Category: Isoxazoles

954230-39-8, Ethyl 3-(4-fluorophenyl)-5-methylisoxazole-4-carboxylate is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,954230-39-8

o a solution of 3-(4-fluoro-phenyl)-5-methyl-isoxazole-4-carboxylic acid ethyl ester (3.0 g, 12 mmol) (6.18 g, 25 mmol) in THF (320 mL) was added portionwise lithiumaluminiumhydride (528 mg, 14 mmol) at 0 C and the reaction mixture was stirred at room temperature for 3 h. The mixture was then cooled to 0 C and water (518 mu) added followed by sodium hydroxide (15% solution, 518 mu) and then again water (1.5 mL) and the mixture then stirred overnight at room temperature. The precipitate was then filtered off and washed with THF. The combined washings and filtrate were then evaporated. Purification by chromatography (Si02, heptane:ethyl acetate = 100:0 to 1: 1) afforded the title compound (1.8 g, 71%) which was obtained as a white solid. MS: m/e = 208.1 [M+H]+.

The synthetic route of 954230-39-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; DOTT, Pascal; GRASSMANN, Olaf; KAMMERER, Michael; MANNS, Joachim; SCHWITTER, Urs; THOMAS, Andrew; WYTTENBACH, Nicole; WO2013/57124; (2013); A1;,
Isoxazole – Wikipedia
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.954230-39-8,Ethyl 3-(4-fluorophenyl)-5-methylisoxazole-4-carboxylate,as a common compound, the synthetic route is as follows.,954230-39-8

Step d) r3-(4-Fluorophenyl)-5-methyl-isoxazol-4-yll -methanol Alternative 2) Preparation by reduction of the ethyl ester (i) with L1AIH4 as reducing agent: To a suspension of LiAlH4 (75.9 mg, 2.0 mmol) in THF (2 mL) was added at 0-10C within 15 minutes a solution of 3-(4-Fluoro-phenyl)-5-methyl-isoxazole-4-carboxylic acid ethyl ester (0.50 g, 2.0 mmol) in THF (3 mL) and the resulting solution was allowed to warm to room temperature and subsequently stirred at this temperature for at least one hour. Water (15 mL) was added dropwise and the resulting suspension was then filtered and the filter cake washed with ethyl acetate (15 mL). From the biphasic filtrate the layers were separated and the organic layer was washed with water (1×15 mL). Both combined aqueous layers were back extracted with ethyl acetate (2×15 mL). The combined organic layers were dried over Na2S04 and subsequently concentrated to dryness (45C/25 mbar) to afford 0.375 g (90%) of the title compound as a slightly yellow solid with a purity of 100% (by HPLC).

The synthetic route of 954230-39-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; DOTT, Pascal; HANLON, Steven Paul; HILDBRAND, Stefan; IDING, Hans; THOMAS, Andrew; WALDMEIER, Pius; WO2013/57123; (2013); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

89102-73-8, Isoxazol-3-ylmethanol is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,89102-73-8

(b) 3-Chloromethyl isoxazole A solution of 3-hydroxymethyl isoxazole (4.23 g, 43 mmol) and triphenylphosphine (11.3 g, 42 mmol) in carbon tetrachloride (100 ml) was heated at reflux for 18 h. Solvent was removed under reduced pressure then the residue taken up in ether and filtered. The filtrate was concentrated under reduced pressure and further purified by short path distillation (bp 60 C. at 10 mm) to give the desired chloride (1.41 g, 12 mmol, 28%); deltaH (CDCl3) 4.50 (2H, s, CH2 –Cl), 6.40 (1H, d, J 2 Hz, CH-4), 8.40 (1H, d, J 2 Hz, CH-5).

The synthetic route of 89102-73-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Beecham Group p.l.c.; US4812470; (1989); A;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.87988-94-1,5-Methylisoxazol-4-amine,as a common compound, the synthetic route is as follows.,87988-94-1

EXAMPLE 2 4-Difluoromethoxy-2-ethylbenzooxazole-7-carboxylic acid (3-methylisoxazole-4-yl)-amide Starting from 4-difluoromethoxy-2-ethylbenzooxazole-7-carboxylic acid (150 mg) and 5-methylisoxazol-4-ylamine (60 mg). Purification by column chromatography on silica eluding with 50% ethyl acetate in heptane afforded the title compound as a white solid (110 mg). TLC Rf 0.32 (ethyl acetate). M.p. 103-104.5 C.

The synthetic route of 87988-94-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Darwin Discovery, Ltd.; US6403791; (2002); B1;,
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59669-59-9, 3-(tert-Butyl)isoxazol-5-amine is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,59669-59-9

Step 7: Synthesis of compound D-8Activation of 60 g (0.25 mol) of compound D-7as the corresponding acid chloride is achieved by treatment with thionyl chloride (0.9 L, 12.39 mol) at 60 ¡ãC for 1.5 h. The reaction is cooled to room temperature and acid chloride mixture was evaporated to dryness. The acid chloride mixture is dissolved in DCM (200 mL).This acid chloride solution is added dropwise over 20 mins to a stirred suspension of 36 g (0.25 mol) of 3-tert-butyl-isoxazol-5-ylamine and 0.6 L (0.50 mol) of N,N- diisopropylethylamine in DCM (400 mL) at 35 ¡ãC. After complete addition the reaction is stirred at room temprature for 17 h. The solvent is removed under reduced pressure. The residue is purified by dry-flash column chromatography (silica, eluent heptanes, 20percent ethyl acetate) to yield 50 g of light brown solid. Solid is re-crystallized from (50percent IPA in heptane) to afford 34 g of compound D-8 Yield: 43percent; ES-MS: m/z 359 [M+H];’H-NMR (400 MHz, CHLOROFORM-d) delta ppm 1.33 (9 H, s), 1.76 (6 H, s), 1.83 – 1.91 (2H, m), 1.92 – 2.05 (2 H, m), 3.34 – 3.51 (3 H, m), 4.07 (2 H, ddd, 7=11.86, 2.20, 2.08 Hz), 6.27 (1 H, s), 9.60 (1 H, s)

The synthetic route of 59669-59-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HICKEY, Eugene Richard; RIETHER, Doris; ERMANN, Monika; WO2012/12307; (2012); A1;,
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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.3209-70-9,Ethyl isoxazole-3-carboxylate,as a common compound, the synthetic route is as follows.,3209-70-9

(i) The preparation of 3-aminomethylisoxazole is described below: Di-isobutylaluminium hydride (1.5M in toluene, 29 ml) was added to a solution of ethyl isoxazole-3-carboxylate (6.1 g; Can. J. Chem., 1970, 48, 475) in toluene (20 ml) which was cooled in an ice-bath. The mixture was stirred at laboratory temperature for 16 hours. The analysis indicated that the reduction was incomplete. A second portion of di-isobutylaluminium hydride (28.8 ml) was added and the mixture was stirred for 16 hours. The bulk of the toluene was evaporated and the mixture was poured into a saturated aqueous ammonium chloride solution. The precipitate was filtered off and dried. There was thus obtained 3-hydroxymethylisoxazole (2.1 g).

The synthetic route of 3209-70-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Imperial Chemical Industries PLC; National Research Development Corporation; US5089499; (1992); A;,
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28883-91-2, 5-Amino-3-(4-methylphenyl)isoxazole is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,28883-91-2

General procedure: A 0.1 M NaClO4solution (50 ml) in MeCN containing NH4SCN (6 mmol, 0.46 g) and indole (1a)(2 mmol, 0.24 g) was placed in a glass cell with coaxally positioned Ptelectrodes (San. = 26 cm2, Scat. = 10 cm2). The electrolysis was performed atE = 0.70 V vs SCE (CPE) or at j = 2.5 mA/cm2 (GE). After passing of 2.1 F ofelectricity in CPE (or 2.5 F in GE) calculated on the basis of 1 F/NH4SCN mol, theelectrolysis was terminated and the MeCN was distilled off. H2O (10 ml) wasadded and the residue was extracted with CH2Cl2 (4 25 ml). The extractswere combined, dried over anhydrous Na2SO4, filtered and the solvent wasdistilled off. The residue was purified by column chromatography on silica gel(eluent-a mix of light petroleum and EtOAc with a buildup of the volumefraction of the latter from 5% to 20%) to afford pure 3-thiocyanato-1H-indole

The synthetic route of 28883-91-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Kokorekin, Vladimir A.; Sigacheva, Vera L.; Petrosyan, Vladimir A.; Tetrahedron Letters; vol. 55; 31; (2014); p. 4306 – 4309;,
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2510-36-3, 3,5-Dimethylisoxasole-4-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,2510-36-3

General procedure: A solution of the deprotected azaspiro compound (0.134 mmol) in 2 mL of DMF, 0.14 mL of DIPEA (0.803 mmol), 51.8 mg of EDC (0.268 mmol) and 27.9 mg of HOBT (0.201 mmol) was stirred for 15 min at r.t. Then the proper acid (0.125 mmol) was added to the mixture and the reaction was maintained at 50 C for 12 h with stirring.

The synthetic route of 2510-36-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Francesconi, Valeria; Giovannini, Luca; Santucci, Matteo; Cichero, Elena; Costi, Maria Paola; Naesens, Lieve; Giordanetto, Fabrizio; Tonelli, Michele; European Journal of Medicinal Chemistry; vol. 155; (2018); p. 229 – 243;,
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Isoxazole | C3H3NO – PubChem

21169-71-1, Isoxazole-5-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,21169-71-1

General procedure: Compounds were synthesized in solution phase using Boc-protected amino acids on 100-200mg scale. Firstly, the amino acid (1.2-1.5equiv) was activated with HBTU (1.5equiv) and DIPEA (1.5equiv) as 0.2-0.5M solution in DMF for 10min. Then the solution was added to an amino group bearing C-terminal moiety (R1R2NH) and the mixture was stirred for a minimum of 1h at room temperature. The reaction mixture was diluted with EtOAc and washed with saturated NaHCO3 (2¡Á). The organic extracts were dried over MgSO4, filtered and evaporated in vacuo. The crude product was then treated with 20% TFA in DCM and stirred for 1-2h to remove the Boc group. TFA was removed by evaporating the reaction mixture under a stream of N2. The residue was dissolved in DCM and washed with saturated NaHCO3 (2¡Á). DCM phase was dried with MgSO4, filtered and evaporated in vacuo. Subsequent N-Boc-amino acids and amines were sequentially coupled under the same conditions. Each coupling reaction was monitored by ESMS, with most reactions going to completion overnight. All final compounds were purified on rpHPLC (97% by analytical HPLC) and fully characterized by NMR and HRMS (yields between 30% and 40%).

The synthetic route of 21169-71-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Yau, Mei-Kwan; Liu, Ligong; Lim, Junxian; Lohman, Rink-Jan; Cotterell, Adam J.; Suen, Jacky Y.; Vesey, David A.; Reid, Robert C.; Fairlie, David P.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 3; (2016); p. 986 – 991;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

21169-71-1, Isoxazole-5-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,21169-71-1

Procedure S: Ethyl 2-(isoxazol-5-yl)-2-oxoacetate; To a solution of 4.7 g (40.7 mmol, 1.0 eq.) of isoxazole-5-carboxylic acid in 70 mL of anhydrous THF at -78 C under an argon atmosphere was added 4.5 mL (40.7 mmol, 1.0 eq.) of iV-methylmorpholine followed by 5.3 mL (43 mmol, 1.05 eq.) of isobutyl chloroformate. The mixture stirred at -78 C for 20 min. The mixture was filtered and the filtrate was allowed to warm to 0 C and excess diazomethane added slowly. The mixture was allowed to warm to room temperature and stirred for 16 h. A solution of 25 mL of 33% HBr in acetic acid was added and the mixture stirred at room temperature for 10 min. The mixture was diluted with 400 mL of EtOAc and washed with 10% citric acid followed by sat. NaHCO3 and sat. brine. The organic phase was dried (Na2SO4) and the solvent removed in vacuo. The residue was purified by flash chromatography to provide 5.2 g of 2-bromo-l-(isoxazol-5- yl)ethanone as a white solid. The 2-bromo-l-(isoxazol-5-yl)ethanone was redissolved in 300 mL of ethanol and 3.3 g (30 mmol) of selenium dioxide added. The mixture heated at 100 C for 16 h. The mixture was allowed to cool to room temperature and filtered. The solvent was removed in vacuo and the residue partitioned between EtOAc and sat. NaHCO3. The layers were separated and the aqueous phase extracted with EtOAc. The combined organic extracts were washed with sat. brine, dried (Na2SO4) and the solvent removed in vacuo. The residue was purified by flash chromatography to provide 1.8 g of ethyl 2-(isoxazol-5-yl)-2- oxoacetate. deltaH (300 MHz, CDCl3) 1.43 (t, 3H), 4.47 (q, 2H), 7.40 (d, IH), 8.45 (d, IH).

The synthetic route of 21169-71-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; LIGAND PHARMACEUTICALS INC.; COLE, Andrew; MCGUINNESS, Brian, F.; SHAO, Yuefei; DONG, Guizhen; HENDERSON, Ian; WO2010/8775; (2010); A1;,
Isoxazole – Wikipedia
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