Category: 675109-26-9

675109-26-9, A common compound: 675109-26-9, name is 6-Bromoisoindolin-1-one, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

General procedure: Bromoisoindolin-1-one (2.0 g, 9.43 mmol) was dissolved with warming in DMF (150 mL),then cooled to 0C. NaH (415 mg, 10.4 mmol) was added and the mixture stirred under N2 at 0C for 0.5 h. Methyl iodide (0.65 mL, 10.4 mmol) was added dropwise and the reaction allowed to warm to room temperature and stir for another I h. A small quantity of water was added to quench the reaction then the DMF removed under reduced pressure to give an oily yellow residue which was dissolved in EtOAc (150 mL). This solution waswashed with water (3×100 mL), brine (100 mL) and dried (Na2SO4)., Removal of the solvent under reduced pressure gave a solid which was purified by filtration through a plug of silica gel (10% acetone/CH2C12 as eluant). The title compound was isolated as a very pale yellow crystalline solid (1.64 g, 80%). ? H NMR [400 MHz, (CD3)2S0] oe 7.85 (dd, J= 1.5, 0.6 Hz, 1 H), 7.66 (dd, J= 8.0, 1.7 Hz, 1 H), 7.59 (d, J- 8.0 Hz, I H), 4.46 (s,2 H), 3.05 (s, 3 H). LRMS (APCI) calcd for C9H8BrNO 226, 228 (MH), found 226, 228.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 6-Bromoisoindolin-1-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PETER MACCALLUM CANCER INSTITUTE; SPICER, Julie Ann; DENNY, William Alexander; MILLER, Christian Karl; O’CONNOR, Patrick David; HUTTUNEN, Kristiina; TRAPANI, Joseph A.; HILL, Geoff; ALEXANDER, Kylie; WO2014/28968; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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

675109-26-9, name is 6-Bromoisoindolin-1-one, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 675109-26-9

To a solution of 6-bromoisoindolin-l-one (2.418 g, 11.4 mmol) in DMF (57 mL) at 0 C. was added NaH (0.547 g, 13.68 mmol). The resulting dark suspension was allowed to stir for 60 min before addition of PMBC1 (1.86 mL, 13.68 mmol). The reaction was then allowed to stir at room temperature for 3 hours. The crude was diluted by EtOAc, washed with water and brine. The organic layers were dried over Na2SO4 and concentrated. The residue was purified by chromatography on silica gel using 0->50% EtOAc in hexanes to afford 3.18 g yellow solid as compound 2 (84% yield). 1H NMR (400 MHz, Chloroform-d) delta8.04 (d, J=1.9 Hz, 1H), 7.65 (dd, J=8.0, 1.9 Hz, 1H), 7.25 (d, J=8.6 Hz, 2H), 6.89 (d, J=8.6 Hz, 2H), 4.75 (s, 2H), 4.22 (s, 2H), 3.82 (s, 3H).

Statistics shows that 675109-26-9 is playing an increasingly important role. we look forward to future research findings about 6-Bromoisoindolin-1-one.

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; Wang, Guoqiang; He, Jing; Wang, Bin; Shen, Ruichao; Granger, Brett; Or, Yat Sun; US2019/62310; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

675109-26-9, The chemical industry reduces the impact on the environment during synthesis 675109-26-9, name is 6-Bromoisoindolin-1-one, I believe this compound will play a more active role in future production and life.

Preparation 117: 6-bromo-2-(cyclopropylmethyl)-2,3-dihydro-1 H-isoindol-1 -one (1710) (1711) A stirred solution of 6-bromo-2,3-dihydro-1 H-isoindol-1 -one (350 mg, 1.65 mmol) and cyclopropylmethyl bromide (0.198 muIota_, 1.98 mmol) in DMF (6 mL) was cooled in an ice bath under nitrogen. Then NaH (99 mg, 2.48 mmol) was added in portions. The reaction was stirred for 1 hour and then quenched with NH4CI (sat., aq.). The mixture was extracted with IPA:CHCI3 (1 :3, x3). The combined organic layers were washed with brine, dried over MgS04, filtered and concentrated under vacuum to yield the title compound as a brown oil (~30 % pure) which was used crude. MS: [M+H]+ = 266/268.

The chemical industry reduces the impact on the environment during synthesis 6-Bromoisoindolin-1-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; BERDINI, Valerio; BUCK, Ildiko Maria; DAY, James Edward Harvey; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; HOWARD, Steven; MURRAY, Christopher William; NORTON, David; O’REILLY, Marc; WOOLFORD, Alison Jo-Anne; COOKE, Michael Liam; COUSIN, David; ONIONS, Stuart Thomas; SHANNON, Jonathan Martin; WATTS, John Paul; (867 pag.)WO2017/68412; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem