Potassium Permanganate → 2-cyclobutyl-1-(4-methanesulfonyl-phenyl)-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethanol

HRID 1515884Notes

Reaction equation

HRID 1515884 reaction equation
[CH:1]1([CH2:5][C:6]([C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:25])=[O:24])=[CH:19][CH:18]=2)([C:8]2[NH:16][C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[CH:9]=2)[OH:7])[CH2:4][CH2:3][CH2:2]1.[Mn]([O-])(=O)(=O)=[O:27].[K+]>CO.O>[CH:1]1([CH2:5][C:6]([C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:25])(=[O:27])=[O:24])=[CH:19][CH:18]=2)([C:8]2[NH:16][C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[CH:9]=2)[OH:7])[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 516875Potassium PermanganateHCID 672283422-cyclobutyl-1-(4-methanesulfinyl-phenyl)-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethanol

Product 1

HCID 583052492-cyclobutyl-1-(4-methanesulfonyl-phenyl)-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethanolYield 33%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-cyclobutyl-1-(4-methanesulfinyl-phenyl)-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethanol (94.2 mg, 0.266 mmol) in methanol (10 mL) at 0° C. was added a solution of potassium permanganate (42.0 mg, 0.266 mmol) in water (5 mL) dropwise. The mixture was stirred for 2 h at 0° C., extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, filtered through a short silical gel pad (QingDao silica gel, 200-300 mesh), and concentrated in vacuo. The residue was purified using a Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) to afford 2-cyclobutyl-1-(4-methanesulfonyl-phenyl)-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethanol (32.2 mg, 33%): LC/MS m/e calcd for C20H22N2O3S [M+H]+ 371.47, observed 371.2; 1H NMR (400 MHz, CD3OD) δ ppm 1.49 (m, 1H), 1.57-1.83 (m, 4H), 1.95 (m, 1H), 2.52 (m, 3H), 3.10 (s, 3H), 6.53 (s, 1H), 7.07 (dd, J=4.9, 7.8 Hz, 1H), 7.79 (d, J=8.7 Hz, 2H), 7.90 (d, J=8.7 Hz, 2H), 7.95 (dd, J=1.5 Hz, J=7.8 Hz, 1H), 7.95 (dd, J=1.5 Hz, J=4.9 Hz, 1H).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered through a short silical gel pad (QingDao silica gel, 200-300 mesh)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified

Sources & evidence

ORD record
ord-f112cf51543f4d6395406d507361ec94
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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