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

HRID 1242443

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+]>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.C1(C)C=CC=CC=1>[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

A solution of 0.84 g (1.2 mmol) bis(triphenylphosphine)palladium(II)chloride, 9.58 g (40 mmol) methyl 6-chloro-4-(trifluoromethyl)nicotinate and 10.08 g (52 mmol) of 4-(trifluoromethyl)benzeneboronic acid in 200 ml degassed toluene was treated with 40 ml aqueous 2M K3PO4 and heated at 80° C. for 16 h. The reaction was cooled to RT and extracted with H2O (0° C.)/Et2O (3x). The organic phases were washed with aqueous 10% NaCl, dried (NaSO4) and evaporated. Purification by flash-chromatography on silica gel (dichloromethane/heptane 2:1 to 1:1) gave 9.91 g of the title compound as an off-white powder.

Workup

temperatureThe reaction was cooled to RT
extractionextracted with H2O (0° C.)/Et2O (3x)
washThe organic phases were washed with aqueous 10% NaCl
dry with materialdried (NaSO4)
customevaporated
customPurification by flash-chromatography on silica gel (dichloromethane/heptane 2:1 to 1:1)

Sources & evidence

ORD record: ord-de3bc50f33be4802bc7fd4fe69c091e5
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115611B2

Linked notes

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