Potassium Carbonate → HCID 68625661, compound

HRID 468974Notes

Reaction equation

HRID 468974 reaction equation
BrC1C=CC(C=O)=CC=1.C(C1C=CC=CN=1)(=O)C.[I-].BrC1N=C(C(=O)C[N+]2C=CC=CC=2)C=CC=1.Br[C:37]1[N:42]=[C:41]([C:43]2[CH:48]=[C:47]([C:49]3[CH:54]=[CH:53][C:52]([Br:55])=[CH:51][CH:50]=3)[CH:46]=[C:45]([C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][N:57]=3)[N:44]=2)[CH:40]=[CH:39][CH:38]=1.[CH:62]1[C:74]2[C:73]3[CH:72]=[CH:71][CH:70]=[CH:69][C:68]=3[NH:67][C:66]=2[CH:65]=[CH:64][N:63]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu].C1(C)C=CC=CC=1.C(Cl)(Cl)Cl.ClC1C=CC=CC=1Cl.CS(C)=O>[Br:55][C:52]1[CH:53]=[CH:54][C:49]([C:47]2[CH:46]=[C:45]([C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][N:57]=3)[N:44]=[C:43]([C:41]3[CH:40]=[CH:39][CH:38]=[C:37]([N:67]4[C:68]5[CH:69]=[CH:70][CH:71]=[CH:72][C:73]=5[C:74]5[CH:62]=[N:63][CH:64]=[CH:65][C:66]4=5)[N:42]=3)[CH:48]=2)=[CH:50][CH:51]=1

Participants

12

Reactant 6

HCID 11430Potassium CarbonateHCID 142862-AcetylpyridineHCID 707414-BromobenzaldehydeHCID 130802gamma-CarbolineHCID 12786936HCID 12786936, compoundHCID 86648284HCID 86648284, compound2×

Product 1

HCID 68625661HCID 68625661, compoundYield 62%

Reagents, catalysts & solvents 5

HCID 23978CopperCatalystHCID 679Dimethyl SulfoxideSolventHCID 1140TolueneSolventHCID 6212ChloroformSolventHCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
120 °C

Procedure

As in Example 1,3-(4-bromophenyl)-1-(pyridin-2-yl)propenone was synthesized from 4-bromobenzaldehyde and 2-acetylpyridine, and further subjected to a reaction with [2-(6-bromopyridin-2-yl)oxoethyl]pyridinium iodide to synthesize 6-bromo-4′-(4-bromophenyl)-[2,2′;6′,2″]terpyridine. To 15.3 g of the resulting 6-bromo-4′-(4-bromophenyl)-[2,2′;6′,2″]terpyridine were added 5.6 g of 5H-pyrido[4,3-b]indole, 1.0 g of a copper powder, 6.8 g of potassium carbonate, 1.0 mL of dimethyl sulfoxide, and 80 mL of o-dichlorobenzene, followed by heating and stirring at 120° C. for 7 hours. After cooling to room temperature, 200 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 concentrate. To the concentrate, 2 L of toluene was added and insoluble matter was removed by filtration. NH silica gel was added to the filtrate to perform adsorptive purification. Thereafter, the filtrate was concentrated under a reduced pressure to obtain a crude product. The crude product obtained was washed with methanol to obtain 11.3 g (yield, 62%) of 4′-(4-bromophenyl)-6-(5H-pyrido[4,3-b]indol-5-yl)-[2,2′;6′,2″]terpyridine as a brown 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 concentrate
  7. custominsoluble matter was removed by filtration
  8. additionNH silica gel was added to the filtrate
  9. custompurification
  10. concentrationThereafter, the filtrate was concentrated under a reduced pressure
  11. customto obtain a crude product
  12. customThe crude product obtained
  13. washwas washed with methanol

Sources & evidence

ORD record
ord-24c62f6cea084e0481eb76f66c1bd445
Source dataset
uspto-grants-2014_01
Patent number
US08624228B2

Reaction notes

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