Potassium Carbonate → HCID 59609465, compound

HRID 468977Notes

Reaction equation

HRID 468977 reaction equation
C(C1C=CC=CN=1)(=O)C.[I-].BrC1N=C(C(=O)C[N+]2C=CC=CC=2)C=CC=1.[C:27]1([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:33]1[CH:38]=[C:37]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=2)[N:36]=[C:35]([C:45]2[CH:50]=[CH:49][CH:48]=[C:47](Br)[N:46]=2)[CH:34]=1.[CH:58]1[C:70]2[C:69]3[CH:68]=[CH:67][CH:66]=[CH:65][C:64]=3[NH:63][C:62]=2[CH:61]=[CH:60][N:59]=1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl.[Cu].ClC1C=CC=CC=1Cl.CS(C)=O>[C:27]1([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:33]1[CH:38]=[C:37]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=2)[N:36]=[C:35]([C:45]2[CH:50]=[CH:49][CH:48]=[C:47]([N:63]3[C:64]4[CH:65]=[CH:66][CH:67]=[CH:68][C:69]=4[C:70]4[CH:58]=[N:59][CH:60]=[CH:61][C:62]3=4)[N:46]=2)[CH:34]=1

Participants

10

Reactant 5

HCID 11430Potassium CarbonateHCID 142862-AcetylpyridineHCID 130802gamma-CarbolineHCID 12786936HCID 12786936, compoundHCID 86648285HCID 86648285, compound2×

Product 1

HCID 59609465HCID 59609465, compoundYield 46%

Reagents, catalysts & solvents 4

HCID 23978CopperCatalystHCID 679Dimethyl SulfoxideSolventHCID 6212ChloroformSolvent2×HCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
140 °C

Procedure

As in Example 1,3-(biphenyl-2-yl)-1-(pyridin-2-yl)propenone was synthesized from 2-biphenylcarboxyaldehyde and 2-acetylpyridine, and further subjected to a reaction with [2-(6-bromopyridin-2-yl)oxoethyl]pyridinium iodide to synthesize 4′-(biphenyl-2-yl)-6-bromo[2,2′;6′,2″]terpyridine. To 4.6 g of the resulting 4′-(biphenyl-2-yl)-6-bromo[2,2′;6′,2″]terpyridine were added 1.7 g of 5H-pyrido[4,3-b]indole, 0.3 g of a copper powder, 4.2 g of potassium carbonate, 0.3 mL of dimethyl sulfoxide, and 20 mL of o-dichlorobenzene, followed by heating and stirring at 140° C. for 5 hours. After cooling to room temperature, 60 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. The concentrate was dissolved in chloroform, and subjected to adsorptive purification with NH silica gel and to concentration under a reduced pressure to obtain a crude product. The crude product was washed with methanol and further washed with ethyl acetate to obtain 2.6 g (yield, 46%) of 4′-(biphenyl-2-yl)-6-(5H-pyrido[4,3-b]indol-5-yl)-[2,2′;6′,2″]terpyridine (Compound 135) 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 concentrate
  7. customsubjected to adsorptive purification with NH silica gel and to concentration under a reduced pressure
  8. customto obtain a crude product
  9. washThe crude product was washed with methanol
  10. washfurther washed with ethyl acetate

Sources & evidence

ORD record
ord-51057c2a37e44aceabcdbf342bfd9eca
Source dataset
uspto-grants-2014_01
Patent number
US08624228B2

Reaction notes

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