Some common heterocyclic compound, 675109-26-9, name is 6-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. 675109-26-9
(6-( 1 – (and 2-)(4-methoxybenzyl)-2H-tetrazol-5 -yl)-4′-methyl-5-sulfamoyl- [ 1 , 1 ‘- biphenyl]-3-yl)boronic acid (40 mg, 0.083 mmol) and 6-bromoisoindolin-l-one (19.47 mg, 0.092 mmol) was suspended in ethanol (835 mu) and potassium phosphate tribasic (250 mu, 0.250 mmol). The reaction mixture was sparged with 2 for 5 min. 1 , l’-bis(di-tert- butylphosphino)ferrocene palladium dichloride (5.44 mg, 8.35 muiotaetaomicron) was added and the reaction mixture micro waved at 1 10C for 90 min. The crude reaction mixture was diluted with EtOAc and water. The aqueous phase was extract with EtOAc (x2), then the combined extracts were washed with brine, dried over Na2S04, filtered, and concentrated. The reaction mixture was purified by reverse phase HPLC on a Cis column and then eluted with 10% to 100% MeCN in water. The major UV active material was lyopholized to provide a white solid that was utilized directly in the deprotection. LC-MS: calculated for C3oH26N604S 566.2; observed m/e: 467.5 (M+H)+. The resulting solid was dissolved in TFA and heated to 45C overnight, then concentrated. The residue was purified by reverse phase HPLC on a Cis column eluted with 0% to 80% MeCN in water. The major UV active material was lyopholized to provide 4′-methyl-5- (l-oxoisoindolin-5-yl)-2-(2H-tetrazol-5-yl)-[l, l’-biphenyl]-3-sulfonamide. LC-MS: calculated for C22H18N603S 446.1 ; observed m/e: 447.4 (M+H)+; 1H NMR delta (ppm) (DMSO): 8.72 (s, 1H), 8.44 (s, 1H), 8.16 (s, 1H), 8.12 (d, 1H), 8.05 (s, 1H), 7.77 (d, 1H), 7.60 (s, 2H), 7.11-7.05 (m, 4H), 4.48 (s, 2H), 2.27 (s, 3H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 675109-26-9, its application will become more common.
Reference:
Patent; MERCK SHARP & DOHME CORP.; MANDAL, Mihir; TANG, Haifeng; XIAO, Li; SU, Jing; LI, Guoqing; YANG, Shu-Wei; PAN, Weidong; TANG, Haiqun; DEJESUS, Reynalda; HICKS, Jacqueline; LOMBARDO, Matthew; CHU, Hong; HAGMANN, William; PASTERNAK, Alex; GU, Xin; JIANG, Jinlong; DONG, Shuzhi; DING, Fa-Xiang; LONDON, Clare; BISWAS, Dipshikha; YOUNG, Katherine; HUNTER, David, N.; ZHAO, Zhiqiang; YANG, Dexi; WO2015/112441; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem