Iodobenzene → HCID 21191835, compound

HRID 2292814Notes

Reaction equation

HRID 2292814 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]([CH3:18])=[C:5]2[CH2:19][C:20]([NH2:22])=[O:21].[H-].[Na+].I[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>N1C=CC=CC=1.C(OCC)(=O)C.Cl>[CH3:18][C:6]1[N:7]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]2[C:4]([C:5]=1[CH2:19][C:20]([NH2:22])=[O:21])=[CH:3][C:2]([O:1][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[CH:10][CH:9]=2

Participants

7

Reactant 3

HCID 11575IodobenzeneHCID 24758Sodium hydrideHCID 10589888HCID 10589888, compound

Product 1

HCID 21191835HCID 21191835, compoundYield 3%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Hydroxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetamide (1.2 g, 4.1 mmol) was dissolved in 40 mL of pyridine, 90 mg (2.2 mmol) of 60% NaH/mineral oil added, stirred 0.17 hours, 315 mg of CuO added, stirred 0.17 hours and 0.5 (4.1 mmol) mL of iodobenzene added. The mixture was heated to maintain reflux for 24 hours, cooled, and diluted with ethyl acetate and 1N HCl. The mixture was filtered thru a celite pad and the organic material separated, washed with brine, dried (Na2SO4) and concentrated at reduced pressure. The residue was chromatographed on silica gel and eluted with 1% MeOH/methylene chloride→3% MeOH/methylene chloride to give 40 mg (3% yield) of 2-methyl-5-phenoxy-1-(phenylmethyl)-1H-indole-3-acetamide.

Workup

  1. stirringstirred 0.17 hours
  2. temperatureThe mixture was heated
  3. temperatureto maintain
  4. temperaturereflux for 24 hours
  5. temperaturecooled
  6. filtrationThe mixture was filtered
  7. customthe organic material separated
  8. washwashed with brine
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated at reduced pressure
  11. customThe residue was chromatographed on silica gel
  12. washeluted with 1% MeOH/methylene chloride→3% MeOH/methylene chloride

Sources & evidence

ORD record
ord-fddbe340be33444fa71f165ec48262bb
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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