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With caesium carbonate;palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 100℃; for 0.916667h;Inert atmosphere; Microwave irradiation;
Example 1805-[4-(l-[(3S)-l-(Cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-6-fluoro-lH- benzimidazol-2-yl)phenyl] -lH-indazole(a) 1,1-Dimethylethyl (3S)-3-[(5-fluoro-2-nitrophenyl)amino]methyl}-l- pyrrolidinecarboxylate2-Chloro-4-fluoro-l -nitrobenzene (1.8 g, 10.25 mmol). 1,1-dimethylethyl (3S)-3- (aminomethyl)-l -pyrrolidmecarboxylate (2.7 g, 13.48 mmol) Cs2C03 (4.8 g, 14.73 mmol), Pd(OAc)2 (.126 g, 0.561 mmol) and BINAP (.59 g, 0.948 mmol) were suspended in toluene (16 mL) in a microwave vial under nitrogen. The reaction mixture was heated in a microwave reactor at 100 C for 45 min. An additional aliquot Pd Pd(OAc)2 (~ 100 mg) was added and the reaction heated an additional 10 min in the microwave reactor. The reaction mixture was filter and partitioned between EtOAc and aqueous NaHC03. The EtOAc layer was washed with brine, dry over sodium sulfate, filtered, and evaporated to dryness. The crude 1,1-dimethylethyl (3S)-3-[(5-fluoro-2-nitrophenyl)amino]methyl}-l- pyrrolidinecarboxylate was purified by silica gel column chromatography using a gradient of 0-10% IPA/EtOAc and used without further characterization.
With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 70℃;Inert atmosphere;
Example 108 l-[(3S)-l-(Cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-7-methyl-2-[4'-(methyloxy)- 4-biphenylyl]-lH-benzimidazole(a) 1,1-Dimethylethyl (35)-3-[(2-methyl-6-nitrophenyl)amino]methyl}-l- pyrrolidinecarboxylate2-Fluoro-3-nitrotoluene (5 g) was dissolved in 30 mL dry DMSO. To this was added DIEA (5.80 g) and 1,1-dimethylethyl (3S)-3-(aminomethyl)-l-pyrrolidinecarboxylate (3.49 g). The reaction flask was flushed with nitrogen and the reaction mixture stirred at 70 °C overnight. After cooling, the reaction mixture was diluted with EtOAc and washed with brine. The EtOAc layer was dried and the solvent removed by evaporation. The crude product was purified by silica gel column chromatography using petroleum ether / EtOAc to afford the titled compound.
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