Application of 1168150-46-6, A common heterocyclic compound, 1168150-46-6, name is (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate, molecular formula is C18H15NO4, 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.
General procedure: A mixture of intermediate (3a, 3b, 6a, 6b, 10a, 10b, 11a-d, and14a-g, 1.5 mmol) and methyl (E)-3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate (1.5 mmol) in methanol (10 mL) wasstirred under reflux for 5-10 h. When TLC showed the completionof the reaction, the solution was cooled to room temperature. Theprecipitate was filtered off to give a crude product, which wasrecrystallized from methanol to provide the target compounds. 4.1.12.1. Methyl (Z)-3-(((2-((dimethylamino)methyl)benzo[d]oxazol-6-yl)amino)(phenyl)methylene)-2-oxoindoline-6-carboxylate (A1).Yellow solid. Yield: 42%. Mp: 298.2-301.7 C. 1H NMR (400 MHz,DMSO-d6)delta 12.18 (s, 1H, NH), 10.92 (s, 1H, NH), 7.63e7.54 (m, 3H,ArH), 7.48 (dd, J = 7.7, 1.4 Hz, 2H, ArH), 7.41 (d, J= 1.3 Hz, 1H, ArH),7.18 (dd, J = 8.2, 1.5 Hz, 1H, ArH), 6.67 (d, J= 8.3 Hz, 1H, ArH), 6.41(dd, J= 8.4, 2.4 Hz, 1H, ArH), 6.27 (d, J = 2.4 Hz, 1H, ArH), 5.78 (d,J = 8.2 Hz, 1H, ArH), 4.66 (s, 2H, CH2), 3.76 (s, 3H, OCH3), 2.95 (s, 6H,CH3). 13C NMR (101 MHz, DMSO-d6)delta 170.60, 166.93, 159.24, 156.11,144.40, 136.30, 133.69, 132.77, 132.51, 130.74, 129.86, 129.67, 128.80,123.94, 123.38, 121.84, 117.91, 117.36, 110.33, 109.83, 96.95, 60.48,56.49, 52.21. HRMS (ESI) for C27H24N4O4 [M+H]+, calcd: 469.1870,found: 469.1873.
The synthetic route of 1168150-46-6 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Qin, Mingze; Tian, Ye; Sun, Xiaoqing; Yu, Simiao; Xia, Juanjuan; Gong, Ping; Zhang, Haotian; Zhao, Yanfang; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 492 – 502;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem