With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.19788-37-5,4-(Chloromethyl)-3,5-dimethylisoxazole,as a common compound, the synthetic route is as follows.
General procedure: Intermediate 22: N-{1-[(6-methyl-2-pyridinyl)methyl]-1H-pyrazol-3-yl}acetamide Intermediate 1 (97 mg, 0.774 mmol) was dissolved in 8 mL of THF (anh), at 0 C. NaH (ALDRICH, 31 mg, 0.774 mmol) was added, and mixture of reaction was stirred at 0 C. for 30 minutes. A solution of Intermediate 11 (144 mg, 0.774 mmol) in 2 mL THF (anh) was added to the mixture. Reaction was heated at 75 C. overnight. Mixture of reaction was partitioned between distilled water, EtOAc (*3) and DCM. Organic layers were dried over MgSO4 (anh) and filtered. Solvent was evaporated under vacuum. Residue was purified by silica chromatography column using a linear gradient of DCM/MeOH as eluents to give the title compound (133 mg, 0.578 mmol, 75% yield). 1H NMR (300 MHz, DMSO-d6) delta ppm: 10.40 (br s, 1H), 7.72 (d, 1H), 7.60-7.66 (m, 1H), 7.17-7.16 (m, 1H), 6.74-6.77 (m, 1H), 6.49 (d, 1H), 5.24 (s, 2H), 2.44 (s, 3H), 1.95 (s, 3H). [ES+MS] m/z 231 (MH+). The Intermediates 23-39 were prepared by methods analoguous to that described for Intermediate 22 but replacing the benzyl halide (Intermediate 11) with that indicated in Table 3. Modifications are also indicated. Reaction times varied from 2 h to 3 h.
As the paragraph descriping shows that 19788-37-5 is playing an increasingly important role.
Reference£º
Patent; GLAXO GROUP LIMITED; Castro Pichel, Julia; Fernandez Menendez, Raquel; Fernandez Velando, Esther Pilar; Gonzalez Del Valle, Silvia; Mallo-Rubio, Araceli; US2013/203802; (2013); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem