Related Products of 201940-08-1,Some common heterocyclic compound, 201940-08-1, name is tert-Butyl 5-bromoisoindoline-2-carboxylate, molecular formula is C13H16BrNO2, 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 suspension of tert-butyl 5-bromo-2-(tert-butoxycarbonyl)isoindoline (1.2 g, 4 mmol) and bis(pinacolato)diboron (2 g, 8 mmol) in DMSO (20 mL) was added AcOK (1.6 g, 16 mmol), followed by Pd(dppf)Cl2-CH2Cl2 (327 mg, 0.4 mmol) under N2 atmosphere. The reaction was heated at 90 C for 12 h, then cooled to rt and poured into EtOAc/H20 (300 mL/100 mL). The separatedorganic phase was washed with brine (100 mL), dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (v/v) =20/1) to give the title compound as yellow oil (1 g, 73%). MS (ESI, pos. ion) m/z: 290.2 [M-56+l ; NMR (400 MHz, CDC13) delta (ppm): 7.68-7.74 (m, 2H), 7.23-7.30 (m, 1H), 4.64-4.70 (m, 4H), 1.53 (s, 9H), 1.36 (s, 12H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl 5-bromoisoindoline-2-carboxylate, its application will become more common.
Reference:
Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD; XI, Ning; WANG, Ruyong; WANG, Liang; WO2014/89324; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem