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

HRID 2275918노트

반응식

HRID 2275918 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매2회HCID 6344Dichloromethane용매

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온도
120 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-d483eccad8b84a3ba45ccad44cd9732d
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09126970B2

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