Category: 84807-26-1

Synthetic Route of 84807-26-1,Some common heterocyclic compound, 84807-26-1, name is 4-Nitroindoline, molecular formula is C8H8N2O2, 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.

1-{1-[6-(4-nitro-2,3-dihydroindole-1-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3-dihydro-imidazo[4,5-b]pyridin-2-one 150 mg (0.470 mmol) TBTU were added to 150 mg (0.44 mmol) 6-[4-(2-oxo-2,3-dihydro-imidazo[4,5-b]pyridin-1-yl)-piperidin-1-yl]-pyrimidine-4-carboxylic acid, 75 mg (0.46 mmol) 4-nitro-2,3-dihydro-1H-indole, 100 muL (0.712 mmol) triethylamine in 1.5 mL DMF and the mixture was stirred overnight at RT. The reaction mixture was poured onto 30 mL water. The aqueous phase was extracted with DCM (3*20 mL). The combined organic phases were dried on magnesium sulphate, filtered and evaporated down i. vac. The residue was dissolved in 3 mL DMF, filtered through a syringe filter and purified by preparative HPLC. The product fractions were combined and lyophilised. Yield: 30 mg (14% of theoretical) ESI-MS: m/z=487 (M+H)+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Nitroindoline, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/195954; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 84807-26-1, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 84807-26-1 as follows.

General procedure: To a solution of 6-nitroindoline (13) (590 mg, 3.6 mmol), tert-butyl 4-oxopiperidine-1-carboxylate (860 mg, 4.3 mmol) in acetic acid (10.0 mL) was added sodium triacetoxyborohydride (1.14 g, 5.4 mmol) at 0C and the reaction mixture was stirred for 1 hr at this temperature and then heated to room temperature overnight. After the reaction completed, water was added to the the mixture and the mixture was extracted with CH2Cl2. The organic phase was washed with water and saturated NaHCO3, dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure to afford the crude product, which was purified by column chromatography to give the tert-butyl 4-(6-nitroindolin-1-yl) piperidine-1-carboxylate (14) 0.92 g, yield: 73.6%.

According to the analysis of related databases, 84807-26-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Tian, Jinlong; Sun, Nannan; Yu, Mingcheng; Gu, Xianfeng; Xie, Qiong; Shao, Liming; Liu, Jin; Liu, Li; Wang, Yonghui; European Journal of Medicinal Chemistry; vol. 167; (2019); p. 37 – 48;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem