Potassium Carbonate → HCID 118006062, compound

HRID 929281Notes

Reaction equation

HRID 929281 reaction equation
[C:1]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=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[C:20]([CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:19][CH:18]=[CH:17][C:16]=3[C:12]=2[CH:11]=[CH:10][CH:9]=1.I[C:34]1[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=1.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>[Cu]>[C:1]1([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]([C:34]1[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=1)[C:8]1[C:13]2[O:14][C:15]3[C:20]([CH:21]4[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]4)=[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 118006142HCID 118006142, compound

Product 1

HCID 118006062HCID 118006062, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

N-([1,1′-biphenyl]-2-yl)-6-cyclohexyldibenzo[b,d]furan-4-amine (8.3 g. 20.0 mmol), 4-iodoanisole (18.7 g, 80.0 mmol), potassium carbonate (5.5 g, 40.0 mmol), copper powder (1.3 g, 20.0 mmol), and 18-crown-6 ether (5.3 g, 20.0 mmol) were mixed. The resultant mixture was bubbled with nitrogen for 30 min. The mixture was refluxed for 20 h. After cooling, the solvent was removed in vacuo and the residue was purified by flash chromatography using 15% DCM/hexane (containing 1% triethylamine) to yield N-([1,1′-biphenyl]-2-yl)-6-cyclohexyl-N-(4-methoxyphenyl)dibenzo[b,d]furan-4-amine (9.0 g, 86% yield) as a white solid.

Workup

  1. customThe resultant mixture was bubbled with nitrogen for 30 min
  2. temperatureThe mixture was refluxed for 20 h
  3. temperatureAfter cooling
  4. customthe solvent was removed in vacuo
  5. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-172a1fa1421f409b8e4ef59834539d6b
Source dataset
uspto-grants-2016_03
Patent number
US09293712B2

Reaction notes

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