2058-74-4, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 2058-74-4 as follows.
A solution of N-methylisatin (322 mg, 2.0 mmol), indole (258 mg, 2.2 mmol), and K 2 CO 3 (138 mg, 1.0 mmol) in aqueous DMF (H 2 O/DMF, 2:1, 5.0 mL) was heated to 50 o C for 3 h. After aqueous extractive workup and column chromatographic purification process (n-hexane/EtOAc, 1:1), 3-hydroxy-3-(1H-indol-3-yl)-1-methylindolin-2-one was obtained as a white solid, 340 mg (61%). A solution of 3-hydroxy-3-(1H-indol-3-yl)-1-methylindolin-2-one (278 mg, 1.0 mmol), 5-methyl-1H-indole (131 mg, 1.0 mmol), and p-TsOH . H 2 O (19 mg, 0.1 mmol) in CH 2 Cl 2 (2.0 mL) was stirred at room temperature for 1 h. After aqueous extractive workup and column chromatographic purification process (n-hexane/EtOAc, 2:1), 5,1′-dimethyl-1H,1’H,1”H-[3,3′;3′,3”]terindol-2′-one was obtained as a white solid, 348 mg (89%). To a stirred solution of 5,1′-dimethyl-1H,1’H,1”H-[3,3′;3′,3”]terindol-2′-one (196 mg, 0.5 mmol) in DMF (3.0 mL) was added t-BuOK (125 mg, 1.1 mmol) and iodomethane (158 mg, 1.1 mmol) successively at 0 o C. The reaction mixture was stirred at room temperature for 3 h. After aqueous extractive workup and column chromatographic purification process (n-hexane/EtOAc, 3:1), compound 1g was obtained as a white solid, 156 mg (74%). Compound 1h was synthesized similarly, and the spectroscopic data of unknown compounds 1g and 1h are as follows. Compound 1g: 74%; pale yellow solid, mp 202-204 o C; IR (KBr) 1716, 1490, 1469, 1370, 1340 cm -1 ; 1 H NMR (CDCl 3 , 500 MHz) 1gNOMeNNMeMeMe6 delta 2.31 (s, 3H), 3.35 (s, 3H), 3.66 (s, 3H), 3.69 (s, 3H), 6.79 (s, 1H), 6.86 (s, 1H), 6.93 (t, J = 7.5 Hz, 1H), 6.95-7.05 (m, 3H), 7.12 (s, 1H), 7.13-7.19 (m, 2H), 7.21 (d, J = 8.1 Hz, 1H), 7.27 (d, J = 8.1 Hz, 1H), 7.33 (t, J = 7.7 Hz, 1H), 7.43 (d, J = 7.2 Hz, 1H); 13 C NMR (CDCl 3 , 125 MHz) delta 21.6, 26.6, 32.75, 32.77, 52.7, 108.0, 108.9, 109.2, 113.0, 113.7, 118.9, 121.12, 121.13, 121.4, 122.6, 123.2, 125.3, 126.3, 126.5, 127.9, 128.0, 128.8, 128.9, 134.2, 136.2, 137.7, 142.9, 177.8; MALDI-TOF m/z 420 [M+H] + .
According to the analysis of related databases, 2058-74-4, the application of this compound in the production field has become more and more popular.
Reference:
Article; Seo, Da Young; Kim, Gieun; Jo, Hwi Yul; Kim, Jae Nyoung; Bulletin of the Korean Chemical Society; vol. 39; 4; (2018); p. 587 – 590;,
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