Potassium Permanganate → HCID 24957618, compound

HRID 244431Notes

Reaction equation

HRID 244431 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Br:13])[CH:11]=2)[C:6]([C:14]([C:20]2[CH:21]=[C:22]3[C:26](=[CH:27][CH:28]=2)[N:25]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[N:24]=[CH:23]3)([OH:19])[C:15]([F:18])([F:17])[F:16])=[CH:5]1)C=C.[O-][Mn](=O)(=O)=O.[K+].[CH3:42][C:43]([CH3:45])=[O:44].[OH2:46]>>[Br:13][C:10]1[CH:11]=[C:12]2[C:7]([C:6]([C:14]([C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[N:25]([C:29]3[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=3)[N:24]=[CH:23]4)([OH:19])[C:15]([F:17])([F:16])[F:18])=[CH:5][N:4]2[CH2:42][CH:43]([OH:44])[CH2:45][OH:46])=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 516875Potassium PermanganateHCID 18366337Propan-2-one--water (1/1)2×HCID 24957617HCID 24957617, compound

Product 1

HCID 24957618HCID 24957618, compoundYield 23%

Procedure

To a chilled (0° C.) solution of 0.3 g (0.5 mmol) 1-(1-allyl-6-bromo-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol in acetone-H2O (3:1) was added 93.2 mg (0.6 mmol) of KMnO4 in 5 mL of a 3:1 mixture of acetone-H2O dropwise. After 2 hours, the reaction was filtered and the solvent was concentrated in vacuo. The residue was diluted with water and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and the solvent was concentrated in vacuo. The residue was purified by HPLC (5-100% CH3CN-water buffered with TFA). The material from the column was concentrated, in vacuo to remove the acetonitrile. The aqueous layer was made basic and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated in vacuo to afford 60 mg (23%) of the title compound. MS m/z 579.35 (MH+).

Workup

  1. filtrationthe reaction was filtered
  2. concentrationthe solvent was concentrated in vacuo
  3. additionThe residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationthe solvent was concentrated in vacuo
  8. customThe residue was purified by HPLC (5-100% CH3CN-water buffered with TFA)
  9. concentrationThe material from the column was concentrated, in vacuo
  10. customto remove the acetonitrile
  11. extractionextracted with ethyl acetate
  12. dry with materialThe combined organic layers were dried over sodium sulfate
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-198ab31c8a5d4d678aff9b3a9752fd79
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

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