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Substituted Chloro Quinoxaline Lab Report

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To a solution of substituted chloro quinoxaline compound (2a) (4.5g, 12.9 mmol) weighed into a round bottom flask was charged with PdCl2 (dppf).DCM (6%mol, 0.633g). A toluene: ethanol mixture in 2:1 ratio (40 ml+20 mL) was degassed with nitrogen gas, and then added into the flask. Aqueous 1 molar sodium bicarbonate solution (24 mL, 19.30 mmol) was degassed and added to the mixture. The mixture was stirred at room temprature for 15 minutes under nitrogen. The 3-methyl phenyl boronic acid (2.1 g, 15.48 mmol) or respective boronic acid (2-methoxy phenyl boronic acid/ 3-methoxy phenyl boronic acid/ 2-fluoro boronic acid) was added as the solid. The reaction was refluxed under nitrogen gas for overnight and completion was checked by the TLC (Ethylacetate: hexane; 2:3). The reaction mass was cooled to RT. Then the solvent was completely evaporated under reduced pressure. Obtained a black colored product. It was purified by silica column chromatography (10:90 ethyl acetate: hexane) to get the compound (3a-d) …show more content…

TFA (4 times w/v, 18 mL) was slowly added and stirred for 4-6 hours at room temperature. The reaction was monitored by HPLC-MS and TLC. When the reaction was complete, the solvent was concentrated in vacuo; methanol was added (2×50 mL) and evaporated in vacuo. The product was dissolved in methanol and basified with 7N ammonia in methanol. The solvent was concentrated in vacuo and the product was dissolved in methanol (70mL). micro porous tosic acid (MP-TSOH) (12.93 g, 42.83 mmol) was added and the reaction mixture shaken at room temperature for overnight. The resin was washed with methanol, and cleaved with 2N NH3 in methanol. The solvent was evaporated to get the free based compound

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