Application of 1504-06-9, These common heterocyclic compound, 1504-06-9, name is 3-Methyloxindole, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Step 2: 3-methyl-3-(pyrimidin-5-ylmethyl)-l ,3-dihydro-2H-indol-2-onePyrimidin-5-ylmethanol (510 mg, 4.63 mmol) in tetrahydrofuran (8 mL) at room temperature was treated with sodium hydride (185 mg, 4.63 mmol) and stirred for 5 minutes, sodium salt precipates out of solution. p-Toluenesulfonyl chloride (883 mg, 4.63 mmol) was added and the mixture stirred for one hour, to form pyrimidin-5-ylmethyl 4-methylbenzenesulfonate. In a separate flask 3-methyloxindole (682 mg, 4.63 mmol) and A^V-dimethylethylenediamine (1.538 mL, 10.19 mmol) in tetrahydrofuran (16 mL) were cooled to -78 0C and treated dropwise with n-butyllithium (2.5M in hexanes, 4.08 mL, 10.19 mmol). The mixture was allowed to warm to O0Cand stirred for 15 minutes. The mixture was recooled to -78 0C. To this mixture, the tetrahydrofuran solution of pyrimidin-5-ylmethyl 4-methylbenzenesulfonate was added via cannula and the mixture was allowed to warm to room temperature and stirred for 18 hours. Water (50 mL) was added and the mixture was extracted with ethyl acetate (2 x 50 mL). The combined organic fractions were dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel Biotage 25S,
The synthetic route of 1504-06-9 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; MERCK & CO., INC.; WO2009/45381; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem