Related Products of 2436-29-5,Some common heterocyclic compound, 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, molecular formula is C11H9NO3, 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 (R)-(l-amino-but-3-ynyl)-7-chloro-3-phenylamino-3H-quinazolin-4-one (4.60 g, 12.2 mmol) and diisopropylethylamine (DIPEA) (5.5 ml) in dichloromethane (60 ml) was added a solution of 3-(l,3-dioxo-l,3-dihydro-isoindol-2-yl)-propionaldehyde (2.45 g, 12.1 mmol) in dichloroethane (10 ml), followed by a solution of sodium triacetoxy borohydride (NaBH(OAc)3) (0.25M in dichloroethane, 100 ml). The reaction mixture was stirred at room temperature and the reaction progress was monitored by HPLC/MS. Upon completion, a saturated sodium carbonate solution (100 ml) was added. The resulted organic layer was collected and washed with brine solution. The solvent was removed and residue was purified by flash column to afford 2- {3-[(R)- 1 -(7-chloro-4-oxo-3-phenylamino-3,4-dihydro-quinazolin-2-yl)-but-3- ynylamino]-propyl}-isoindole-l,3-dione (6.1 g, 95%) as off-white solid. M.p. 78-80 0C. LCMS: m/e 526 [M+H]. 1H NMR (DMSO-d6): delta 9.09 (s, br, IH), 8.07 (d, J= 8.8 Hz, IH), 7.74 (m, IH), 7.83-7.76 (m, 5H), 7.58 (dd, J= 8.8 and 2.0 Hz, IH), 7.17 (t, J= 7.6 Hz, 2H), 6.83 (brm, IH), 6.65 (m, 2H), 4.1 and 4.0 (s,s, br, IH, rotomers), 3.6 (t, J= 6.8Hz, 2H), 2.75 (s, br, 1 H), 2.67- 2.52 (brm, 2H), 2.35 (brm, 2H), 1.67 (brm, 2H).
The synthetic route of 2436-29-5 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; ARQULE, INC.; WO2009/2808; (2008); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem