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

HRID 2275918Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2275918
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

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysator2×HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d483eccad8b84a3ba45ccad44cd9732d
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09126970B2

Notizen zur Reaktion

Wird geladen…