Reference of 19155-24-9, These common heterocyclic compound, 19155-24-9, name is 3,3-Dimethylindolin-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.
To a mixture of 3,3-dimethyloxindole 41 (150 mg,0.93 mmol, 1.00 equiv) and Cs2CO3 (606 mg, 1.86 mmol, 2.00 equiv) in THF (4.70mL) was added o-nitrobenzyl bromide (302 mg, 1.40 mmol, 1.50 equiv). Thereaction mixture was stirred overnight. Then, the reaction mixture was extracted withEtOAc (3 x 6 mL) and washed with brine. The combined organic phases were driedover MgSO4 and concentrated in vacuo. The residue was purified by columnchromatography (1:4 ? 1:2 EtOAc:hexanes) on silica gel to afford N?2-nitrobenzyl-3,3-dimethyloxindole 3a (258 mg, 93percent yield).Rf = 0.35 (1:2 EtOAc:hexanes); 1H NMR (500 MHz, CDCl3) delta 8.16 (dd, J = 8.1, 1.4Hz, 1H), 7.51 (td, J = 7.6, 1.4 Hz, 1H), 7.44 (dddt, J = 8.1, 7.4, 1.4, 0.7 Hz, 1H), 7.28(ddd, J = 7.3, 1.3, 0.6 Hz, 1H), 7.17 (td, J = 7.7, 1.3 Hz, 1H), 7.12 (dq, J = 7.8, 1.0Hz, 1H), 7.09 (td, J = 7.5, 1.1 Hz, 1H), 6.61 (dt, J = 7.8, 0.8 Hz, 1H), 5.33 (d, J = 0.8Hz, 2H), 1.48 (s, 6H); 13C NMR (126 MHz, CDCl3) delta 181.8, 148.2, 141.4, 135.8,134.2, 132.0, 128.5, 128.0, 127.6, 125.7, 123.2, 122.8, 108.8, 77.2, 44.5, 41.2, 24.8;IR (Neat Film NaCl) 2968, 1721, 1615, 1524, 1489, 1385, 1338, 1177, 1008, 858, 761cm-1; HRMS (MM: ESI-APCI+) m/z calc?d for C17H17N2O3 [M+H]+ : 297.1234;found: 297.1236.1 Vu, A. T.; Cohn, S. T.; Zhang, P.; Kim, C. Y. Mahaney, P. E.; Bray, J. A.; Johnston, G. H.; Koury, E.J.; Cosmi, S. A.; Deecher, D. C.; Smith, V. A.; Harrison, J. E.; Leventhal, L.; Whiteside, G. T.;Kennedy, J. D.; Trybulski, E. J. J. Med. Chem. 2010, 53, 2051?2062.NHOo-nitrobenzyl bromideCs2CO3THF, 23 °C(93percent yield)NOO2N4 3a
The synthetic route of 19155-24-9 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Han, Seo-Jung; Fernando De Melo, Gabriel; Stoltz, Brian M.; Tetrahedron Letters; vol. 55; 47; (2014); p. 6467 – 6469;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem