The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 290307-40-3, name is 2-(5-Bromopyridin-2-yl)propan-2-ol. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 290307-40-3
In a 2 L round-bottomed flask was mixed 2,5-dibromopyridine (54 g, 228 mmol) in toluene (600 ml) to give a colorless solution. The reaction was cooled to -78 C. and n-Butyllithium 2.5M hexanes (100 ml, 251 mmol) was added at a rate that the temperature did not exceed -70 C. The reaction was stirred for 30 minutes and then acetone (20.08 ml, 274 mmol) was added quickly. The reaction was stirred for 30 minutes and then quenched with saturated ammonium chloride. The organic layer was washed with brine, dried over sodium sulfate and solvent removed under reduced pressure. The crude residue was purified by column chromatography 20-50% ethyl acetate/heptane to give 42.5 g of 2-(5-bromopyridin-2-yl)propan-2-ol in 86% yield.In a 1 L round-bottomed flask was mixed compound 2-(5-bromopyridin-2-yl)propan-2-ol (10 g, 46.3 mmol) and 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (11.87 g, 50.9 mmol) in dioxane (300 ml). To this was added saturated sodium bicarbonate (150 mL). The reaction mixture was degassed via purging with a stream of nitrogen and then Pd(PPh3)4 (2.67 g, 2.314 mmol) was added. The mixture was heated to reflux becoming very thick then finally going into solution. The reaction was heated for 2 hours, cooled to room temperature and the solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic layer was dried over sodium sulfate and solvent removed under reduced pressure to give 2-(5-(5-amino-2-methylphenyl)pyridin-2-yl)propan-2-ol.The crude product from above was dissolved in dioxane (30 mL) and cooled to 0 C. Sulfuric acid was added to the solution through an addition funnel with manual stirring necessary at the beginning of addition, finally going to solution. The reaction was allowed to exotherm up to 30 C. and stirred for 30 minutes. Upon completion of the reaction as determined by LC/MS, the reaction was poured onto ice, extracted with ethyl acetate (2×200 mL) and the pH of the aqueous was adjusted to 9-10 by addition of 50% sodium hydroxide solution. The mixture was then extracted with ethyl acetate, the organic was washed with brine and dried over sodium sulfate. After removal of solvent the crude product was isolated by column chromatography eluting 0-100% ethyl acetate/heptane to give 4-methyl-3-(6-(prop-1-en-2-yl)pyridin-3-yl)aniline. Yield 9 g, 86% over 2 steps.4-Methyl-3-(6-(prop-1-en-2-yl)pyridin-3-yl)aniline (9 g, 40.1 mmol) was dissolved in ethanol (100 mL) and 10% palladium on carbon (0.5 g) was added. The mixture was hydrogenated at 30 psi for 2 hours. Filtration and concentration of the product afforded clean 3-(6-isopropylpyridin-3-yl)-4-methylaniline. Yield 8 g, 88%
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Reference:
Patent; LOCUS PHARMACEUTICALS, INC.; US2010/41642; (2010); A1;,
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