Pivalic acid → 12,12-Dimethyl-7-phenyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene

HRID 2275918ノート

反応式

HRID 2275918 の反応式
C(O)(=O)C(C)(C)C.[C:8]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:13]=[CH:12][C:11]([NH:14][C:15]2[CH:27]=[CH:26][C:25]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:18]([CH3:29])([CH3:28])[C:17]=3[CH:16]=2)=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+].C([O-])([O-])=O.[Na+].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.ClCCl>[CH3:28][C:18]1([CH3:29])[C:17]2=[CH:16][C:15]3[NH:14][C:11]4[C:12]([C:27]=3[CH:26]=[C:25]2[C:24]2[C:19]1=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:13][C:8]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[CH:9][CH:10]=4

参加物

7

反応物 4

HCID 6417Pivalic acidHCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 20730584N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amine

生成物 1

HCID 6679746212,12-Dimethyl-7-phenyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒2 回HCID 6344Dichloromethane溶媒

反応条件

温度
120 °C

実験手順

50 ml of pivalic acid are added to 20 g of biphenyl-4-yl-(9,9-dimethyl-9H-fluoren-2-yl)amine (55.3 mmol), 1.2 g of palladium(II)acetate (5.5 mmol) and 0.8 g of potassium carbonate (5.5 mmol), and the mixture is stirred at 120° C. for 9 h. After this time, 1.2 g of palladium(II)acetate (5.5 mmol) are added, and the mixture is stirred at 120° C. for a further 9 h. 300 ml of dichloromethane and 0.1 M Na2CO3 solution are then added. The mixture is partitioned between water and dichloromethane, the aqueous phase is extracted three times with dichloromethane, and the combined organic phases are dried over Na2SO4 and evaporated in a rotary evaporator. The residue is recrystallised from toluene/heptane. The yield is 10 g (27.7 mmol, 50%).

後処理

  1. stirringthe mixture is stirred at 120° C. for a further 9 h
  2. customThe mixture is partitioned between water and dichloromethane
  3. extractionthe aqueous phase is extracted three times with dichloromethane
  4. dry with materialthe combined organic phases are dried over Na2SO4
  5. customevaporated in a rotary evaporator
  6. customThe residue is recrystallised from toluene/heptane

出典と根拠

ORDレコード
ord-d483eccad8b84a3ba45ccad44cd9732d
出典データセット
uspto-grants-2015_09
特許番号
US09126970B2

反応ノート

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