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With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,4-dioxane; water at 100℃; for 2h;
2.55 4.2.55 Suzuki-Miyaura coupling: typical procedures.
General procedure: To a solution of 20b (51.5 mg, 0.118 mmol) in dioxane (1.0 mL) and water (0.5 mL) was added 3-methoxyphenylboronic acid (26.9 mg, 0.127 mmol), potassium carbonate (48.9 mg, 0.354 mmol), dichlorobis(triphenylphosphine)palladium (4.1 mg, 0.0059 mmol), and the mixture was heated at 100 °C for 2 h. The reaction mixture was partitioned between AcOEt and water. The organic layer was washed water, brine, dried with Na2SO4, and evaporated.
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane for 2h; Heating;
4.2. General method for preparation of compounds 6a-r, (exemplified by 6a)
General procedure: The building block 4 (100.0 mg, 0.21 mmol) was dissolved in dioxane (5 mL), then followed by the additions of 2-fluoro-3-methoxyphenylboronic acid (71.4 mg, 0.42 mmol), Pd(dppf)Cl2(20 mg), and Na2CO3 (66.8 mg, 0.63 mmol). The reaction mixture was heated at 100 C for 2 h before cooled to rt. After concentrated,the residue was dissolved in EtOAc (50 mL) and washed with H2O(10 mL 2), and brine (10 mL 2), dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel using petroleum ether-EtOAc (4:1) to give 6a (76.0 mg,69.9%) as a white solid.
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; toluene; acetonitrile at 110℃; for 60h; Inert atmosphere;
4 AMBMP analog 5 was synthesized according to scheme I.
4.6- dichloropyrimidine-2-amine was reacted with equivalent amount of benzo[d][l,3]dioxol-5- ylmethanamine in t-butanol. The reaction product was further reacted with equivalent amount of (3-( propoxy)phenyl)boronic acid, in the presence of Pd(PPh3)4 in a column. The product obtained was subjected to purification using silica gel chromatography on Combiflash Rf 200 by employing hexane-EtOAc step gradient (95:5 80:20) over 30 min. Fractions corresponding to the product peak were combined and concentrated using rotavap to afford AMBMP analog 5 in 48% yield. The product was characterized by NMR.
With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In lithium hydroxide monohydrate; toluene at 100℃; Schlenk technique; Inert atmosphere;