Synthetic Route of 1035235-27-8, A common heterocyclic compound, 1035235-27-8, name is tert-Butyl 4-bromoisoindoline-2-carboxylate, molecular formula is C13H16BrNO2, 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.
Step a. To a stirred solution of tert-butyl 4-bromoisoindoline-2-carboxylate (Intermediate 1, 0.35 g, 1.185 mmol) in 1,4-dioxane: water (4: 1; 20 ml) was added Cs2C03 (0.77 g, 2.371 mmol) at rt under nitrogen. The reaction was purged with nitrogen for 15 min. Pd(PPh3)4 (0.14 g, 0.118 mmol) was added to the reaction mixture and purged with nitrogen for 10 min. 3- (Methoxycarbonyl)phenylboronic acid (CAS Number 99769-19-4; available from Combi Blocks) (0.26 g, 1.422 mmol) was added to the reaction mixture. The reaction mixture was heated at 80C for 24 h. The resulting reaction mixture was cooled to rt, poured into water (20 ml) and extracted with EtOAc (3 x 50). The combined organic phase was washed with brine (80 ml). The organic phase was separated, dried over Na2S04, filtered and concentrated under reduced pressure. The resulting crude material was purified by flash chromatography (5% EtOAc in hexane) yielding tert-butyl 4-(3- (methoxycarbonyl)phenyl)isoindoline-2-carboxylate (0.33 g, 0.932 mmol). LCMS: Method A, 2.782 min, MS: ES+ 298.4 (M-56); 1H NMR (400 MHz, CDC13) delta ppm 8.04 – 8.11 (m, 2 H), 7.62 (d, J=7.2 Hz, 1H), 7.49 – 7.58 (m, 2 H), 7.40 (t, J=7.2 Hz, 1H), 7.31 – 7.33 (m, 1H), 4.69 – 4.79 (m, 4 H), 3.95 (s, 3 H), 1.53 (s, 9 H).
The synthetic route of 1035235-27-8 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; MISSION THERAPEUTICS LIMITED; GIBSON, Karl Richard; JONES, Alison; KEMP, Mark Ian; MADIN, Andrew; STOCKLEY, Martin Lee; WHITLOCK, Gavin Alistair; WOODROW, Michael D; (241 pag.)WO2017/158388; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem