Share a compound : 1504-06-9

Electric Literature of 1504-06-9,Some common heterocyclic compound, 1504-06-9, name is 3-Methyloxindole, molecular formula is C9H9NO, 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.

Electric Literature of 1504-06-9,Some common heterocyclic compound, 1504-06-9, name is 3-Methyloxindole, molecular formula is C9H9NO, 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: Preparation of 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, p-Toluenesulfonyl chloride (883 mg, 4.63 mmol) was added, and the resulting mixture stirred for one hour to form pyrimidin-5-ylmethyl 4-methylbenzenesulfonate. In a separate flask 3- methyloxindole (682 mg, 4.63 mmol) and JV,iV-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, 10.2 mmol). The mixture was allowed to warm to 0 0C and stirred for 15 minutes. The mixture was recooled to -78 C. To this mixture was added the tetrahydrofuran solution of pyrimidin-5-ylmethyl 4-methylbenzenesulfonate via cannula; the resulting reaction mixture was allowed to warm to room temperature and was stirred for 18 hours. Water (50 mL) was added, and the mixture extracted with ethyl acetate (2 x 50 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel Biotage 25S, eluting with 0-100% ethyl acetate/hexane to afford 3-methyl-3-(pyrimidin-5-ylmethyl)-l,3-dihydro-2H- indol-2-one as a white solid.1H NMR (CDCl3): delta 8.97 (s, 1 H), 8.29 (s, 2 H), 7.88 (br s, 1 H), 7.25 (d, 1 H, J = 7.3 Hz), 7.20 (m, 1 H), 7.1 1 (m, 1 H), 6.74 (d, 1 H, J = 7.8 Hz), 3.20 (d, 1 H, J – 13.5 Hz), 3.0 (d, 1 H, J – 13.5 Hz), 1.57 (s, 3H) MS: m/e 240.19 (M + H)+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Methyloxindole, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; WO2009/45386; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem