Preparation method of 3-(2-chloro-pyrimidine-4-yl)-1-methylindole
A technology of methyl indole and chloropyrimidine, which is applied in the field of medicine, can solve the problems of high pollution after treatment and dangerous reaction, and achieve the effect of high yield, safety and easy cost
Inactive Publication Date: 2017-05-17
山东轩德医药科技有限公司
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[0005] In the current prior art, such as WO2013 / 14448 A1, 2013, CN105237515 A, 2016, the preparation method of Osimertinib Mesylate and its intermediates is introduced, but the preparation method needs to use highly toxic substances such as methyl iodide, and the reaction is dangerous and Post-processing pollution is large
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Embodiment 1
[0022] Example 1: Preparation of 3-(2-chloropyrimidin-4-yl)-1-methylindole
[0023]
[0024] With 1.5L methanol, 3-(2-chloropyrimidin-4-yl)-1H-indole (229g), formaldehyde (90g), 10% palladium carbon (20g) was added in the reaction kettle, under hydrogen atmosphere (0.2MPa) , stirred at room temperature for 3 hours, the reaction was completed, filtered, the organic phase was evaporated to dryness, and recrystallized with acetonitrile to obtain the product 3-(2-chloropyrimidin-4-yl)-1-methylindole, 210g, yield: 86.4 %.
[0025] 1H NMR (400MHz, 25℃, DMSO-d6): 3.90(3H,s), 7.30(2H,pd), 7.54-7.60(1H,m), 7.82(1H,d), 8.38-8.44(1H,m ), 8.49(1H,s), 8.53(1H,d).
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The invention relates to a preparation method of 3-(2-chloro-pyrimidine-4-yl)-1-methylindole. According to the method, formaldehyde is adopted as a reaction material, the reaction technology is simple and convenient, the security is high, the yield is high and the mass production can be carried out.
Description
[0001] 1. Technical field [0002] The invention belongs to the technical field of medicine and relates to a method for preparing 3-(2-chloropyrimidin-4-yl)-1-methylindole. [0003] 2. Background technology [0004] Osimertinib (Osimertinib Mesylate, Tagrisso) is a targeted anticancer drug developed by AstraZeneca. It was approved for marketing by the European Medicines Agency (EMA), and then approved for marketing by the Japanese Pharmaceuticals and Medical Devices Administration (PMDA) on March 28, 2016. This drug is used to treat EGFR-T790 mutation-positive non-small cell lung cancer. 3-(2-Chloropyrimidin-4-yl)-1-methylindole is a key intermediate in the synthesis of Osimertinib Mesylate. [0005] In the current prior art, such as WO2013 / 14448 A1, 2013, CN105237515 A, 2016, the preparation method of Osimertinib Mesylate and its intermediates is introduced, but the preparation method needs to use highly toxic substances such as methyl iodide, and the reaction is dangerous a...
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IPC IPC(8): C07D403/04
CPCC07D403/04
Inventor 董岩岩
Owner 山东轩德医药科技有限公司