Nitrogen → 2-[4-(10-Phenanthren-3-ylanthracen-9-yl)phenyl]-1-phenyl-1h-benzimidazole

HRID 879925

反応式

HRID 879925 の反応式
BrC1[C:3]2[C:8]([C:9]([C:16]3[CH:17]=CC4C=CC5C(C=4[CH:29]=3)=CC=CC=5)=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[C:30]1([N:36]2[C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=3[N:38]=[C:37]2C2C=CC(B(O)O)=CC=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C([O-])([O-])=O.[Na+].[Na+].N#N.[C:62]1([CH3:68])[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1>CCO.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.O.CO>[CH:64]1[C:65]2[CH:10]=[CH:9][C:8]3[C:7](=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:66]=2[CH:67]=[C:62]([C:68]2[C:17]3[C:16](=[CH:29][CH:11]=[CH:12][CH:13]=3)[C:9]([C:10]3[CH:11]=[CH:12][C:13]([C:37]4[N:36]([C:30]5[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=5)[C:40]5[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=5[N:38]=4)=[CH:14][CH:15]=3)=[C:8]3[C:3]=2[CH:4]=[CH:5][CH:6]=[CH:7]3)[CH:63]=1

参加物

9

反応物 5

HCID 947NitrogenHCID 1140TolueneHCID 10340Sodium CarbonateHCID 532497794-(1-Phenyl-1H-benzimidazol-2-yl)phenylboronic AcidHCID 596295449-Bromo-10-phenanthren-3-ylanthracene

生成物 1

HCID 596295792-[4-(10-Phenanthren-3-ylanthracen-9-yl)phenyl]-1-phenyl-1h-benzimidazole収率 68%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 22242641Methanol--water (1/1)溶媒

実験手順

32 g (70 mmol) of 9-bromo-10-phenanthren-3-ylanthracene, 26.3 g (84 mmol) of 4-(1-phenyl-1H-benzimidazol-2-yl)phenylboronic acid and 125 ml of 2 M Na2CO3 solution are suspended in 500 ml of toluene and 500 ml of EtOH, the mixture is saturated with N2, 1.7 g (1.8 mmol) of tetrakis(triphenylphosphine)palladium(0) are added, and the mixture is heated at the boil for 2 h. The mixture is poured into 1.5 l of a mixture of water/MeOH/6 M HCl 1:1:1, and the yellow precipitate is filtered off with suction, washed with water, EtOH and toluene and dried. Subsequent Soxhlet extraction with chloroform, removal of the solvent, recrystallisation three times from toluene and sublimation twice in vacuo (p=1×10−5 mbar, T=385° C.) give 30 g (68%) of a pale-yellow powder having a purity of >99.9% (HPLC).

後処理

  1. additionare added
  2. temperaturethe mixture is heated at the boil for 2 h
  3. filtrationthe yellow precipitate is filtered off with suction
  4. washwashed with water, EtOH and toluene
  5. customdried
  6. extractionSubsequent Soxhlet extraction
  7. customwith chloroform, removal of the solvent, recrystallisation three times from toluene and sublimation twice in vacuo (p=1×10−5 mbar, T=385° C.)

出典と根拠

ORDレコード
ord-ab83d728c9b84a7caab39f2bdb2bb0db
出典データセット
uspto-grants-2015_03
特許番号
US08993123B2

関連ノート

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