6(5H)-Phenanthridinone → 5-[3-(4,6-Diphenyl-1,3,5-triazin-2-yl)phenyl]-5H-phenanthridin-6-one

HRID 523450

반응식

HRID 523450 반응식
[CH:1]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:15])[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.Br[C:17]1[CH:18]=[C:19]([C:23]2[N:28]=[C:27]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:26]=[C:25]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[N:24]=2)[CH:20]=[CH:21][CH:22]=1.N1C=CC=CC=1C(=O)CC(C1C=CC=CN=1)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O.[Cu](I)I>[C:35]1([C:25]2[N:24]=[C:23]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:17][CH:18]=3)[N:28]=[C:27]([C:29]3[CH:34]=[C:33]([N:6]4[C:7](=[O:15])[C:8]5[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=5)[C:14]5[CH:1]=[CH:2][CH:3]=[CH:4][C:5]4=5)[CH:32]=[CH:31][CH:30]=3)[N:26]=2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

참가 물질

8

반응물 4

HCID 18536(5H)-PhenanthridinoneHCID 11430Potassium CarbonateHCID 27284941,3-Di(2-pyridyl)-1,3-propanedioneHCID 589433022-(3-Bromophenyl)-4,6-diphenyl-1,3,5-triazine

생성물 1

HCID 867326655-[3-(4,6-Diphenyl-1,3,5-triazin-2-yl)phenyl]-5H-phenanthridin-6-one

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

20 g (102 4 mmol) of 5H-phenanthridin-6-one, 43 g (112 mmol) of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine, 2.3 g (10 2 mmol) of 1,3-bis[2-pyridyl]-1,3-propanedione, 28.3 g (204 mmol) of potassium carbonate and 1.9 g (10.2) of copper iodide are stirred under reflux in 1000 ml of DMF for 90 h. The solution is diluted with water and extracted twice with ethyl acetate, the combined organic phases are dried over Na2SO4, evaporated in a rotary evaporator and purified by chromatography (EtOAc/hexane: 2/3). The residue is recrystallised from toluene and from dichloromethane and finally sublimed in a high vacuum, purity is 99.9%. The yield is 31 g (62 mmol), corresponding to 61% of theory.

후처리

  1. extractionextracted twice with ethyl acetate
  2. dry with materialthe combined organic phases are dried over Na2SO4
  3. customevaporated in a rotary evaporator
  4. custompurified by chromatography (EtOAc/hexane: 2/3)
  5. customThe residue is recrystallised from toluene and from dichloromethane

출처 및 근거

ORD 기록
ord-e7ed437354c74910853f4256e480fb4c
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09337430B2

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