Boron tribromide → 2-ethyl-5-hydroxy-1-(phenylmethyl)-1H-indole-3-acetamide

HRID 1069610Notes

Reaction equation

HRID 1069610 reaction equation
[CH2:1]([C:3]1[N:4]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:5]2[C:10]([C:11]=1[CH2:12][C:13]([NH2:15])=[O:14])=[CH:9][C:8]([O:16]C)=[CH:7][CH:6]=2)[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([C:3]1[N:4]([CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:5]2[C:10]([C:11]=1[CH2:12][C:13]([NH2:15])=[O:14])=[CH:9][C:8]([OH:16])=[CH:7][CH:6]=2)[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 106158292-Ethyl-5-methoxy-1-(phenylmethyl)-1H-indole-3-acetamide

Product 1

HCID 105428362-ethyl-5-hydroxy-1-(phenylmethyl)-1H-indole-3-acetamideYield 75.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Ethyl-5-methoxy-1-(phenylmethyl)-1H-indole-3-acetamide (5.05 g, 15.7 mmol) and 47 mL of 1M BBr3 in 100 mL of methylene chloride was reacted as described in Example 56, Part C to give a product that was chromatographed on silica gel eluting with EtOAc to give 3.64 g (75% yield) of 2-ethyl-5-hydroxy-1-(phenylmethyl)-1H-indole-3-acetamide as a yellow foam.

Workup

  1. customto give a product that
  2. customwas chromatographed on silica gel eluting with EtOAc

Sources & evidence

ORD record
ord-4067022e1394400b91fe36065eae52bf
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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