2-Naphthalenecarboxaldehyde → HCID 59609565, compound

HRID 468973Notes

Reaction equation

HRID 468973 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=O.C(C1C=CN=CC=1)(=O)C.[I-].BrC1N=C(C(=O)C[N+]2C=CC=CC=2)C=CC=1.Br[C:40]1[N:45]=[C:44]([C:46]2[CH:51]=C(C3C=CC4C(=CC=CC=4)C=3)[CH:49]=[C:48]([C:62]3[CH:67]=[CH:66][N:65]=[CH:64][CH:63]=3)[N:47]=2)[CH:43]=[CH:42][CH:41]=1.BrC1C(C2C=C(C3C=CC4C(=CC=CC=4)C=3)C=C(C3C=CN=CC=3)N=2)=NC=CC=1.[CH:97]1[C:109]2[C:108]3[CH:107]=[CH:106][CH:105]=[CH:104][C:103]=3[NH:102][C:101]=2[CH:100]=[CH:99][N:98]=1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl.[Cu].ClC1C=CC=CC=1Cl.CS(C)=O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[CH:49]=[C:48]([C:62]2[CH:63]=[CH:64][N:65]=[CH:66][CH:67]=2)[N:47]=[C:46]([C:44]2[CH:43]=[CH:42][CH:41]=[C:40]([N:102]3[C:103]4[CH:104]=[CH:105][CH:106]=[CH:107][C:108]=4[C:109]4[CH:97]=[N:98][CH:99]=[CH:100][C:101]3=4)[N:45]=2)[CH:51]=1

Participants

12

Reactant 7

HCID 62012-NaphthalenecarboxaldehydeHCID 11430Potassium CarbonateHCID 142824-AcetylpyridineHCID 130802gamma-CarbolineHCID 12786936HCID 12786936, compoundHCID 87521311HCID 87521311, compoundHCID 89915108HCID 89915108, compound

Product 1

HCID 59609565HCID 59609565, compoundYield 85%

Reagents, catalysts & solvents 4

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

Conditions

Temperature
140 °C

Procedure

As in Example 1,3-(naphthalen-2-yl)-1-(pyridin-4-yl)propenone was synthesized from 2-naphthaldehyde and 4-acetylpyridine, and further subjected to a reaction with [2-(6-bromopyridin-2-yl)oxoethyl]pyridinium iodide to synthesize 6-bromo-4′-(naphthalen-2-yl)-[2,2′;6′,4″]terpyridine. To 5.0 g of the resulting 6 bromo-4′-(naphthalen-2-yl)-[2,2′;6′,4″]terpyridine were added 1.9 g of 5H-pyrido[4,3-b]indole, 0.4 g of a copper powder, 4.7 g of potassium carbonate, 0.4 mL of dimethyl sulfoxide, and 22 mL of o-dichlorobenzene, followed by heating and stirring at 140° C. for 5.5 hours. After cooling to room temperature, 800 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 dissolved in chloroform and subjected to adsorptive purification with NH silica gel and then to recrystallization using o-dichlorobenzene. Thus, 5.1 g (yield, 85%) of 4′-(naphthalen-2-yl)-6-(5H-pyrido[4,3-b]indol-5-yl)-[2,2′;6′,4″]terpyridine (Compound 132) was obtained 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. customsubjected to adsorptive purification with NH silica gel
  8. customto recrystallization

Sources & evidence

ORD record
ord-c4e57361a25044579dae140fb7b50ce8
Source dataset
uspto-grants-2014_01
Patent number
US08624228B2

Reaction notes

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