Sodium Bicarbonate → 2-bromo-5-hydroxy-1-(phenylmethyl)-1H-indole-3-acetamide

HRID 1069654Notes

Reaction equation

HRID 1069654 reaction equation
[Br:1][C:2]1[N:3]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:4]2[C:9]([C:10]=1[CH2:11][C:12]([NH2:14])=[O:13])=[CH:8][C:7]([O:15]C)=[CH:6][CH:5]=2.B(Br)(Br)Br.C(Cl)Cl.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Br:1][C:2]1[N:3]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:4]2[C:9]([C:10]=1[CH2:11][C:12]([NH2:14])=[O:13])=[CH:8][C:7]([OH:15])=[CH:6][CH:5]=2

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 108093422-bromo-5-methoxy-1-(phenylmethyl)-1H-indole-3-acetamideHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 105946062-bromo-5-hydroxy-1-(phenylmethyl)-1H-indole-3-acetamideYield 34.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4 g (11 mmol) of 2-bromo-5-methoxy-1-(phenylmethyl)-1H-indole-3-acetamide and 35 mL of BBr3/methylene chloride in 200 mL of methylene chloride was stirred for 1 hour, poured into ice-water, made basic with sodium bicarbonate and extracted with methylene chloride. This solution was washed with brine, dried (Na2SO4) and concentrated. The residue was chromatographed on silica gel and eluted with ethyl acetate to give 1.35 g (33% yield) of 2-bromo-5-hydroxy-1-(phenylmethyl)-1H-indole-3-acetamide.

Workup

  1. extractionextracted with methylene chloride
  2. washThis solution was washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel
  6. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-4926e223ef474db4ad862ae34d38d2c8
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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