Toluene → HCID 87157125, compound

HRID 2275949Notes

Reaction equation

HRID 2275949 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]3[C:19](=[CH:20][CH:21]=2)[N:18]([C:22]2[CH:27]=[CH:26][C:25]([C:28]4[CH:33]=[CH:32][C:31]([N:34]5[C:46]6[CH:45]=[C:44]7[C:47]([CH3:55])([CH3:54])[C:48]8[C:53]([C:43]7=[CH:42][C:41]=6C6C5=CC=CC=6)=[CH:52][CH:51]=[CH:50][CH:49]=8)=[CH:30][CH:29]=4)=[CH:24][CH:23]=2)[C:17]2[CH:16]=[C:15]4[C:56]([CH3:64])([CH3:63])[C:57]5[C:62]([C:14]4=[CH:13][C:12]3=2)=[CH:61][CH:60]=[CH:59][CH:58]=5)O1.Cl[C:67]1[N:72]=[C:71]([C:73]2[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=2)[N:70]=[C:69]([C:79]2[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=2)[N:68]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:91]1(C)[CH:96]=[CH:95][CH:94]=[CH:93][CH:92]=1>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>[C:91]1([C:67]2[N:72]=[C:71]([C:73]3[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=3)[N:70]=[C:69]([C:79]3[CH:84]=[C:83]4[C:82](=[CH:81][CH:80]=3)[N:34]([C:31]3[CH:30]=[CH:29][C:28]([C:25]5[CH:24]=[CH:23][C:22]([N:18]6[C:17]7[CH:16]=[C:15]8[C:56]([CH3:63])([CH3:64])[C:57]9[C:62]([C:14]8=[CH:13][C:12]=7[C:11]7[C:19]6=[CH:20][CH:21]=[CH:9][CH:10]=7)=[CH:61][CH:60]=[CH:59][CH:58]=9)=[CH:27][CH:26]=5)=[CH:33][CH:32]=3)[C:46]3[CH:45]=[C:44]5[C:47]([CH3:55])([CH3:54])[C:48]6[C:53]([C:43]5=[CH:42][C:41]4=3)=[CH:52][CH:51]=[CH:50][CH:49]=6)[N:68]=2)[CH:96]=[CH:95][CH:94]=[CH:93][CH:92]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 196982-Chloro-4,6-diphenyl-1,3,5-triazineHCID 66797840HCID 66797840, compound

Product 1

HCID 87157125HCID 87157125, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

6.0 g (7.0 mmol) of 4-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluoren-10-yl)-4′-(12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluoren-10-yl)biphenyl, 1.9 g (7.1 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine and 0.83 g (7.8 mmol) of sodium carbonate are suspended in 400 ml of dioxane, 400 ml of toluene and 200 ml of water. 0.42 g (3.6 mmol) of Pd(PPh3)4 is 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 yield after sublimation is 5.2 g (5 mmol, 77%) with a purity of 99.9%.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 5 h
  3. temperatureAfter cooling
  4. filtrationthe precipitated solid is filtered off with suction
  5. washwashed with water and ethanol
  6. customdried
  7. extractionThe residue is extracted with hot toluene
  8. customrecrystallised from toluene
  9. customThe yield after sublimation

Sources & evidence

ORD record
ord-b066915afb2e4b588691bbe2ffe14853
Source dataset
uspto-grants-2015_09
Patent number
US09126970B2

Reaction notes

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