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

HRID 879925

반응식

HRID 879925 반응식
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

참가 물질

9

반응물 5

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

생성물 1

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

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 22242641Methanol--water (1/1)용매

실험 절차

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).

후처리

  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.)

출처 및 근거

ORD 기록
ord-ab83d728c9b84a7caab39f2bdb2bb0db
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993123B2

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