[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([OH:33])[CH2:15][C:16]2[C:21](Cl)=[CH:20][N:19]=[C:18]([C:23]3[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=3)[N:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(P(C(C)(C)C)C1C=CC2C(=CC=CC=2)C=1C1C2C(=CC=CC=2)C=CC=1)(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]2[O:33][C:21]3[CH:20]=[N:19][C:18]([C:23]4[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=4)=[N:17][C:16]=3[CH2:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]A mixture of 4-{2-[5-chloro-2-(4-methanesulfonyl-phenyl)-pyrimidin-4-yl]-1-hydroxy-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (50 mg), palladium acetate (3 mg), racemic 2-(di-tert-butylphosphino)-1,1′-binapthyl (6 mg), and cesium carbonate (50 mg) in toluene (1 mL) is heated in an oil bath at 70° C. under an argon atmosphere for 6 h. After cooling to room temperature ethyl acetate is added and the organic phase is separated, washed with water and brine, dried over MgSO4, and concentrated in vacuo. The residue is chromatographed on silica gel [dichloromethane/(dichloromethane/methanol/NH4OH 24:24:1) 96:4→90:10]. The crude product is triturated with diethyl ether, filtered off, and dried to give the title compound. LC (method 7): tR=1.44 min; Mass spectrum (ESI+): m/z=460 [M+H]+.
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