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With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,4-dioxane; water; at 90℃; for 3h;Inert atmosphere;
To a solution of <strong>[685892-23-3]methyl 2-bromo-6-chlorobenzoate</strong> (520 mg, 2.00 mmol) and 1-cyclohexenylboronic acid pinacol ester (500 mg, 2.40 mmol) in 10 mL of dioxane and 2 mL of water under nitrogen was added sodium carbonate (500 mg, 4.60 mmol) and Pd(dppf)Cl2 (10 mg), and the resulting mixture was stirred at 90 C for 3 hrs. The mixture was concentrated and the residue was purified on silica gel by column chromatography(petroleum as eluent) to give the title compound (520 mg, 100%) as colorless oil. LCMS (ESI) calc?d for C14H15ClO2 [M+H]+: 251, found: 251.
6-chloro-3-(cyclohex-1-en-1-yl)imidazo[1,2-a]pyridine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
83%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In 1,4-dioxane; water; at 50.0℃; for 5.0h;Inert atmosphere;
General procedure: To an oven dried 5 mL microwave vessel was addedPd(dppf)Cl2·CH2Cl2 (4 mol%), halide/pseudohalide (1 equiv),boron coupling partner (1 equiv), and Cs2CO3 (3 equiv). Thevessel was then capped and purged with N2 before addition ofCyrene (1 mL, 0.25 M) and H2O (1.8 mL). The reaction mixturewas heated to 50 C and maintained at this temperature withstirring for 5 h before the vessel was vented and decapped. Thesolution was then diluted with Et2O (10 mL) and washed withwater (2 × 20 mL) and brine (2 × 20 mL). The organics were thenpassed through a hydrophobic frit and concentrated underreduced pressure to give a residue, which was purified by flashchromatography (silica gel) to afford the title compound.
62%
With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; isosorbide dimethyl ether; In water; at 60.0℃; for 1.0h;Microwave irradiation; Inert atmosphere;
General procedure: To an oven-dried 5 mL microwave vessel was addedPd(dppf)Cl2·CH2Cl2 (4 mol%), aryl halide/pseudohalide (1equiv.), organoboron (1 equiv.), and K3PO4 (3 equiv.). The vesselwas then capped and purged with N2 before addition of DMI (1mL, 0.25 M) and H2O (5 equiv.). The reaction mixture washeated to 60 C and maintained at this temperature with stirringfor 1 h before the vessel was vented and decapped. Thesolution was then diluted with EtOAc (10 mL) and washed withwater (2 × 20 mL) and brine (2 × 20 mL). The organics were thenpassed through a hydrophobic frit and concentrated underreduced pressure to give a residue, which was purified by flashchromatography (silica gel) to afford the product.
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