Some common heterocyclic compound, 552330-86-6, name is 5-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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. Computed Properties of C8H6BrNO
Step 3: 5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-isoindol-1-one 5-Bromo-2,3-dihydro-isoindol-1-one (230 mg, 1.08 mmol), bis(pinacolato)diboron (300 mg, 1.18 mmol), PdCl2dppf (25 mg, 31 mumol) and KOAc (320 mg, 3.26 mmol) are suspended in dioxane (4 ml), purged with nitrogen for 5 minutes and then heated at 85 C. overnight. The solvent is removed in vacuo and the residue partitioned between ethyl acetate and water. The aqueous layer is extracted three times with ethyl acetate and the combined organic phases are washed once with brine, filtered through anhydrous MgSO4 and evaporated. The solid residue is triturated with hexane and dried in vacuo to furnish the title compound (185 mg, 66%) as a grey solid. 1H-NMR (400 MHz, CDCl3) delta (ppm) 1.37 (s, 12H, 4*CH3), 4.45 (s, 2H, CH2), 6.38 (bs, 1H, NH), 7.87 (d, 1H, H), 7.93 (m, 2H, H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 552330-86-6, its application will become more common.
Reference:
Patent; Andrews, Martin James Inglis; Chambers, Mark Stuart; Van De Poel, Herve; Bar, Gregory Louis Joseph; US2009/286798; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem