Water → n-{2-[5-Hydroxy-1-(phenylsulphonyl)-1h-indol-3-yl]ethyl}acetamide

HRID 382325Notes

Reaction equation

HRID 382325 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:7]=[C:6]2[CH2:21][CH2:22][NH:23][C:24](=[O:26])[CH3:25].B(Br)(Br)Br.O>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:7]=[C:6]2[CH2:21][CH2:22][NH:23][C:24](=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 11090036n-{2-[5-Methoxy-1-(phenylsulphonyl)-1h-indol-3-yl]ethyl}acetamide

Product 1

HCID 18007950n-{2-[5-Hydroxy-1-(phenylsulphonyl)-1h-indol-3-yl]ethyl}acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5 g of the compound obtained in Step A are dissolved in 100 ml of dichloromethane. The reaction mixture is then cooled in an ice-bath, and 3.81 ml of boron tribromide are added dropwise. After stirring at room temperature for two hours, the reaction mixture is poured into 500 ml of water and ice. The precipitate that forms is filtered off, washed with water and oven-dried at 50° C.

Workup

  1. temperatureThe reaction mixture is then cooled in an ice-bath
  2. filtrationThe precipitate that forms is filtered off
  3. washwashed with water
  4. customoven-dried at 50° C.

Sources & evidence

ORD record
ord-0c9cbb4ffa174b4a97f8bfbb261f9ee8
Source dataset
uspto-grants-2001_10
Patent number
US06310074B1

Reaction notes

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