反应详情

温度

95 °C

(R)-3-Methylbutan-2-yl 4-(4-bromophenyl)-1-methyl-1H-1,2,3-triazol-5-ylcarbamate (101.4 mg. 0.28 mmol), methyl 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropanecarboxylate (108 mg, 0.36 mmol), X-Phos (39.5 mg, 0.083 mmol), palladium acetate (9.3 mg, 0.041 mmol), and potassium phosphate tribasic (176 mg, 0.83 mmol) were combined in toluene (6 mL). To this mixture was added degassed water (1.5 mL) and the mixture was stirred at 95° C. for 2 hrs until it became black. LC/MS indicated no more starting material. The mixture was extracted with ethyl acetate and water. The organic layer was washed with brine and dried. Solvents were evaporated and the residue was purified by ISCO flash column chromatography (12 g silica gel, 5% to 65% ethyl acetate in hexanes) to give a pale yellow solid as 1-{4′-[5-((R)-1,2-dimethyl-propoxycarbonylamino)-1-methyl-1H-[1,2,3]triazol-4-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid methyl ester (97.8 mg, 76.6% yield). LC/MS calcd for C26H30N4O4 (m/e) 462, obsd 463.2 (M+H).

1. additionTo this mixture was added
2. customdegassed water (1.5 mL)
3. extractionThe mixture was extracted with ethyl acetate and water
4. washThe organic layer was washed with brine
5. customdried
6. customSolvents were evaporated
7. customthe residue was purified by ISCO flash column chromatography (12 g silica gel, 5% to 65% ethyl acetate in hexanes)