Potassium Carbonate → HCID 86762385, compound

HRID 1021172Notes

Reaction equation

HRID 1021172 reaction equation
[C:1]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:6]=[CH:5][C:4]([NH:7][C:8]2[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:12][CH:11]=[CH:10][C:9]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:3][CH:2]=1.I[C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=1.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>[Cu].ClC1C=CC=CC=1Cl>[C:1]1([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:6]=[CH:5][C:4]([N:7]([C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=2)[C:8]2[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:12][CH:11]=[CH:10][C:9]=2[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 696764-IodoanisoleHCID 86762384HCID 86762384, compound

Product 1

HCID 86762385HCID 86762385, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 72391,2-DichlorobenzeneSolvent

Procedure

N-([1,1′-biphenyl]-4-yl)[1,1′:3′,1″-terphenyl]-2′-amine (15.9 g, 40.0 mmol), 4-iodoanisole (37.4 g, 160.0 mmol), potassium carbonate (22.1 g, 160.0 mmol), copper powder (5.1 g, 80.0 mmol), 18-crown-6 ether (21.1 g, 80.0 mmol) and 1,2-dichlorobenzene (200 mL) were bubbled with nitrogen for 30 min. The mixture was refluxed for 72 h. After cooling, the reaction mixture was filtered through a silica pad and washed with toluene (containing 0.5% triethylamine). The solvent was removed in vacuo and the residue was purified by flash chromatography using 40-50% toluene/hexane (containing 0.5% triethylamine) to afford N-([1,1′-biphenyl]-4-yl)-N-(4-methoxyphenyl)-[1,1′:3′,1″-terphenyl]-2′-amine (10.3 g, 51% yield) as a white solid.

Workup

  1. temperatureThe mixture was refluxed for 72 h
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtered through a silica pad
  4. washwashed with toluene (containing 0.5% triethylamine)
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-8c7719201e16465fab91c2a386935566
Source dataset
uspto-grants-2014_05
Patent number
US08716484B1

Reaction notes

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