Dimethyl Sulfoxide → HCID 178471780, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl trans-(4-{[(2-{[(3,5-bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-ethyl-amino]-methyl}-cyclohexyl)-acetate (which is prepared by treating the corresponding starting compound in a same manner as in Example 12 (1)-(3)) (2.6 g) is dissolved dimethylsulfoxide (15 ml), and thereto are added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium dichloromethane complex (73 mg), potassium acetate (977 mg) and bis(pinacolato)diboron (1.26 g), and the mixture is heated to 80° C. under nitrogen atmosphere and stirred for 2 hours. The reaction solution is cooled to room temperature and thereto are added a saturated brine and ethyl acetate, and the mixture is separated and the organic layer is washed with a saturated brine again, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is dissolved in tetrahydrofuran (30 ml) and thereto is added dropwise a 30% aqueous hydrogen peroxide solution (30 ml) under ice-cooling. The mixture is stirred for 1 hour, and thereto is added a saturated aqueous sodium thiosulfate solution to consume the excess hydrogen peroxide and thereto are added water and ethyl acetate, and the mixture is separated. The organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=19:1 to 7:3) to give ethyl trans-(4-{[(2-{[(3,5-bis-trifluoromethyl-benzyl)-(5-hydroxy-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-ethylamino]-methyl}-cyclohexyl)-acetate (1.29 g). MS (m/z): 721 [M+H]+

Provenance & Evidence