Potassium Phosphate, Tribasic → 3-Pyridinecarboxylic acid,4-(trifluoromethyl)-6-[4-(trifluoromethyl)phenyl]-,methyl ester

HRID 890465

Reaction equation

Cl[C:2]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[F:16][C:17]([F:28])([F:27])[C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:9][O:8][C:6](=[O:7])[C:5]1[C:10]([C:12]([F:15])([F:14])[F:13])=[CH:11][C:2]([C:21]2[CH:22]=[CH:23][C:18]([C:17]([F:28])([F:27])[F:16])=[CH:19][CH:20]=2)=[N:3][CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of bis(triphenylphosphine)palladium(II)chloride (0.84 g, 1.2 mmol), methyl 6-chloro-4-(trifluoromethyl)nicotinate (9.58 g, 40 mmol) and 4-(trifluoromethyl) benzene boronic acid (10.1 g, 52 mmol) in degassed toluene (200 ml) was added aqueous 2 M K3PO4 (40 ml). The suspension was stirred at 80° C. for 16 h. The reaction mixture was cooled to RT, ice water was added and the mixture was extracted three times with diethyl ether. The organic phases were washed with aqueous 10% NaCl, dried (Na2SO4) and evaporated. Purification by flash-chromatography on silica gel (dichloromethane/heptane 2:1 to 1:1) gave 9.91 g (28.3 mmol, 71%) of the title compound as off-white powder.

Workup

temperatureThe reaction mixture was cooled to RT
extractionthe mixture was extracted three times with diethyl ether
washThe organic phases were washed with aqueous 10% NaCl
dry with materialdried (Na2SO4)
customevaporated
customPurification by flash-chromatography on silica gel (dichloromethane/heptane 2:1 to 1:1)

Sources & evidence

ORD record: ord-8a7206d3d114428ebd1a9fdc3e993cb6
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06995263B2

Linked notes

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