Pivalic acid → HCID 66797983, compound

HRID 2275932Notes

Reaction equation

C(O)(=O)C(C)(C)C.[CH3:8][C:9]1([CH3:29])[C:21]2[CH:20]=[C:19]([NH:22][C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)[CH:18]=[CH:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2.C(=O)([O-])[O-].[K+].[K+].C([O-])([O-])=O.[Na+].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.ClCCl>[CH3:8][C:9]1([CH3:29])[C:21]2[CH:20]=[C:19]3[NH:22][C:23]4[C:28]([C:18]3=[CH:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:27][N:26]=[CH:25][CH:24]=4

Participants

Conditions

Temperature: 120 °C

Procedure

70 ml of pivalic acid are added to 30 g of (9,9-dimethyl-9H-fluoren-2-yl)pyridin-4-ylamine (105 mmol), 2.35 g of palladium(II)acetate (10.5 mmol) and 1.44 g of potassium carbonate (10.5 mmol), and the mixture is stirred at 120° C. for 9 h. After this time, 2.35 g of palladium(II)acetate (10.5 mmol) are added, and the mixture is stirred at 120° C. for a further 9 h. 200 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, the combined organic phases are dried over Na2SO4 and evaporated in a rotary evaporator. The residue is recrystallised from toluene/heptane. The yield is 13.4 g (13.5 mmol, 45%).

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-56cdbac0cf8e4b2589f752eaaaec7787
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126970B2

Reaction notes

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