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Potassium Phosphate, Tribasic → 1-Phenyl-2-(5-benzo[c]phenanthren-4-ylphenyl)benzimidazole

HRID 2371241
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HRID 2371241 반응식
C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[C:23]1([N:29]2[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=3[N:31]=[C:30]2[C:38]2[CH:43]=[CH:42][C:41](Br)=[CH:40][CH:39]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH:45]1[C:62]2[C:61]3[C:60]4[CH:59]=[CH:58][CH:57]=[CH:56][C:55]=4[CH:54]=[CH:53][C:52]=3[CH:51]=[C:50](B(O)O)[C:49]=2[CH:48]=[CH:47][CH:46]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.O1CCOCC1>[C:23]1([N:29]2[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=3[N:31]=[C:30]2[C:38]2[CH:43]=[C:42]([C:48]3[C:49]4[CH:50]=[CH:51][C:52]5[CH:53]=[CH:54][C:55]6[CH:56]=[CH:57][CH:58]=[CH:59][C:60]=6[C:61]=5[C:62]=4[CH:45]=[CH:46][CH:47]=3)[CH:41]=[CH:40][CH:39]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1
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참가 물질

9

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 80271Tri-o-tolylphosphineHCID 230940702-(4-Bromophenyl)-1-phenyl-1H-benzo(d)imidazoleHCID 59622711Benzo[c]phenanthren-5-ylboronic acid

생성물 1

HCID 866595461-Phenyl-2-(5-benzo[c]phenanthren-4-ylphenyl)benzimidazole

시약·촉매·용매 4

HCID 167845
palladium(II) acetate
촉매
HCID 962Water용매
HCID 1140Toluene용매
HCID 312751,4-Dioxane용매

실험 절차

913 mg (3 mmol) of tri-o-tolylphosphine and then 112 mg (0.5 mmol) of palladium(II) acetate are added to a vigorously stirred suspension of 17.5 g (50 mmol) of 1-phenyl-2-(4-bromophenyl)benzimidazole, 14.9 g (55 mmol) of benzo[c]phenanthrene-5-boronic acid and 25.5 g (120 mmol) of tripotassium phosphate in a mixture of 300 ml of toluene, 100 ml of dioxane and 400 ml of water, and the mixture is subsequently heated under reflux for 16 h. After the mixture has been cooled, the precipitated solid is filtered off with suction, washed three times with 50 ml of toluene, three times with 50 ml of ethanol:water (1:1, v:v) and three times with 100 ml of ethanol and recrystallised three times from DMF (about 7 ml/g). Yield: 16.8 g (34 mmol), 67.8%, purity 99.9% (HPLC).

후처리

  1. temperaturethe mixture is subsequently heated
  2. temperatureunder reflux for 16 h
  3. temperatureAfter the mixture has been cooled
  4. filtrationthe precipitated solid is filtered off with suction
  5. washwashed three times with 50 ml of toluene, three times with 50 ml of ethanol:water (1:1, v:v) and three times with 100 ml of ethanol
  6. customrecrystallised three times from DMF (about 7 ml/g)

출처 및 근거

ORD 기록
ord-005daff99dc74fc7bd2c56d5a2f89346
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08710284B2

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