* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With potassium carbonate; sodium sulfate;copper; In nitrobenzene; at 220℃; for 7h;Inert atmosphere;
The following reagents and solvent were loaded into a reactor.10H-Phenoxazine: 10.0 g (54.58 mmol)Methyl 2-bromo-4-chlorobenzoate : 15.12 g (60.65 mmol) Copper: 3.85 g (60.65 mmol)Potassium carbonate: 8.38 g (60.65 mmol)Sodium sulfate: 8.61 g (60.65 mmol)Nitrobenzene: 125 ml [0110] Next, the reaction solution was stirred with heating under nitrogen at 220°C for 7 hours. After the completion of the reaction, the reaction solution was concentrated under reduced pressure. To the resultant residue was added ethyl acetate, and the mixture was then washed with an aqueous solution of ammonium chloride. The organic layer was concentrated under reduced pressure to give a crude product. Next, the resultant crude product was purified by columnchromatography (silica gel) to afford 15.9 g of methyl 5-chloro-2- ( lOH-phenoxazin-10-yl ) benzoate (yield: 83percent)
Except that 3-aminopyridine-2-thiol was used instead of 2-amino-4-hydroxypyridine, and 5-bromoisophthalate replaced by 2,2'-dibromo-4,4'-dicarboxy biphenyl, other synthesis process with Example 22. Purified by silica gel column chromatography to give a solid Compound 12 (9.0g, 21percent yield).
With potassium phosphate; In N,N-dimethyl-formamide; for 16h;Reflux;
lOg (54.6 mmol) Phenoxazine, 14.2 g (82 mmol) 1,3-dichloro-2-fluoro- benzene and 25 g (0.11 mol) potassium phosphate were dissolved in 250 mL DMF and stirred 16 hours at reflux. After cooling down to roomtemperature 300 ml toluene and 500 ml water was added and the phaseswere separated. The organic phase was washed with water (3x300 ml) and the aqueous phase was extracted two times with toluene. The combined organic phases were reduced to dryness and purified by recrystallizationfrom toluene/heptane.Yield: 16 g (0.05 mol; 90 %)
With tri-tert-butyl phosphine; palladium diacetate; caesium carbonate; In toluene; for 10h;Inert atmosphere; Reflux;
Synthesis of Compound 57: The compound 57a (3.9 g, 15.0 mmol),Phenoxazine (2.9 g, 16 mmol),Tert-butylphosphine (0.35 g, 2 mmol),Palladium acetate (0.4 g, 1.8 mmol) and cesium carbonate (9.7 g, 30 mmol) were dissolved in toluene,Under a nitrogen atmosphere,The reaction was heated under reflux for 10 hours.The solvent was evaporated in vacuo,The remaining material was stirred with pentane,filter,Purification by silica gel column chromatography,To obtain solid compound 5, (3.7 g, 10.2 mmol),Yield 62percent.
With copper; potassium carbonate; In 1-methyl-pyrrolidin-2-one; for 48h;Inert atmosphere; Reflux;
Under nitrogen protection,Intermediate a obtained in Intermediate Preparation Example (3.61 g, 9 mmol)And phenoxazine (4.12 g, 22.5 mmol)Dissolved in 50 mL of NMP (N-methylpyrrolidone)Then catalyst copper (1.72 g, 27 mmol)Acid-binding agent and potassium carbonate (4.97g, 36mmol).The system was warmed to reflux for 48 hours,Natural cooling to 20 ~ 25 after adding 100mL water quenching reaction,The product was filtered to give the crude product.The crude product was purified by silica gel column chromatography,The eluent was dichloromethane: n-hexane = 1: 7 (V / V),A white powder is obtained. The resulting powder is further sublimated and purified by a chemical vapor deposition system at a sublimation temperature of 225 ° C to obtain the compound C01 in a yield of 63percent.
6.37 g (35 mmol) of phenoxazine was added to a 250 ml three-necked flask, and 100 ml of N,N-dimethylformamide was added as a reaction solvent, and the mixture was stirred on a magnetic stirrer for 10 min under ice bath. 0.72 g (30 mmol) of NaH was added portionwise to the reaction flask and stirring was continued for 1 h.Dissolve 2.07 g (10 mmol) of <strong>[3029-64-9]2,4,6-trichloro-5-cyanopyrimidine</strong> in 40 mlThe N,N-dimethylformamide solution was added dropwise to the reaction system, and after the addition was completed, the reaction was carried out at room temperature for 24 hours. After the reaction was completed, the reaction solution was poured into 200 ml of 10percent diluted hydrochloric acid, and the mixture was filtered under reduced pressure, washed with water and dried, and the crude product was obtained from petroleum ether and dichloromethane (PE: DCM=10: 1) Pass the column for the mobile phase. 3.91 g of a white solid powder was obtained in a yield of 60.3percent.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
120K+ Compounds
Competitive Price
1-2 Day Shipping
