture was diluted with saturated aqueous ammonium chloride
  7. extractionextracted with EtOAc
  8. customThe combined organic layers were dried
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cc687da176a049aeb2c48228f78afe2b
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

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