(1-(4-Fluorobenzyl)-5-methanesulfonylindol-2-yl)(thiazol-2-yl)-methanol → 1-(4-Fluorobenzyl)-5-methanesulfonyl-2-(2-thiazolylcarbonyl)indole

HRID 1838373Notes

Reaction equation

HRID 1838373 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:13][CH:14]=3)[CH:9]=[C:8]2[CH:20]([C:22]2[S:23][CH:24]=[CH:25][N:26]=2)[OH:21])=[CH:4][CH:3]=1>ClCCl.[O-2].[O-2].[Mn+4]>[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]([S:16]([CH3:19])(=[O:17])=[O:18])=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:20]([C:22]2[S:23][CH:24]=[CH:25][N:26]=2)=[O:21])=[CH:27][CH:28]=1

Participants

4

Reactant 1

HCID 22504451(1-(4-Fluorobenzyl)-5-methanesulfonylindol-2-yl)(thiazol-2-yl)-methanol

Product 1

HCID 225044221-(4-Fluorobenzyl)-5-methanesulfonyl-2-(2-thiazolylcarbonyl)indoleYield 45.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound obtained in Example 27 (5) (110 mg) in dichloromethane (20 ml), manganese dioxide (900 mg) was added at 15 to 30° C. and the mixture was stirred for 30 minutes. The reaction solution was then filtered through Celite and concentrated under reduced pressure. The resulting residue was subjected to silica gel preparative thin-layer chromatography (hexane:ethyl acetate=1:1) to obtain 50 mg of the desired products as a yellow powder.

Workup

  1. filtrationThe reaction solution was then filtered through Celite
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4cd8510273a3432fa69cc606fcb563ed
Source dataset
uspto-grants-2004_01
Patent number
US06673797B1

Reaction notes

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