Heterocyclic Building Blocks-isoxazole

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.36958-61-9,5-(Bromomethyl)-3-methylisoxazole,as a common compound, the synthetic route is as follows.

General procedure: Amine (0.25 mmol), and bromide (0.25 mmol) were taken up in acetonitrile (0.3 mL) in a conical vial equipped with a stirrer bar. Potassium carbonate (0.5 mmol) was added followed by potassium iodide (10 mol%) if required. The vial was sealed with a screwcap and the reaction was stirred at 40 C until thin layer chromatography (TLC) indicated complete consumption of the starting materials. A precipitate was formed during the reaction which was removed by filtration and the filtrate concentrated under reduced pressure. The residue was purified by flash column chromatography and sent to the Netherlands Cancer Institute (NKI) for biological testing.

36958-61-9, 36958-61-9 5-(Bromomethyl)-3-methylisoxazole 10607354, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Article; Milne, Kirsty; Sun, Jianhui; Zaal, Esther A.; Mowat, Jenna; Celie, Patrick H.N.; Fish, Alexander; Berkers, Celia R.; Forlani, Giuseppe; Loayza-Puch, Fabricio; Jamieson, Craig; Agami, Reuven; Bioorganic and Medicinal Chemistry Letters; vol. 29; 18; (2019); p. 2626 – 2631;,
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3405-77-4, 5-Methylisoxazole-3-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,3405-77-4

(R)-Methyl 3-(5-methyl isoxazole-3-carboxamido)-2,3-dihydro-1H-indene-5-carboxylate (B-25)HATU (4.4 g, 11.7 mmol, 1.5 eq) and DIPEA (3.0 ml, 15.6 mmol, 2 eq) were added to an ice-cooled solution of 5-methylisoxazole-3-carboxylic acid (990 mg, 7.8 mmol, 1 eq) in dichloromethane (80 ml), and stirring was carried out for 30 min. (R)-Methyl 3-amino-2,3-dihydro-1H-indene-5-carboxylate (A-07) (7.8 mmol, 1 eq) was dissolved in dichloromethane (20 ml) and added dropwise to the reaction solution, and stirring was carried out for 16 h at RT.The reaction solution was diluted with dichloromethane (250 ml), washed with sat. sodium hydrogen carbonate solution (50 ml), sat. ammonium chloride solution (50 ml), water (50 ml) and sat. NaCl solution (50 ml), dried over sodium sulfate and concentrated under reduced pressure.After purification by column chromatography (silica gel, 2percent MeOH in dichloro-methane), the desired product was obtained in the form of a yellowish solid. Yield: 68percent (1.6 g, 5.3 mmol).

3405-77-4 5-Methylisoxazole-3-carboxylic acid 76947, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; GRUENENTHAL GmbH; US2012/71461; (2012); A1;,
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3356-89-6, 5-Chloro-3-phenylisoxazole is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a stirred suspension of NaH (60% in mineral oil, 440 mg, 11 mmol, prewashed with hexane) in anhydrous THF (20 mL) was added the appropriate alcohol (15 mmol) at r.t. and the reaction mixture was stirred for 0.5 h. Next, 5-chloro-3-phenylisoxazole (2) (1.0 g, 5.6mmol) was introduced as a solid and the mixture was refluxed for 1 h. After cooling to r.t., the mixture was quenched with H2O (20 mL). For 4a and 4b, the resulting precipitate was collected, washed with H2O and recrystallized from hexane-Et2O mixture. For 3a, the reaction mixture was extracted with CH2Cl2 (3 ¡Á 20 mL). The combined organic layers were dried (Na2SO4) and concentrated in vacuo to give isoxazole 3a. 5-tert-Butoxy-3-phenylisoxazole (4c) was synthesized analogously using commercially available potassium tert-butoxide.

3356-89-6, The synthetic route of 3356-89-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Rostovskii, Nikolai V.; Agafonova, Anastasiya V.; Smetanin, Ilia A.; Novikov, Mikhail S.; Khlebnikov, Alexander F.; Ruvinskaya, Julia O.; Starova, Galina L.; Synthesis; vol. 49; 19; (2017); p. 4478 – 4488;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.110256-15-0,5-Cyclopropylisoxazole-3-carboxylic acid,as a common compound, the synthetic route is as follows.

A suspension of 5-cyclopropylisoxazole-3-carboxylic acid (5.00 g, 32.7 mmol) in DCM (30 mL) was treated sequentially with oxalyl chloride (7.15 mL, 81.6 mmol) and DMF (30 muL, 32.7 mmol). The reaction mixture was stirred for 1.5 h at RT, and then concentrated. The resulting residue was suspended in THF (65.3 mL), cooled to 0 C, and then treated with malononitrile (2.59 g, 39.2 mmol) and DIPEA (14.3 mL, 81.6 mmol). After stirring the reaction mixture for 48 h at 0 C, and 2 h at RT, dimethyl sulfate (9.36 mL, 98.0 mmol) was added. The resulting reaction mixture was stirred at 70 C until LCMS indicated complete consumption of starting materials. The mixture then was cooled to RT, and diluted with water (50 mL). The aqueous mixture was extracted with EtOAc. The combined organic extracts were concentrated. The resulting residue was purified by silica chromatography (0-20% EtOAc in hexanes) to afford the title compound (2.27 g, 32%)., 110256-15-0

The synthetic route of 110256-15-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ARRAY BIOPHARMA INC.; BLAKE, James F.; DAI, Donghua; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI,, Gabrielle R.; METCALF, Andrew T.; MORENO, David A.; PRIGARO, Brett; REN, Li; (330 pag.)WO2019/143991; (2019); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.325744-41-0,5-(Chloromethyl)-3-(4-methoxyphenyl)isoxazole,as a common compound, the synthetic route is as follows.

325744-41-0, General procedure: To a stirred solution of ?a? derivatives in freshly distilled CH2Cl2 under N2 atmosphere, at roomtemperature, thionyl chloride (1.5 eq) was added. The reactions were monitored by TLC and, at thetotal consumption of the starting material, they were quenched with cold water and extracted withCH2Cl2. Next, the crude products were solubilized in DMF followed by addition of sodium azide (1.5eq). The reactions were kept at room temperature until TLC analyses indicated the disappearance ofthe starting material, then, they were quenched with water and extracted with EtOAc. In the last step,the crude azide derivatives were solubilized in THF followed by addition of triphenylphosphine (1.5 eq).The reactions were maintained overnight at room temperature, quenched by addition of aqueousNa2CO3 [5% (m/v)] and extracted with EtOAc. The crude amine derivatives (compound d) were usedfor the synthesis of the isoxazolyl-sulfonamide derivatives 1-20 without any further purification.

The synthetic route of 325744-41-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; da Rosa, Rafael; Zimmermann, Lara Almida; de Moraes, Milene Hoeehr; Schneider, Naira Fernanda Zanchett; Schappo, Alice Duarte; Simoes, Claudia Maria de Oliveira; Steindel, Mario; Schenkel, Eloir Paulo; Bernardes, Lilian Sibelle Campos; Bioorganic and Medicinal Chemistry Letters; vol. 28; 20; (2018); p. 3381 – 3384;,
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Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.10557-85-4,3,5-Dimethyl-4-iodoisoxazole,as a common compound, the synthetic route is as follows.

A mixture of 4-bromophenylboronic acid (1 g, 5 mmol), 3,5-dimethyl-4-iodoisoxazole (0.93 g, 4.2 mmol), bis(triphenylphospine)palladium(II) chloride (59 mg, 2 mol %), NaHCO3 (1.06 g, 12.6 mmol) in DME (5 mL) and H2O (5 mL) was heated to 80 C. under N2 for 18 h. The reaction mixture was partitioned between 1 N HCl and EtOAc. The organic layer was washed with saturated NaHCO3, brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography (5% EtOAc in hexanes) to give the title compound as a white solid (0.9 g, 86%). 1H NMR (CDCl3): delta 2.26 (s, 3H), 2.40 (s, 3H), 7.13 (d, 2H, J=8.3 Hz), 7.58 (d, 2H, J=8.3 Hz)., 10557-85-4

As the paragraph descriping shows that 10557-85-4 is playing an increasingly important role.

Reference£º
Patent; Agouron Pharmaceuticals, Inc.; US2005/176701; (2005); A1;,
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10557-85-4, 3,5-Dimethyl-4-iodoisoxazole is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Under argon protection and liquid nitrogen acetone bath conditions,4-iodo-3,5-dimethylisoxazole (1) (1.12 g, 5 mmol) was dissolved in 50 mL of purified tetrahydrofuran.N-butyllithium (5 mmol, 2.3 mL) was added under rapid stirring,Continue to low temperature reaction for 0.5 hours;Perfluorinated cyclopentene (5 mmol, 0.7 mL) was rapidly injected with high speed stirring,Continue to low temperature reaction after 1.0 hoursThen rose to room temperature, and then add the appropriate amount of water to terminate the reaction.The solvent was removed and extracted with ether. The organic phases were combined,Washed three times with saturated brine and distilled water, and dried overnight without anhydrous MgSO4. The solvent was removed by vacuum rotary evaporation and eluted with petroleum ether as eluant. The product was purified by silica gel column and the product was 3.1 g as an orange liquid. The yield was 71%., 10557-85-4

The synthetic route of 10557-85-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Jiangxi Science and Technology Normal University; Pu Shouzhi; Liu Gang; Ma Lele; Fan Congbin; Cui Shiqiang; (15 pag.)CN104945393; (2017); B;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.14441-90-8,5-Phenylisoxazole-3-carboxylic acid,as a common compound, the synthetic route is as follows.

General procedure: Thionyl chloride (1.2 mL) was added at 0 C to the 3-phenylisoxazole-5-carboxylic acid 13 or the 5-phenylisoxazole-3-carboxylic acid 14 or the 5-(4-chlorophenyl)isoxazole-3-carboxylic acid 15 or the 3-(4-methylphenyl)isoxazole-5-carboxylic acid 16 (0.3 g, 1.58 mmol). The obtained suspension was stirred and heated at reflux for 16 h and then cooled at 0 C. At this temperature, a new addition of thionyl chloride (1.2 mL) was followed by another heating at reflux for 2 h. The reaction mixture was cooled at room temperature and the thionyl chloride excess was evaporated to dryness in vacuo. Anhydrous THF (2 mL) was added to the crude product. To the resulting solution, cooled at -5 C, was added dropwise a solution of appropriate amine (3.16 mmol) in dry THF (2 mL). The reaction mixture was stirred at room temperature for ca. 90 min (TLC, petroleum ether/ethyl acetate) and then the solid mass was filtered off and washed with THF. The filtrate was evaporated to dryness; the residue was treated with saturated sodium bicarbonate solution (20 mL) and extracted with dichloromethane (3¡Á15 mL). The combined organic phases were dried (Na2SO4) and evaporated to dryness to give the crude product, purified by flash-chromatography to give the desired amide.

14441-90-8, As the paragraph descriping shows that 14441-90-8 is playing an increasingly important role.

Reference£º
Article; Cosimelli, Barbara; Simorini, Francesca; Taliani, Sabrina; La Motta, Concettina; Da Settimo, Federico; Severi, Elda; Greco, Giovanni; Novellino, Ettore; Costa, Barbara; Da Pozzo, Eleonora; Bendinelli, Sara; Martini, Claudia; European Journal of Medicinal Chemistry; vol. 46; 9; (2011); p. 4506 – 4520;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.62348-13-4,Isoxazole-5-carbonyl chloride,as a common compound, the synthetic route is as follows.

62348-13-4, General procedure: A solution of the corresponding acyl chloride 1-10 (9.18 mmol) in chloroform (25 mL) was slowly added dropwise to a stirred solution of compounds a-c (4.59 mmol) in dry chloroform (40 mL) and pyridine (5 mL). The mixture was stirred for 48 h at room temperature. Solvents were removed under vacuum by rotatory evaporation and the residue was treated with water (100 mL) and purified.

The synthetic route of 62348-13-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Ibanez, Elena; Plano, Daniel; Font, Maria; Calvo, Alfonso; Prior, Celia; Palop, Juan Antonio; Sanmartin, Carmen; European Journal of Medicinal Chemistry; vol. 46; 1; (2011); p. 265 – 274;,
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288-14-2, Isoxazole is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 12 4-[5-Benzyloxymethyl-3-(4-fluoro-phenyl)-isoxazol-4-yl]-2-methylsulfanyl-pyrimidine (Compound 8). To a stirred solution of the above compound 7 (13.75 g, 47.7 mmol) and Et3N (14.6 mL, 105 mmol) in EtOH (200 mL), was added a solution of 4-fluoro-benzoylchloride oxime (56 mmol) in EtOH (50 mL) over 30 min. The solution was stirred at 25 C. for 15 min. Then, the solution was heated to reflux for 90 min. The solution was cooled to 25 C. Additional Et3N (7.3 mL, 52 mmol) was added followed by dropwise addition of a solution of 4-fluoro-benzoylchloride oxime (38.5 mmol) in EtOH (50 mL) over 1 h. to drive the reaction to completion. The solution was refluxed for 1 h. until TLC indicated that all of the starting isoxazole was consumed. The solution was cooled to 25 C. and concentrated. The crude material was picked up in CH2Cl2 (50 mL) and poured into saturated aqueous NaHCO3 (150 mL), extracted with CH2Cl2 (3*150 mL), dried (MgSO4), filtered and concentrated. Flash chromatography (SiO2, 20% EtOAc-hexanes) provided the title compound (14.2 g, 34.8 mmol, 60%) in sufficient purity (>85%) for use in the next reaction.

288-14-2, The synthetic route of 288-14-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Green, Jeremy; Bemis, Guy; Grillot, Anne-Laure; Ledeboer, Mark; Salituro, Francesco G.; Harrington, Edmund; Gao, Huai; Baker, Christopher; Cao, Jingrong; Hale, Michael; US2003/149051; (2003); A1;,
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