Water → 2-cyclopropyl-5-hydroxy-1-(phenylmethyl)-1H-indole-3-acetamide

HRID 1069644Notes

Reaction equation

HRID 1069644 reaction equation
[CH:1]1([C:4]2[N:5]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:6]3[C:11]([C:12]=2[CH2:13][C:14]([NH2:16])=[O:15])=[CH:10][C:9]([O:17]C)=[CH:8][CH:7]=3)[CH2:3][CH2:2]1.B(Br)(Br)Br.C(Cl)Cl.O.C(OCC)(=O)C>C(Cl)Cl>[CH:1]1([C:4]2[N:5]([CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:6]3[C:11]([C:12]=2[CH2:13][C:14]([NH2:16])=[O:15])=[CH:10][C:9]([OH:17])=[CH:8][CH:7]=3)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 105928422-cyclopropyl-5-methoxy-1-(phenylmethyl)-1H-indole-3-acetamideHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 106635022-cyclopropyl-5-hydroxy-1-(phenylmethyl)-1H-indole-3-acetamideYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 400 mg (1.2 mmol) of 2-cyclopropyl-5-methoxy-1-(phenylmethyl)-1H-indole-3-acetamide and 2 mL of 1M BBr3/methylene chloride in 130 mL of methylene chloride was stirred for 1 hour with an ice-water bath and 3 hours at room temperature. The mixture was poured into water, 200 mL of ethyl acetate added, the organic layer separated, washed with brine and dried (Na2SO4). After concentrating at reduced pressure, the residue was crystallized from ethyl acetate to give 300 mg (79% yield) of 2-cyclopropyl-5-hydroxy-1-(phenylmethyl)-1H-indole-3-acetamide, mp, 174-175° C.

Workup

  1. additionadded
  2. customthe organic layer separated
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationAfter concentrating at reduced pressure
  6. customthe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-873fa58df45f427ab298a36f17bbb1d8
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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