Potassium Carbonate → N-([1,1'-biphenyl]-2-yl)-N-(4-methoxyphenyl)dibenzo[b,d]furan-4-amine

HRID 929275Notes

Reaction equation

HRID 929275 reaction equation
[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[C:13]2[O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:12]=2[CH:11]=[CH:10][CH:9]=1.I[C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>[Cu]>[C:1]1([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]([C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=1)[C:8]1[C:13]2[O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:12]=2[CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 696764-IodoanisoleHCID 68904161N-[1,1'-Biphenyl]-2-YL-4-dibenzofuranamine

Product 1

HCID 118005961N-([1,1'-biphenyl]-2-yl)-N-(4-methoxyphenyl)dibenzo[b,d]furan-4-amineYield 83%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

N-([1,1′-biphenyl]-2-yl)dibenzo[b,d]furan-4-amine (9.0 g, 27.0 mmol), 4-iodoanisole (23.4 g, 100.0 mmol), potassium carbonate (13.8 g, 100.0 mmol), copper powder (1.7 g, 27.0 mmol), and 18-crown-6 ether (7.1 g, 27.0 mmol) were mixed. The resultant mixture was bubbled with nitrogen for 30 min. The mixture was then refluxed for 48 h. After cooling, the solvent was removed in vacuo and the residue was purified by flash chromatography using 25% DCM/hexane (containing 0.5% triethylamine) to yield N-([1,1′-biphenyl]-2-yl)-N-(4-methoxyphenyl)dibenzo[b,d]furan-4-amine (9.9 g, 83% yield) as a colorless oil.

Workup

  1. customThe resultant mixture was bubbled with nitrogen for 30 min
  2. temperatureThe mixture was then refluxed for 48 h
  3. temperatureAfter cooling
  4. customthe solvent was removed in vacuo
  5. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-136f1bce015e4e829d491a388adae258
Source dataset
uspto-grants-2016_03
Patent number
US09293712B2

Reaction notes

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