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

HRID 523450

Reaction equation

HRID 523450 reaction equation
[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

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e7ed437354c74910853f4256e480fb4c
Source dataset
uspto-grants-2016_05
Patent number
US09337430B2

Linked notes

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