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

HRID 2292811Notes

Reaction equation

HRID 2292811 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-9f316d99e96145ccaa544ddb7e32fa18
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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