Dodecane → HCID 58202941, compound

HRID 468971Notes

Reaction equation

HRID 468971 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[C:12]([C:14]3[CH:23]=[CH:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH:15]=3)[CH:11]=[C:10]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)[N:9]=2)[CH:5]=[CH:4][CH:3]=1.[CH:30]1[C:42]2[C:41]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[NH:35][C:34]=2[CH:33]=[CH:32][N:31]=1.C(=O)([O-])[O-].[K+].[K+].CCCCCCCCCCCC>[Cu].C(Cl)(Cl)Cl.CS(C)=O>[CH:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:22]=[CH:23][C:14]=1[C:12]1[CH:11]=[C:10]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)[N:9]=[C:8]([C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([N:35]3[C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][C:41]=4[C:42]4[CH:30]=[N:31][CH:32]=[CH:33][C:34]3=4)[N:7]=2)[CH:13]=1

Participants

8

Reactant 4

HCID 8182DodecaneHCID 11430Potassium CarbonateHCID 130802gamma-CarbolineHCID 86648282HCID 86648282, compound

Product 1

HCID 58202941HCID 58202941, compoundYield 44%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 679Dimethyl SulfoxideSolventHCID 6212ChloroformSolvent

Conditions

Temperature
150 °C

Procedure

To 4.2 g of the resulting 6-bromo-4′-(naphthalen-2-yl)-[2,2′;6′,2″]terpyridine were added 1.6 g of 5H-pyrido[4,3-b]indole, 0.3 g of a copper powder, 4.0 g of potassium carbonate, 0.3 mL of dimethyl sulfoxide, and 10 mL of n-dodecane, followed by heating and stirring at 150° C. for 8 hours. After cooling to room temperature, 80 mL of chloroform was added thereto to remove an insoluble matter by filtration, and the filtrate was concentrated under a reduced pressure to obtain a crude product. The crude product was purified by column chromatography (carrier: NH silica gel, eluent: hexane/chloroform) to obtain 2.2 g (yield, 43%) of 4′-(naphthalen-2-yl)-6-(5H-pyrido[4,3-b]indol-5-yl)-[2,2′;6′,2″]terpyridine (Compound 27) as a white powder.

Workup

  1. temperatureby heating
  2. temperatureAfter cooling to room temperature
  3. customto remove an insoluble matter
  4. filtrationby filtration
  5. concentrationthe filtrate was concentrated under a reduced pressure
  6. customto obtain a crude product
  7. customThe crude product was purified by column chromatography (carrier: NH silica gel, eluent: hexane/chloroform)

Sources & evidence

ORD record
ord-887bfed8edaa4affa12d1067d1097bc9
Source dataset
uspto-grants-2014_01
Patent number
US08624228B2

Reaction notes

Loading…