Discovery of 496-12-8

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 496-12-8.

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 496-12-8, name is Isoindoline, This compound has unique chemical properties. The synthetic route is as follows., name: Isoindoline

General procedure: A mixture of tert-butyl (2-amino-1-(thiophen-3-yl)ethyl)(methyl)carbamate (33) (310 mg, 1.21 mmol) and N,N-diisopropylethylamine (300 muL, 1.73 mmol) in CH2Cl2 (15 mL) was purged with argon and cooled to 0 C. A solution of 4-nitrophenylchloroformate (244 mg, 1.21 mmol) in CH2Cl2 (5 mL) was added, and resulting reaction mixture was stirred at – 70 C for 30 min. After this time, 5-fluoroisoindoline hydrochloride (150 mg, 0.86 mmol) was added, followed by N,N-diisopropylethylamine (450 muL, 2.60 mmol). The resulting mixture was stirred for 20 h at room temperature. A saturated NaHCO3 solution (10 mL) was added, and the resulting suspension was extracted with CH2Cl2 (3 x15 mL). The combined organic extracts were washed with water (30 mL), then with a brine solution (20 mL) and dried over solid anhydrous Na2SO4. After filtration, the volatiles were removed in vacuo, and the residue was purified by flash chromatography using eluent from CH2Cl2 to CH2Cl2/MeOH (1:1), then reverse phase chromatography using eluent from H2O/MeCN (9:1) MeCN, to give tert-butyl (2-(5-fluoroisoindoline-2-carboxamido)-1-(thiophen-3- yl)ethyl)(methyl)carbamate (34) (150 mg, 41% yield). 300 MHz 1H-NMR (CDCl3, ppm): 7.32 (dd, J=5.0, 2.9 Hz, 1H) 7.24-7.14 (m, 2H) 7.05-6.91 (m, 3H) 5.63-5.41 (m, 1H) 5.09- 4.91 (m, 1H) 4.68 (s, 2H) 4.64 (s, 2H) 4.15-3.88 (m, 1H) 3.77-3.57 (m, 1H) 2.56 (s, 3H) 1.45 (s, 9H); ESI-MS (m/z): 420 [M+H]+; melting point: 182-184 C. Isoindoline (500 mg, 4.20 mmol) and tert-butyl (2-amino-1-phenylethyl)(methyl) carbamate (36) were reacted in CH2Cl2 using procedure described for compound (34) to obtain tert-butyl (2-(isoindoline-2-carboxamido)-1-phenylethyl)(methyl)carbamate (37) (1.49 g, 90% yield). 400 MHz 1H-NMR (CDCl3, ppm): 7.41-7.33 (m, 2H) 7.33-7.29 (m, 2H) 7.29- 7.23 (m, 5H) 5.62-5.41 (m, 1H) 5.19-5.00 (m, 1H) 4.71 (s, 4H) 4.19-3.93 (m, 1H) 3.84-3.62 (m, 1H) 2.55 (s, 3H) 1.46 (s, 9H); ESI-MS (m/z): 396 [M+H]+.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 496-12-8.

Reference:
Patent; MEBIAS DISCOVERY LLC; TOUNGE, Brett A.; BAYOUMY, Shariff; KUO, Lawrence C.; DAX, Scott; (93 pag.)WO2018/45229; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem