m-Chloroperbenzoic acid → HCID 67300738, compound

HRID 1015444Notes

Reaction equation

HRID 1015444 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:13][CH:14]=3)[C:9]([S:21][CH3:22])=[C:8]2[CH3:23])=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:34])C=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:13][CH:14]=3)[C:9]([S:21]([CH3:22])=[O:34])=[C:8]2[CH3:23])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 67300467HCID 67300467, compound

Product 1

HCID 67300738HCID 67300738, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A 300 mg portion of ethyl 1-(4-fluorobenzyl)-2-methyl-3-(methylthio)-1H-indole-5-carboxylate was dissolved in 3 ml of chloroform, and 203 mg of 3-chloroperbenzoic acid was added under ice-cooling, followed by stirring at the same temperature for 1 hour. A saturated sodium bicarbonate aqueous solution was added to the reaction liquid, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. After evaporation of the solvent under a reduced pressure, the residue was purified by silica gel column chromatography (chloroform:methanol:hexane=1:0:1 to 1:0:0 to 100:1:0 to 50:1:0 to 30:1:0) to obtain 279 mg of ethyl 1-(4-fluorobenzyl)-2-methyl-3-(methylsulfinyl)-1H-indole-5-carboxylate as a colorless solid.

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter evaporation of the solvent under a reduced pressure
  6. customthe residue was purified by silica gel column chromatography (chloroform:methanol:hexane=1:0:1 to 1:0:0 to 100:1:0 to 50:1:0 to 30:1:0)

Sources & evidence

ORD record
ord-9ede6a0996824d1ba5e4d97172b6bd60
Source dataset
uspto-grants-2011_07
Patent number
US07985764B2

Reaction notes

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