Water → 5-(cyclohexylmethyl)-5-[4-(methylsulfonyl)phenyl]-5H-imidazo[2,1-a]isoindole

HRID 46177Notes

Reaction equation

HRID 46177 reaction equation
[CH:1]1([CH2:7][C:8]2([C:20]3[CH:25]=[CH:24][C:23]([S:26][CH3:27])=[CH:22][CH:21]=3)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]3=[N:17][CH:18]=[CH:19][N:9]23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH2:28].[OH:29]OS([O-])=O.[K+]>CO>[CH:1]1([CH2:7][C:8]2([C:20]3[CH:21]=[CH:22][C:23]([S:26]([CH3:27])(=[O:29])=[O:28])=[CH:24][CH:25]=3)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]3=[N:17][CH:18]=[CH:19][N:9]23)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 462052815-(cyclohexylmethyl)-5-[4-(methylthio)phenyl]-5H-imidazo[2,1-a]isoindole

Product 1

HCID 462052825-(cyclohexylmethyl)-5-[4-(methylsulfonyl)phenyl]-5H-imidazo[2,1-a]isoindole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 5-(cyclohexylmethyl)-5-[4-(methylthio)phenyl]-5H-imidazo[2,1-a]isoindole (38 mg) in MeOH (1 mL) was added water drop wise until the clear solution started to become turbid. Oxone (69 mg) was added at this time and stirred at room temperature 21 h. The reaction mixture was then diluted with MeOH, filtered and the filtrate was concentrated. Purification by reversed phase HPLC (21×100 mm Phenomenex Gemini, 15-85% MeCN/water containing 0.05% NH4OH over 20 min at 20 mL/min) afforded title compound as a white solid. HRMS. Found, 407.1802; calcd for (M+H)+, 407.1788. 1H NMR (500 MHz, CDCl3): δ 7.89-7.85 (m, 3 H); 7.45-7.39 (m, 1 H); 7.37 (d, J=1.28 Hz, 1 H); 7.32-7.26 (m, 3 H); 7.24 (d, J=8.00 Hz, 1 H); 6.99 (d, J=1.29 Hz, 1 H); 3.01 (s, 3 H); 2.60 (dd, J=14.41, 4.34 Hz, 1 H); 2.41 (dd, J=14.40, 4.00 Hz, 1 H); 1.54-1.38 (m, 3 H); 1.33-1.19 (m, 2 H); 1.10-0.73 (m, 7 H).

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated
  3. customPurification by reversed phase HPLC (21×100 mm Phenomenex Gemini, 15-85% MeCN/water containing 0.05% NH4OH over 20 min at 20 mL/min)

Sources & evidence

ORD record
ord-5e39091809924f63ba2995c029a389fc
Source dataset
uspto-grants-2013_09
Patent number
US08541595B2

Reaction notes

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