Potassium Carbonate → HCID 59609504、化合物

HRID 468978ノート

反応式

HRID 468978 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:7]=[C:8](Br)[CH:9]=1)[CH:5]=O.[C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)(=O)[CH3:12].[I-].BrC1N=C(C(=O)C[N+:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)C=CC=1.BrC1N=[C:42]([C:44]2[CH:49]=[C:48]([C:50]3[CH:55]=[C:54](Br)[CH:53]=[C:52](Br)[CH:51]=3)[CH:47]=[C:46]([C:58]3[CH:63]=[CH:62][CH:61]=[CH:60]N=3)N=2)C=CC=1.[CH:64]1C2C3C=CC=CC=3NC=2C=CN=1.BrC1C=C(C2C=C(C3C=CC=CN=3)N=C(C3C=[CH:101][CH:100]=[C:99]([N:103]4C5C=CC=CC=5[C:105]5[CH:112]=[N:113][CH:114]=C[C:104]4=5)[N:98]=3)C=2)C=C(Br)C=1.C1(B(O)O)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>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.C1(C)C=CC=CC=1>[CH:114]1[C:5]2[C:4]3[CH:7]=[CH:8][CH:9]=[CH:2][C:3]=3[N:103]([C:99]3[N:98]=[C:11]([C:14]4[CH:19]=[C:18]([C:44]5[CH:42]=[C:46]([C:58]6[CH:63]=[CH:62][CH:61]=[CH:60][CH:64]=6)[CH:47]=[C:48]([C:50]6[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=6)[CH:49]=5)[CH:17]=[C:16]([C:35]5[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=5)[N:15]=4)[CH:12]=[CH:101][CH:100]=3)[C:104]=2[CH:105]=[CH:112][N:113]=1

参加物

12

反応物 8

HCID 11430Potassium CarbonateHCID 142862-AcetylpyridineHCID 66827Phenylboronic AcidHCID 130802Gamma-CarbolineHCID 6220773,5-DibromobenzaldehydeHCID 12786936HCID 12786936、化合物HCID 68625142HCID 68625142、化合物2 回HCID 87519798HCID 87519798、化合物

生成物 1

HCID 59609504HCID 59609504、化合物収率 41%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒

実験手順

As in Example 4,3-(3,5-dibromophenyl)-1-(pyridin-2-yl)-propenone was synthesized from 3,5-dibromobenzaldehyde and 2-acetylpyridine, and further subjected to a reaction with [2-(6-bromopyridin-2-yl)oxoethyl]pyridinium iodide to synthesize 6-bromo-4′-(3,5-dibromophenyl)-[2,2′;6′,2″]terpyridine. This compound was further subjected to a reaction with 5H-pyrido[4,3-b]indole to synthesize 4′-(3,5-dibromophenyl)-6-(5H-pyrido[4,3-b]indol-5-yl)-[2,2′;6′,2″]terpyridine. To 5.1 g of the resulting 4′-(3,5-dibromophenyl)-6-(5H-pyrido[4,3-b]indol-5-yl)-[2,2′;6′,2″]terpyridine were added 2.1 g of phenylboronic acid, 0.5 g of tetrakis(triphenylphosphine)palladium, 20 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 12 hours. After cooling to room temperature, the precipitate was collected by filtration. To the precipitate, 80 mL of chloroform was added and insoluble matter was removed by filtration. 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: toluene) and then recrystallized using o-dichlorobenzene. Thus, 2.1 g (yield, 41%) of 6-(5H-pyrido[4,3-b]indol-5-yl)-4′-[1,1′;3′,1″]terphenyl-5′-yl-[2,2′;6′,2″]terpyridine (Compound 136) was obtained as a white powder.

後処理

  1. temperatureby heating
  2. temperaturewith reflux
  3. filtrationthe precipitate was collected by filtration
  4. additionTo the precipitate, 80 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 crude product
  8. customThe crude product was purified by column chromatography (carrier: NH silica gel, eluent: toluene)
  9. customrecrystallized

出典と根拠

ORDレコード
ord-c6f85dd3e30f46f88c21ac365154872a
出典データセット
uspto-grants-2014_01
特許番号
US08624228B2

反応ノート

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