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 (100 mg,0.62 mmol, 1.00 equiv) and Cs2CO3 (403 mg, 1.24 mmol, 2.00 equiv) in THF (3.10mL) was added m-nitrobenzyl bromide (335 mg, 1.55 mmol, 2.50 equiv). Thereaction mixture was stirred overnight. Then, the reaction mixture was extracted withEtOAc (3 x 4 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?3-nitrobenzyl-3,3-dimethyloxindole 3b (170 mg, 92percent yield).Rf = 0.35 (1:2 EtOAc:hexanes); 1H NMR (500 MHz, CDCl3) delta 8.16 ? 8.11 (m, 2H),7.60 (ddt, J = 7.7, 1.8, 0.9 Hz, 1H), 7.53 ? 7.48 (m, 1H), 7.26 ? 7.24 (m, 1H), 7.17 (td,J = 7.7, 1.3 Hz, 1H), 7.07 (td, J = 7.5, 1.0 Hz, 1H), 5.01 (s, 2H), 1.46 (s, 6H); 13CNMR (126 MHz, CDCl3) delta 181.7, 148.6, 141.1, 138.5, 135.9, 133.3, 130.1, 127.9,123.2, 122.9, 122.8, 122.2, 108.7, 77.2, 44.4, 43.0, 24.7; IR (Neat Film NaCl) 2969,1652, 1538, 1348, 1011, 933, 761; HRMS (MM: ESI-APCI+) m/z calc?d forC17H17N2O3 [M+H]+ : 297.1234; found: 297.1241.
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