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With palladium diacetate; triphenylphosphine; potassium hydroxide; In acetonitrile; for 24h;Inert atmosphere; Reflux;
General procedure: 2,4-dibromopyridine (0.12 g, 0.50 mmol), phenylboronic acid pinacol ester (0.11 g, 0.55 mmol), KOH (56 mg, 1.0 mmol), Pd(OAc)2 (11 mg, 5 mol %), PPh3 (52 mg, 20 mol %) were dissolved in CH3CN (6 mL). The reaction was stirred at 70 C under nitrogen atmosphere for 24 h and then cooled. The solid was filtrated off and the filtrate was concentrated. The crude product was then dissolved in CH2Cl2 (10 mL) and the solution was washed with water (10 mL*3) and brine (10 mL), and dried over sodium sulfate. Upon evaporation, the resulting residue was subjected to column chromatography (petroleum ether/AcOEt, 400:1) to give 3w (104 mg, 89%) as a colorless liquid.
With palladium(II) trifluoroacetate; triphenylphosphine; potassium hydroxide; In acetonitrile; at 30℃; for 24h;Inert atmosphere;
General procedure: 2,5-dibromopyridine (0.12 g, 0.50 mmol), phenylboronic acid (67 mg, 0.55 mmol), K2CO3 (0.14 g, 1.0 mmol), Pd(OAc)2 (11 mg, 5 mol %), PPh3 (26 mg, 10 mol %) were dissolved in CH3CN/CH3OH (2:1, 6 mL). The solution was stirred at 50 C under nitrogen atmosphere for 24 h and then cooled and the solid was filtered off. The filtrate was then concentrated and the resulting crude product was dissolved in CH2Cl2 (10 mL). The solution was washed with water (10 mL*3) and brine (10 mL), and dried over sodium sulfate. Upon removal of the solvent with a rotavapor, the resulting residue was subjected to column chromatography (petroleum ether/AcOEt, 400:1) to give the desired product 3a (114 mg, 97%) as a white solid.
4-chloro-6-phenyl-8-thia-3,5-diazatricyclo[7.4.0.0,]trideca-1(13),2,4,6,9,11-hexaene[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
44%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 90℃;
The starting material, 2,4-dichlorobenzo [4,5] thieno [3,2-d] pyrimidine (70.84 g,277.7 mmol) dissolved in THF in a round bottom flask after, Sub 2-136 (62.33 g, 305.4mmol) , Pd (PPh3) 4 (12.83 g, 11.1 mmol), K2CO3 (115.13 g, 833 mmol), water wasadded and the resulting mixture was stirred at 90 C. After the reaction was completedCH2Cl2 and water, drying over MgSO4 the organic layer was extracted andrecrystallized silicagel column and the resulting compound and then concentrated to give36.26 g product: was obtained (yield: 44%).2.Sub 1A-9 Synthesis& Lt; Reaction Formula 6 & gt;[Image]
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; bis(pinacol)diborane; In 1,4-dioxane; water; at 20 - 90℃;
General procedure: (1) General preparation method of L1 compound:2nl water and 10ml 1,4-dioxane were sequentially added to a 100ml round bottom flask.Stir well and mix, then add 2-amino-5-bromo-1,2,4-triazole [1,5-a]pyridine (2 mmol), pinacol ester (2.5 mmol), K2CO3 (5 mmol) , PdCl2dppf (0.1 mmol), stirring at room temperature for 10 minutes,Transfer the reaction flask to an oil bath at 90 C and reflux.Continue to react for 3-5 hours,TLC detected until the end of the reaction (developing agent: 5% CH3OH / CH2Cl2);The reaction was then stopped by adding 10 ml of water to the flask, and extracted with CH 2 Cl 2 (3×50 ml).The organic phases were combined, 5 g of anhydrous magnesium sulfate was added, and filtered.Concentrated, dried and separated on silica gel column to obtain intermediate L1(silica gel 15 g, elution: CH3OH/CH2Cl2).
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; for 36h;Reflux; Inert atmosphere;
General procedure: First, the product E2-2 is obtained from E2-1 through the Suzuki cross coupling reaction according to the above route, and then the product E2-2 is sequentially processed according to the above reaction scheme to obtain the product E2-4. E2-4 (6.46g, 17.60mmol), E1-1 (2.64g, 8.00mmol) were added to a 500mL round-bottomed flask, and a mixed system of toluene (150ml), ethanol (50mL) and deionized water (100mL) was used as Solvent, add Na2CO3 (6.12g, 57.78mmol) and Pd(PPh3)4 (1.08g, 0.933mmol) as catalyst, heat under reflux for 36 hours, filter after cooling, and successively use ethanol, dichloromethane/methanol mixed solution for many times The filter cake was washed and further processed by conventional methods to give the final product E-2 (3.22 g, 54% yield).
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