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

HRID 2275918Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

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%).

Workup

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

Sources & evidence

ORD record: ord-d483eccad8b84a3ba45ccad44cd9732d
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126970B2

Reaction notes

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