Toluene → HCID 59609530, compound

HRID 468975Notes

Reaction equation

HRID 468975 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[N:11]=[C:10]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([N:26]4[C:34]5[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=5[C:28]5[CH:35]=[N:36][CH:37]=[CH:38][C:27]4=5)[N:21]=3)[CH:9]=2)=[CH:4][CH:3]=1.[C:39]1(B(O)O)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>C(Cl)(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C>[C:2]1([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[N:11]=[C:10]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([N:26]4[C:34]5[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=5[C:28]5[CH:35]=[N:36][CH:37]=[CH:38][C:27]4=5)[N:21]=3)[CH:9]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 68625661HCID 68625661, compound

Product 1

HCID 59609530HCID 59609530, compoundYield 58.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

To 5.1 g of the resulting 4′-(4-bromophenyl)-6-(5H-pyrido[4,3-b]indol-5-yl)-[2,2′;6′,2″]terpyridine were added 1.1 g of phenylboronic acid, 0.5 g of tetrakis(triphenylphosphine)palladium, 23 mL of a 2 M aqueous potassium carbonate solution, 72 mL of toluene, and 18 mL of ethanol, followed by heating with reflux while stirring for 5.5 hours. After cooling to room temperature, a precipitate was collected by filtration. To the precipitate, 200 mL of chloroform was added and insoluble matter was removed by filtration. The filtrate was concentrated under a reduced pressure to obtain a concentrate. The concentrate was dissolved in chloroform and subjected to adsorptive purification with NH silica gel. Thereafter, the filtrate was concentrated under a reduced pressure to obtain a crude product. The crude product was washed with methanol to obtain 2.9 g (yield, 57%) of 4′-(biphenyl-4-yl)-6-(5H-pyrido[4,3-b]indol-5-yl)-[2,2′;6′,2″]terpyridine (Compound 133) as a white powder.

Workup

  1. temperatureby heating
  2. temperaturewith reflux
  3. filtrationa precipitate was collected by filtration
  4. additionTo the precipitate, 200 mL of chloroform was added
  5. custominsoluble matter was removed by filtration
  6. concentrationThe filtrate was concentrated under a reduced pressure
  7. customto obtain a concentrate
  8. customsubjected to adsorptive purification with NH silica gel
  9. concentrationThereafter, the filtrate was concentrated under a reduced pressure
  10. customto obtain a crude product
  11. washThe crude product was washed with methanol

Sources & evidence

ORD record
ord-6f2cf40e7dcc434c9c939c102b149f85
Source dataset
uspto-grants-2014_01
Patent number
US08624228B2

Reaction notes

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