These common heterocyclic compound, 13220-46-7, name is 4-Methylindolin-2-one, 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. category: indolines-derivatives
5-(2-Hydroxy-3-morpholin-4-yl-propyl)-3-methyl-4-oxo-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-2-carbaldehyde 53f (30 mg, 0.09 mmol) and 4-methyl-1,3-dihydro-indol-2-one (12 mg, 0.08 mmol) were dissolved in 156mul of ethanol, and added with 4.4mul of piperidine to the solution at room temperature. Upon completion of the addition, the reaction mixture was stirred at 45C for 16 hours. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was naturally cooled down to room temperature, and filtered. The filter cake was washed with anhydrous ethanol (1 ml¡Á2) and dried to obtain the title compound (R,Z)-5-(2-hydroxy-3-morpholinopropyl)-3-methyl-2-((4-methyl-2-oxoindolin-3-ylidene)methyl)-5,6,7,8-tetrahydropyrrolo[3,2-c]azepin-4(1H)-one76(12 mg, yield 30%) as a orange solid. MS m/z (ESI): 465.2(M+1) 1NMR(400 MHz, DMSO-d6) delta13.71(s, 1H, pyrrole-NH),10.92 (s, 1H, indole-NH), 7.57(s, 1H, -CH=C), 7.07?6.77(m, 3H, -ArH) , 4.72(d, 1H, -OH),3.90(m, 1H, -CHOH), 3.78(dd, 1H, seven membered ring outer amide-NCH2), 3.58(t, 4H, morpholin intra 2¡Á-CH2O), 3.40(m, 2H, seven membered ring -NCH2), 3.17(dd, 1H, seven membered ring outer amide-NCH2), 2.94(t, 2H, pyrrole-CH2), 2.59(s, 3H, benzylmethyl), 2.44(m, 4H, morpholin intra 2¡ÁCH2N), 2.39(s, 3H, pyrrole -CH3), 2.29(m, 2H, morpholin outer-NCH2), 2.08(m, 2H, seven membered ring CH2-CH2-CH2).
The synthetic route of 4-Methylindolin-2-one has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Shanghai Hengrui Pharmaceutical Co. Ltd.; EP2157093; (2010); A1;,
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