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2-Chloro-4,6-diphenyl-1,3,5-triazine → 6-(4,6-Diphenyl-1,3,5-triazin-2-yl)-8,8-dimethyl-8H-indolo[3,2,1-de]acridine

HRID 1627748
Notes
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Reaction equation

HRID 1627748 reaction equation
[CH3:1][C:2]1([CH3:25])[C:15]2[C:10]3=[C:11]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=4[N:9]3[C:8]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=3)[CH:12]=[C:13](B(O)O)[CH:14]=2.Cl[C:27]1[N:32]=[C:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:30]=[C:29]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[N:28]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.O1CCOCC1>[C:39]1([C:29]2[N:30]=[C:31]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[N:32]=[C:27]([C:5]3[CH:4]=[C:3]4[C:8]5=[C:7]([C:23]6[CH:22]=[CH:21][CH:20]=[CH:19][C:24]=6[N:9]5[C:10]5[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=5[C:2]4([CH3:25])[CH3:1])[CH:6]=3)[N:28]=2)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 196982-Chloro-4,6-diphenyl-1,3,5-triazineHCID 62657Potassium Phosphate, TribasicHCID 80271Tri-o-tolylphosphineHCID 673261988,8-Dimethyl-8H-indolo[3,2,1-de]acridine-6-boronic acid

Product 1

HCID 680145136-(4,6-Diphenyl-1,3,5-triazin-2-yl)-8,8-dimethyl-8H-indolo[3,2,1-de]acridine

Reagents, catalysts & solvents

4
HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

36 g (110.0 mmol) of 8,8-dimethyl-8H-indolo[3,2,1-de]acridine-6-boronic acid, 29.5 g (110.0 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine and 44.6 g (210.0 mmol) of tripotassium phosphate are suspended in 500 ml of toluene, 500 ml of dioxane and 500 ml of water. 913 mg (3.0 mmol) of tri-o-tolylphosphine and then 112 mg (0.5 mmol) of palladium (II) acetate are added to this suspension, and the reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is separated off, filtered through silica gel, washed three times with 200 ml of water and subsequently evaporated to dryness. The residue is recrystallised from toluene and from dichloromethane/isopropanol and finally sublimed in a high vacuum, the purity is 99.9%. The yield is 46 g (89 mmol), corresponding to 83% of theory.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 16 h
  3. temperatureAfter cooling
  4. customthe organic phase is separated off
  5. filtrationfiltered through silica gel
  6. washwashed three times with 200 ml of water
  7. customsubsequently evaporated to dryness
  8. customThe residue is recrystallised from toluene and from dichloromethane/isopropanol

Sources & evidence

ORD record
ord-a6770a7d366e4c6b95e63f56fa609ed3
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08785636B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes