Electric Literature 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.
To a stirred solution of tert-butyl 5-bromoisoindoline-2-carboxylate (32-1) (300 mg, 1.00 mmol) in dioxane and water (2.5 ml), was added 2,6-bis(benzyloxy)-3-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)pyridine (25-1) (459 mg, 1.10 mmol) and potassium phosphate (636 mg, 3.00 mmol) at room temperature. The reaction mixture was purged with argon for 5 minutes followed by addition of Pd(dppf)Cl2-DCM (40.8 mg, 50.0 mumol) at room temperature. The reaction mixture was heated to reflux overnight. After completion of reaction (monitored by TLC Rf = 0.4 in 20% ea/ hexane and LCMS), the reaction mixture was filtered and concentrated. The crude residue was purified by flash column (elution with 15 % EtOAc/Hexanes) to afford tert-butyl 5-(2,6- bis(benzyloxy)pyridin-3-yl)isoindoline-2-carboxylate (32-2) (330 mg, 648 mumol, 64.9 %) as a gummy liquid.1H NMR (400 MHz, DMSO-d6) delta 7.65-7.63 (m, 1H), 7.45-7.44 (m, 2H), 7.40-7.38 (m, 2H), 7.36-7.21 (m, 7H), 7.19 (m, 1H), 6.54 (m, 1H), 5.37 (br s, 4H), 4.63-4.60 (m, 2H), 4.43 (br s, 2H), 1.44-1.39 (m, 9H).
The synthetic route of 1035235-27-8 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; HE, Minsheng; LAZARSKI, Kiel; VEITS, Gesine, Kerstin; VORA, Harit, U.; (794 pag.)WO2017/197046; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem