Nitrogen → [4'-(8,12b-Diazabenzo[a]aceanthrylen-8-yl)biphenyl-4-yl]diphenylamine

HRID 2277358

反応式

HRID 2277358 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH:27]1[C:32]2[N:33]3[C:46]4[C:45]([C:31]=2[CH:30]=[CH:29][CH:28]=1)=[CH:44][CH:43]=[CH:42][C:41]=4[NH:40][C:39]1[C:34]3=[CH:35][CH:36]=[CH:37][CH:38]=1.N#N.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.CC([O-])(C)C.[Na+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH:27]1[C:32]2[N:33]3[C:46]4[C:45]([C:31]=2[CH:30]=[CH:29][CH:28]=1)=[CH:44][CH:43]=[CH:42][C:41]=4[N:40]([C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[CH:10][CH:9]=2)=[CH:6][CH:7]=1)[C:39]1[C:34]3=[CH:35][CH:36]=[CH:37][CH:38]=1

参加物

9

反応物 5

HCID 947NitrogenHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 113155504-Bromo-4'-(diphenylamino)biphenylHCID 23676156Sodium t-butoxideHCID 671105678H-8,12b-Diazabenzo[a]aceanthrylene

生成物 1

HCID 67324186[4'-(8,12b-Diazabenzo[a]aceanthrylen-8-yl)biphenyl-4-yl]diphenylamine

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

A degassed solution of 35.6 g (89 mmol) of (4′-bromobiphenyl-4-yl)-diphenylamine and 22.0 g (81 mmol) of 8H-8,12b-diazabenzo[a]aceanthrylene in 1000 ml of dioxane is saturated with N2 for 1 h. Then firstly 1.0 ml (4 mmol) of P(tBu)3, then 0.4 g (2 mmol) of palladium(II) acetate are added to the solution, and 11.7 g (122 mmol) of NaOtBu in the solid state are subsequently added. The reaction mixture is heated under reflux for 18 h. After cooling to room temperature, 1000 ml of water are carefully added. The organic phase is separated off, washed with 4×50 ml of water and dried over MgSO4, and the solvent is removed in vacuo. The pure product is obtained by recrystallisation and final sublimation in a high vacuum.

後処理

  1. additionare subsequently added
  2. temperatureThe reaction mixture is heated
  3. temperatureunder reflux for 18 h
  4. customThe organic phase is separated off
  5. washwashed with 4×50 ml of water
  6. dry with materialdried over MgSO4
  7. customthe solvent is removed in vacuo
  8. customThe pure product is obtained by recrystallisation

出典と根拠

ORDレコード
ord-ecf6fc362d3a484090a4aaeee18f7bf1
出典データセット
uspto-grants-2015_09
特許番号
US09133119B2

関連ノート

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