m-Chloroperbenzoic acid → HCID 67300489, compound

HRID 1015445Notes

Reaction equation

HRID 1015445 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](SC)=[C:8]2[CH3:23])=[CH:4][CH:3]=1.Cl[C:27]1C=CC=C(C(OO)=O)C=1.[S:37]([O-:40])(O)=[O:38].[Na+]>C(Cl)(Cl)Cl>[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:37]([CH3:27])(=[O:40])=[O:38])=[C:8]2[CH3:23])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 23665763Sodium BisulfiteHCID 67300467HCID 67300467, compound

Product 1

HCID 67300489HCID 67300489, 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 483 mg of 3-chloroperbenzoic acid under ice-cooling was added, followed by stirring at the same temperature for 30 minutes and then at room temperature for 1 hour. A 10% sodium hydrogen sulfite aqueous solution was added to the reaction liquid, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium bicarbonate aqueous solution and 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 (ethyl acetate:hexane:chloroform=0.2:1:1 to 0.3:1:1 to 0.4:1:1) to obtain 285 mg of ethyl 1-(4-fluorobenzyl)-2-methyl-3-(methylsulfonyl)-1H-indole-5-carboxylate as a pale green solid.

Workup

  1. additionwas added
  2. waitat room temperature for 1 hour
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with a saturated sodium bicarbonate aqueous solution and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customAfter evaporation of the solvent under a reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane:chloroform=0.2:1:1 to 0.3:1:1 to 0.4:1:1)

Sources & evidence

ORD record
ord-6deb0f24e8264d1cb21c3d1338e657ce
Source dataset
uspto-grants-2011_07
Patent number
US07985764B2

Reaction notes

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