Potassium Phosphate, Tribasic → 9-Biphenyl-2-ylbenzo[4,5]imidazo[2,1-a]isoquinoline

HRID 519421노트

반응식

HRID 519421 반응식
C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.Br[C:24]1[CH:25]=[CH:26][C:27]2[N:40]=[C:31]3[C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][C:37]=4[CH:38]=[CH:39][N:30]3[C:28]=2[CH:29]=1.[C:41]1([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:42](B(O)O)=[CH:43][CH:44]=[CH:45][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:41]1([C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)[CH:42]=[CH:43][CH:44]=[CH:45][C:46]=1[C:24]1[CH:25]=[CH:26][C:27]2[N:40]=[C:31]3[C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][C:37]=4[CH:38]=[CH:39][N:30]3[C:28]=2[CH:29]=1

참가 물질

9

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 80271Tri-o-tolylphosphineHCID 4589187Biphenyl-2-boronic acidHCID 710778419-Bromobenzimidazo[2,1-a]isoquinoline

생성물 1

HCID 710779309-Biphenyl-2-ylbenzo[4,5]imidazo[2,1-a]isoquinoline

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 1140Toluene용매HCID 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 14.8 g (50 mmol) of 9-bromobenzimidazo[2,1-a]isoquinoline, 9.9 g (55 mmol) of 1,1′-biphenyl-2-boronic acid and 25.5 g (120 mmol) of tri-potassium 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 cooling, 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), three times with 100 ml of ethanol and finally dried. The residue is recrystallised from toluene. The yield is 17 g (45 mmol, 92%).

후처리

  1. temperaturethe mixture is subsequently heated
  2. temperatureunder reflux for 16 h
  3. temperatureAfter cooling
  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), three times with 100 ml of ethanol
  6. customfinally dried
  7. customThe residue is recrystallised from toluene

출처 및 근거

ORD 기록
ord-30f4b6e632154c02baa0cf9d66528242
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09118022B2

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