Sodium hydride → 10-(4,6-Bis[1,1';3',1'']terphenyl-5'-yl-1,3,5-triazin-2-yl)-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene

HRID 2275930Notes

Reaction equation

HRID 2275930 reaction equation
[CH3:1][C:2]1([CH3:22])[C:10]2=[CH:11][C:12]3[NH:13][C:14]4[C:19]([C:20]=3[CH:21]=[C:9]2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:18][CH:17]=[CH:16][CH:15]=4.[H-].[Na+].Cl[C:26]1[N:31]=[C:30]([C:32]2[CH:33]=[C:34]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[CH:35]=[C:36]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH:37]=2)[N:29]=[C:28]([C:50]2[CH:51]=[C:52]([C:62]3[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=3)[CH:53]=[C:54]([C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=3)[CH:55]=2)[N:27]=1>CN(C)C=O>[C:62]1([C:52]2[CH:51]=[C:50]([C:28]3[N:29]=[C:30]([C:32]4[CH:37]=[C:36]([C:38]5[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=5)[CH:35]=[C:34]([C:44]5[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=5)[CH:33]=4)[N:31]=[C:26]([N:13]4[C:12]5[CH:11]=[C:10]6[C:2]([CH3:22])([CH3:1])[C:3]7[C:8]([C:9]6=[CH:21][C:20]=5[C:19]5[C:14]4=[CH:15][CH:16]=[CH:17][CH:18]=5)=[CH:7][CH:6]=[CH:5][CH:4]=7)[N:27]=3)[CH:55]=[C:54]([C:56]3[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=3)[CH:53]=2)[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 582991192,4-Di([1,1':3',1''-terphenyl]-5'-yl)-6-chloro-1,3,5-triazineHCID 665852047,7-Dimethyl-5,7-dihydroindeno[2,1-b]carbazole

Product 1

HCID 6679787010-(4,6-Bis[1,1';3',1'']terphenyl-5'-yl-1,3,5-triazin-2-yl)-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

11.3 g (40 mmol) of 12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]-fluorene are dissolved in 285 ml of dimethylformamide under a protective-gas atmosphere, and 1.9 g of 60% NaH in mineral oil (19 mmol) are added. After 1 h at room temperature, a solution of 2-chloro-4,6-bis-[1,1′;3′,1″]terphenyl-5′-yl-1,3,5-triazine (25.1 g, 44 mmol) in 315 ml of dimethylformamide is added dropwise. The reaction mixture is stirred at room temperature for 12 h. After this time, the reaction mixture is poured onto ice and extracted three times with dichloromethane. The combined organic phases are dried over Na2SO4 and evaporated. The residue is extracted with hot toluene. The yield is 23 g (28 mmol, 70%).

Workup

  1. additionare added
  2. additionAfter this time, the reaction mixture is poured onto ice
  3. extractionextracted three times with dichloromethane
  4. dry with materialThe combined organic phases are dried over Na2SO4
  5. customevaporated
  6. extractionThe residue is extracted with hot toluene

Sources & evidence

ORD record
ord-95855c69c19f42c99ebb511f4ab626fa
Source dataset
uspto-grants-2015_09
Patent number
US09126970B2

Reaction notes

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