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Into a 500 ml three-necked flask, 100 mL of acetic acid was added, and Compound 2 (20 g, 0.11 mol) was added dropwise to a 100 mL aqueous solution of 40% hydrogen bromide at 0C. The reaction was completed after 30 minutes of dropwise addition. A 50 ml aqueous solution of sodium nitrite (20.7 g, 0.33 mol) was added dropwise at a controlled temperature of 0C. After 30 minutes of reaction, the reaction is complete and it is quenched by the dropwise addition of 30 ml of 10% sodium bisulfite solution. Ethyl acetate extraction (200ml×2), dried over 20g of anhydrous sodium sulfate, The mixture was concentrated by suction filtration to obtain a white solid compound 3 (23.3 g, yield 87%).
With lithium hydroxide monohydrate; In tetrahydrofuran; water; at 0℃; for 1h;
To a 250 ml three-neck flask was added 50 ml of tetrahydrofuran, 50 ml of water, and Compound 3 (20 g, 0.08 mol). Lithium hydroxide monohydrate (5 g, 0.12 mol) in water/70 ml of water was added dropwise. The reaction was completed at 0C for 1 hour. The reaction is complete. Methyl tert-butyl ether extraction (30 ml x 2). The aqueous phase was adjusted to pH=1 with 4N hydrochloric acid and extracted with dichloromethane (50 ml×3). Dry 10 g of anhydrous sodium sulfate and spin-dry to obtain white solid compound 4 (18 g, yield 96%).
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 100℃;Inert atmosphere;
Take compound IV (1.3g, 5mmol), 2,3-dichlorophenylboronic acid (1.1g, 6mmol), K2CO3 (1.4g, 10mmol), Pd[P(C6H5)3]4 (0.3g, 0.25mmol) In a mixed solution of dioxane (18 mL)/water (2 mL), heat and stir at 100 C. under the protection of nitrogen until TLC indicates that the reaction is complete.After the reaction mixture was cooled to room temperature, it was poured into ice water (20 mL), stirred, and extracted with dichloromethane (20 mL×3). The extracted organic phases were combined, washed with water (50 mL×3), and dried over anhydrous sodium sulfate. The dried organic phase was evaporated on a rotary evaporator to remove the solvent, and the obtained residue was purified by column chromatography to obtain product X-1, 1.1 g, with a yield of 70%.
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