Sodium hydride → 4,7-bis(4-(N,N-diphenylamino)phenyl)-2-(6-cyanopyridin-3-yl)-2H-benzo[d][1,2,3]triazole

HRID 1050708Notes

Reaction equation

HRID 1050708 reaction equation
[H-].[Na+].[C:3]1([N:9]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[C:30]4[C:26](=[N:27][NH:28][N:29]=4)[C:25]([C:31]4[CH:36]=[CH:35][C:34]([N:37]([C:44]5[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=5)[C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)=[CH:33][CH:32]=4)=[CH:24][CH:23]=3)=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.F[C:51]1[CH:52]=[CH:53][C:54]([C:57]#[N:58])=[N:55][CH:56]=1>CN(C)C=O>[C:10]1([N:9]([C:16]2[CH:17]=[CH:18][C:19]([C:22]3[C:30]4[C:26](=[N:27][N:28]([C:51]5[CH:56]=[N:55][C:54]([C:57]#[N:58])=[CH:53][CH:52]=5)[N:29]=4)[C:25]([C:31]4[CH:36]=[CH:35][C:34]([N:37]([C:38]5[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=5)[C:44]5[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=5)=[CH:33][CH:32]=4)=[CH:24][CH:23]=3)=[CH:20][CH:21]=2)[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 113324532-Cyano-5-fluoropyridineHCID 866799124,7-bis(4-(N,N-diphenylamino)phenyl)-2H-benzo[d][1,2,3]triazole

Product 1

HCID 866799234,7-bis(4-(N,N-diphenylamino)phenyl)-2-(6-cyanopyridin-3-yl)-2H-benzo[d][1,2,3]triazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Sodium hydride (60%, 120 mg, 3 mmol) was added to a solution of Intermediate P (1.21 g, 2.0 mmol) and 5-fluoro-2-pyridinecarbonitrile (0.61 g, 5.0 mmol) in anhydrous dimethylformamide (20 mL), stirred under argon, and the obtained mixture was heated at 80° C. for 16 hours. The reaction mixture was poured into ice/water (200 mL), and extracted with dichloromethane (200 mL). The extract was dried over sodium sulfate, and the solvent was evaporated. The residue was diluted with chlorobenzene (50 mL), and the volatiles were removed under high vacuum. The crude product was purified by chromatography (dichloromethane/hexane 2:1) to give 4,7-bis(4-(N,N-diphenylamino)phenyl)-2-(6-cyanopyridin-3-yl)-2H-benzo[d][1,2,3]triazole, dark-red crystals, 1.20 g (85%).

Workup

  1. extractionextracted with dichloromethane (200 mL)
  2. dry with materialThe extract was dried over sodium sulfate
  3. customthe solvent was evaporated
  4. additionThe residue was diluted with chlorobenzene (50 mL)
  5. customthe volatiles were removed under high vacuum
  6. customThe crude product was purified by chromatography (dichloromethane/hexane 2:1)

Sources & evidence

ORD record
ord-c247e9d7d4ac480bb82b47a1217157c6
Source dataset
uspto-grants-2016_07
Patent number
US09382424B2

Reaction notes

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