Water → HCID 21191849, compound

HRID 1069601Notes

Reaction equation

HRID 1069601 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:7]([CH3:20])=[C:6]2[CH2:21][C:22]([NH2:24])=[O:23].B(Br)(Br)Br.C(Cl)Cl.O.C(OCC)(=O)C>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:7]([CH3:20])=[C:6]2[CH2:21][C:22]([NH2:24])=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21191893HCID 21191893, compoundHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 21191849HCID 21191849, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.03 g (3.1 mmol) of 5-methoxy-2-methyl-1-octyl-1H-indole-3-acetamide and 5 mL of 1M BBr3/methylene chloride in 50 mL of methylene chloride was stirred for 24 hours, poured into water and 150 mL of ethyl acetate added. The organic layer was separated, washed with NaHCO3 solution, dried (Na2SO4) and concentrated at reduced pressure. The residue was chromatographed on silica gel by eluting with 5% MeOH/methylene chloride to give 16 mg (32% yield) of 5-hydroxy-2-methyl-1-octyl-1H-indole-3-acetamide.

Workup

  1. additionadded
  2. customThe organic layer was separated
  3. washwashed with NaHCO3 solution
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated at reduced pressure
  6. customThe residue was chromatographed on silica gel
  7. washby eluting with 5% MeOH/methylene chloride

Sources & evidence

ORD record
ord-21a6976f49ae45d793a588a0e3c58703
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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