Application of 552330-86-6, A common heterocyclic compound, 552330-86-6, name is 5-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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.
Prepared using method described in Example 4, step (a) with the solution being initially irradiated for 90 min and then a further 90 min using 5-cyclopropyl-6-methyl-7-(tetramethyl- 1 ,3,2-dioxaborolan-2yl)-oxazolo[4,5-c]quinolin-4-one (Intermediate D) and 5-bromo-2,3- dihydro-1 H-isoindol-1-one. Chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1 , 1 ‘- biphenyl)[2-(2’-amino-1 , 1 ‘-biphenyl)]palladium(ll) (10% mmol) was used as catalyst and .2- dicyclohexylphosphino-2′,4′,6’-triisopropylbiphenyl (10% mmol) as ligand. Column chromatography was carried out, eluting with 0-20% MeOH in DCM. 1 H NMR (Method A) (CDCb): delta ppm 8.10 (s, 1 H), 7.99 (d, J = 7.8 Hz, 1 H), 7.81 (d, J = 7.9 Hz, 1 H), 7.53 (d, J = 8.0 Hz, 1 H) 7.50 (s, 1 H), 7.28 (s, 1 H), 6.22 (s, 1 H), 4.56 (s, 2H), 3.69- 3.61 (m, 1 H), 2.54 (s, 3H), 1.33 (d, J = 6.8 Hz, 2H) 0.74 – 0.66 (m, 2H); LC-MS (Method D) 372.0 [M+H]+; RT 1.96 min
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; REDX PHARMA PLC; HUXLEY, Anthony; KIRK, Ralph; RATCLIFFE, Andrew; LYTH, David; (112 pag.)WO2017/46605; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem