Br[C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[CH2:5][N:6]1[C:10]([CH3:11])=[CH:9][C:8]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[N:13]=2)=[N:7]1.[OH:31][CH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:11][C:10]1[N:6]([CH2:5][C:4]2[CH:3]=[C:2]([N:35]3[CH2:36][CH2:37][CH:32]([OH:31])[CH2:33][CH2:34]3)[CH:30]=[CH:29][CH:28]=2)[N:7]=[C:8]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[N:13]=2)[CH:9]=1A mixture of 150 mg (0.313 mmol) of the compound from Example 1A, 63 mg (0.626 mmol) of 4-hydroxypiperidine, 19 mg (0.021 mmol) of tris(dibenzylideneacetone)dipalladium(0), 30 mg (0.063 mmol) of 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (X-Phos) and 254 mg (0.782 mmol) of caesium carbonate in 3 ml of anhydrous DMF was stirred at 80° C. under argon for 12 h. After cooling to RT, the reaction mixture was filtered through a little Celite and the filtrate was then separated into its components by means of preparative HPLC (method 11). After concentration of the product fractions and drying under high vacuum, 36 mg (23% of theory) of the title compound were obtained.
Loading…