HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Sodium Carbonate → 7-(4,6-Diphenylpyrimidin-2-yl)-10-(4,6-diphenyl-1,3,5-triazin-2-yl)-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene

HRID 2275927
Notes
Print preview

Reaction equation

HRID 2275927 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([C:15]1[N:20]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:18]=[C:17]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:16]=1)[C:10]1[CH:9]=[C:8]3[C:33]([CH3:41])([CH3:40])[C:34]4[C:39]([C:7]3=[CH:6][C:5]2=1)=[CH:38][CH:37]=[CH:36][CH:35]=4.B1(B2O[C:54]([CH3:57])(C)[C:53]([CH3:59])([CH3:58])O2)OC(C)(C)C(C)(C)O1.[C:60]([O-])(=O)[CH3:61].[K+].C1(C2N=C(C3C=CC=CC=3)N=C(N3C4C=C5C(C)(C)C6C(C5=CC=4C4C3=CC=C(B3OC(C)(C)C(C)(C)O3)C=4)=CC=CC=6)N=2)C=CC=CC=1.Cl[C:115]1[N:120]=C(C2C=CC=CC=2)[CH:118]=[C:117]([C:127]2[CH:132]=[CH:131][CH:130]=[CH:129][CH:128]=2)[N:116]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C1(C)C=CC=CC=1.C(Cl)Cl>[C:127]1([C:117]2[CH:118]=[C:59]([C:53]3[CH:54]=[CH:57][CH:61]=[CH:60][CH:58]=3)[N:120]=[C:115]([C:2]3[CH:3]=[C:4]4[C:12](=[CH:13][CH:14]=3)[N:11]([C:15]3[N:20]=[C:19]([C:21]5[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=5)[N:18]=[C:17]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[N:16]=3)[C:10]3[CH:9]=[C:8]5[C:33]([CH3:41])([CH3:40])[C:34]6[C:39]([C:7]5=[CH:6][C:5]4=3)=[CH:38][CH:37]=[CH:36][CH:35]=6)[N:116]=2)[CH:132]=[CH:131][CH:130]=[CH:129][CH:128]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

12

Reactant 6

HCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 18047392-Chloro-4,6-diphenylpyrimidineHCID 2733548Bis(pinacolato)diboraneHCID 667979517-Bromo-10-(4,6-diphenyl-1,3,5-triazin-2-yl)-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene
HCID 66797982
10-(4,6-Diphenyl-1,3,5-triazin-2-yl)-12,12-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10,12-dihydro-10-azaindeno[2,1-b]fluorene

Product 1

HCID 667980427-(4,6-Diphenylpyrimidin-2-yl)-10-(4,6-diphenyl-1,3,5-triazin-2-yl)-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene

Reagents, catalysts & solvents 5

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent2×

Procedure

40 g (67.4 mmol) of 7-bromo-10-(4,6-diphenyl-1,3,5-triazin-2-yl)-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene, 17.1 g (67.4 mmol) of bis(pinacolato)diborane and 19.8 g of potassium acetate are suspended in 700 ml of dioxane. 2.8 g (3.4 mmol) of 1,1-bis(diphenylphosphino)ferrocenepalladium(II) dichloride complex with DCM are added to this suspension. The reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is separated off, washed three times with 200 ml of water and subsequently evaporated to dryness. The residue is recrystallised from toluene. 30 g (46.8 mmol) of 10-(4,6-diphenyl-1,3,5-triazin-2-yl)-12,12-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10,12-dihydro-10-azaindeno[2,1-b]fluorene, 11.2 g (42.15 mmol) of 2-chloro-4,6-diphenylpyrimidine and 9.9 g of sodium carbonate are suspended in 300 ml of dioxane, 300 ml of toluene and 100 ml of water. 2.7 g (2.3 mmol) of Pd(PPh3)4 are added to this suspension. The reaction mixture is heated under reflux for 5 h. After cooling, the precipitated solid is filtered off with suction, washed with water and ethanol and dried. The residue is extracted with hot toluene, recrystallised from toluene and finally sublimed in a high vacuum, the purity is 99.9%. Yield: 18 g, 59% 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. washwashed three times with 200 ml of water
  6. customsubsequently evaporated to dryness
  7. customThe residue is recrystallised from toluene
  8. temperatureThe reaction mixture is heated
  9. temperatureunder reflux for 5 h
  10. temperatureAfter cooling
  11. filtrationthe precipitated solid is filtered off with suction
  12. washwashed with water and ethanol
  13. customdried
  14. extractionThe residue is extracted with hot toluene
  15. customrecrystallised from toluene

Sources & evidence

ORD record
ord-6a763b0eb6de45fe811fd7b953e1d8af
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09126970B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes