Iodobenzene → HCID 9994551, compound

HRID 222695Notes

Reaction equation

HRID 222695 reaction equation
[H-].[Na+].[CH:3]1([N:7]2[CH2:13][CH2:12][C:11]3[CH:14]=[C:15]([OH:18])[CH:16]=[CH:17][C:10]=3[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4]1.I[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>N1C=CC=CC=1.[Cu]Br>[CH:3]1([N:7]2[CH2:13][CH2:12][C:11]3[CH:14]=[C:15]([O:18][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:16]=[CH:17][C:10]=3[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 11575IodobenzeneHCID 24758Sodium hydrideHCID 100820813-Cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[D]azepin-7-OL

Product 1

HCID 9994551HCID 9994551, compound

Reagents, catalysts & solvents 2

HCID 24593copper(I) bromideCatalystHCID 1049PyridineSolvent

Procedure

Sodium hydride (60% disp. in mineral oil, 96 mg, 2.4 mmol) was added to a stirred solution of 3-cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ol (E3) (435 mg, 2.0 mmol) and copper (I) bromide (402 mg, 2.8 mmol) in pyridine (10 ml) at 0° C. After stirring for 0.5 hour at room temperature, iodobenzene (0.45 ml, 4.0 mmol) was added and the reaction mixture was heated to reflux for 24 hours. The reaction was allowed to cool, filtered and the filtrate then concentrated in vacuo. The crude residue was dissolved with ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo and the resulting residue purified by column chromatography eluting with a mixture of 0.880 ammonia:ethanol:dichloromethane (0.25:2.25:97.5 to 1:9:90) to afford the title compound (E128); MS (ES+) m/e 294 [M+H]+.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 24 hours
  3. temperatureto cool
  4. filtrationfiltered
  5. concentrationthe filtrate then concentrated in vacuo
  6. dissolutionThe crude residue was dissolved with ethyl acetate
  7. washwashed with water and brine
  8. dry with materialThe organic layer was dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customthe resulting residue purified by column chromatography
  12. washeluting with a mixture of 0.880 ammonia:ethanol:dichloromethane (0.25:2.25:97.5 to 1:9:90)

Sources & evidence

ORD record
ord-317901ecdae24a07873eeaa3456eb21b
Source dataset
uspto-grants-2012_06
Patent number
US08207331B2

Reaction notes

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