Potassium Hydroxide → 2-(5,6-dihydro-2H-4-pyranyl)-5-methanesulfonylindole

HRID 1432238Notes

Reaction equation

HRID 1432238 reaction equation
[O:1]1[CH2:6][CH2:5][C:4]([C:7]2[N:8](S(C3C=CC=CC=3)(=O)=O)[C:9]3[C:14]([CH:15]=2)=[CH:13][C:12]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:11][CH:10]=3)=[CH:3][CH2:2]1.[OH-].[K+].C(=O)([O-])O.[Na+]>CO>[O:1]1[CH2:6][CH2:5][C:4]([C:7]2[NH:8][C:9]3[C:14]([CH:15]=2)=[CH:13][C:12]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:11][CH:10]=3)=[CH:3][CH2:2]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 516892Sodium BicarbonateHCID 22504420HCID 22504420, compound

Product 1

HCID 225043862-(5,6-dihydro-2H-4-pyranyl)-5-methanesulfonylindoleYield 86.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of the compound obtained in Example 14 (3) (28.8 mg) in methanol (3 ml), a 1N aqueous potassium hydroxide solution (0.69 ml) was added and the mixture was stirred at 100° C. for 1 hour. The reaction solution was then poured into a saturated aqueous sodium hydrogencarbonate solution, extracted with dichloromethane, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to obtain 16.5 mg of the desired product as a white powder.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-754321d5a5184cf3a59fb53c3b27bb7e
Source dataset
uspto-grants-2009_11
Patent number
US07612070B2

Reaction notes

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