I[C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[CH:5]=[CH:6][C:7]=1[OH:8].[N+:19]([C:22]1[C:26](B2OC(C)(C)C(C)(C)O2)=[CH:25][N:24]([CH:36]2[CH2:41][CH2:40][CH2:39][CH2:38][O:37]2)[N:23]=1)([O-:21])=[O:20].[F-].[K+]>O1CCCC1.C(P([Pd-2]P(C(C)(C)C)(C(C)(C)C)C(C)(C)C)(C(C)(C)C)C(C)(C)C)(C)(C)C>[N+:19]([C:22]1[C:26]([C:2]2[CH:3]=[C:4]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=3)[CH:5]=[CH:6][C:7]=2[OH:8])=[CH:25][N:24]([CH:36]2[CH2:41][CH2:40][CH2:39][CH2:38][O:37]2)[N:23]=1)([O-:21])=[O:20]A mixture of 3-iodo-3′-(trifluoromethyl)biphenyl-4-ol (Preparation 2, 0.5 g, 1.3 mmol), 3-nitro-1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.42 g, 1.3 mmol), potassium fluoride (0.39 g, 0.65 mmol) in tetrahydrofuran (10 mL) was degassed. Bis-(tri-t-Butylphosphino)palladium (0) (35 mg, 0.068 mmol) was added and the reaction heated at 65° C. for 4 hours. After cooling the solvent was removed in vacuo and the residue was purified by silica gel chromatography (ethyl acetate:heptane 1:10) to provide the title compound (0.34 g, 61%) as a colourless oil.
Wird geladen…