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With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 12h;Reflux;
Compound (2-nitro-3-yl) boronic acid ((2-nitropyridin-3-yl) boronic acid, 10g, 59.9mmol), 1- hydroxy-8-bromo-naphthalene (1-Hydroxy-8-bromonaphthalene , 20.0g, 89.8mmol), tetrakis (triphenylphosphine) palladium (0) (3.5g, 3.0mmol), 2M K2CO3 solution (70ml), toluene (200ml), was added after the ethanol (100ml) for 12 hours by refluxing. After completion of the reaction to cool to room temperature and extracted with distilled water and ethyl acetate (EA). The organic layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation of dichloromethane and hexane and the objective compound as a developing solvent and purified by column chromatographyTo give a water-26-5 (14.5g, 91percent).
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 12h;Reflux;
Compound (3-nitro-pyridin-2-yl) boronic acid ((3-nitropyridin-2-yl) boronic acid, 10g, 59.9mmol), 1- hydroxy-8-bromo-naphthalene (1-Hydroxy-8-bromonaphthalene , 20.0g, 89.8mmol), tetrakis (triphenylphosphine) palladium (0) (3.5g,3.0mmol), 2M K2CO3 solution (70ml), toluene (200ml), was added after the ethanol (100ml) was refluxed for 12 hours. After completion of the reaction to cool to room temperature and extracted with distilled water and ethyl acetate (EA). The organic layer was dried over anhydrous MgSO4 and remove the solvent by rotary evaporation and dichloromethane and hexane as a developing solvent to give the objective compound was purified by column chromatography to 235-5 (14.5g, 91percent).
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80.0℃; for 12h;Inert atmosphere;
Add <strong>[62456-32-0]1-hydroxy-8-bromonaphthalene</strong> (150.0g, 672.4mmol) to a 2000mL reaction flask,2-nitrophenylboronic acid (123.5 g, 739.7 mmol), tetrakis (triphenylphosphine) palladium (5mol%),Potassium carbonate (278.8g, 2017.3mmol), tetrahydrofuran (8000mL) and water (800mL). The reaction system was heated to 80 C and reacted for 12 hours under the protection of nitrogen.After the reaction was completed, the reaction solution was cooled to room temperature, and extracted with o-dichlorobenzene and water.The organic layer was dried over anhydrous magnesium sulfate, concentrated, and the crude product obtained after recrystallization was passed through a silica gel column to obtain intermediate Sub-1 (114.2 g, yield 64%).
51%
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In ethanol; water; toluene; for 12h;Reflux;
The compound is added 2-nitrophenyl boronic acid (10g, 59.9mmol), 1-hydroxy-8-bromonaphthyl (20.0g, 89 . 8mmol), Pd (PPh3)2Cl2(2.1g, 3 . 0mmol), 2MK2CO3aqueous solution (70 ml), toluene (200 ml) and ethanol (100 ml), and then reflux 12 hours. After the completion of reaction, the resulting reaction product is cooled to the room temperature, distilled water and is then used to extract the EA. Organic layer using an anhydrous MgSO4drying, and the post for rotary evaporimeter to remove the solvent, the use of methylene chloride and hexane as a solvent through the column chromatography purification of the resulting reaction product, to obtain a target compound 30-5 (8.1g, 51%).
With potassium carbonate In acetonitrile at 25℃; for 3h; Inert atmosphere;
236.C Step C. 1 -bromo-8-methoxy -naphthalene.
To a mixture of 8-bromonaphthalen-l-ol (2.90 g, 1.0 eq) in CH3CN (30 mL) were added K2CO3 (5.39 g, 3.0 eq) and Mel (18.5 g, 10.0 eq) in one portion at 25 °C under N2. The mixture was stirred at 25 °C for 3 hours. The reaction mixture was diluted with H2O (30 mL) and extracted with ethyl acetate (3 x 30 mL). The combined organic layers were washed with brine (80 mL), dried over Na2SC>4, filtered and concentrated under reduced pressure to give a residue. The residue was purified by reversed phase flash chromatography [C18, 0. 1% FA in water, 0-78% MeCN] to give l-bromo-8-m ethoxy-naphthalene (2.86 g, 93 %). White solid; NMR (400 MHz, CDCb-d) d = 7.80-7.72 (m, 2H), 7.48-7.38 (m, 2H), 7.26-7.21 (m, 1H), 6.94 (dd, J= 1.6, 7.2 Hz, 1H), 3.98 (s, 3H).
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