76006-08-1 | Pyridine-derivatives

A new synthetic route of 5-Chloro-1H-pyrazolo[3,4-c]pyridine

The synthetic route of 76006-08-1 has been constantly updated, and we look forward to future research findings.

Electric Literature of 76006-08-1 , The common heterocyclic compound, 76006-08-1, name is 5-Chloro-1H-pyrazolo[3,4-c]pyridine, molecular formula is C6H4ClN3, 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.

To a solution of 5-chloro-lH-pyrazolo[3,4-c]pyridine (130 mg, 0.847 mmol) dissolved in N,N-dimethylformamide (5.00 ml) was added cesium carbonate (579 mg, 1.778 mmol) followed by tert-butyl 4-((methylsulfonyl)oxy)-2-oxopiperidine-l-carboxylate (273 mg, 0.931 mmol). The reaction mixture stirred at room temperature overnight. LC/MS analysis indicated that the desired product was not obtained. The reaction was heated to 65C and stirred overnight. The mixture was filtered through a 0.2 mm Millex syringe-driven filter unit, washed with methanol (2 x 6 mL) and concentrated to dryness under reduced pressure. The crude mixture was purified by reverse phase HPLC (10% to 90% AcetonitrileAVater + 0.1% TFA, over 10 minutes) to provide the desired product tert-butyl 4-(5-chloro-lH-pyrazolo[3,4-c]pyridin-l- yl)-2-oxopiperidine-l -carboxylate. LCMS (ESI) calc’d for C16H19CIN4O3 [M+H]+ = 351, found 351

The synthetic route of 76006-08-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; SILIPHAIVANH, Phieng; METHOT, Joey; LIPFORD, Kathryn Ann; MOLINARI, Danielle; SLOMAN, David, L.; WITTER, David; ZHOU, Hua; BOYCE, Christopher; HUANG, Xianhai; LIM, Jongwon; GUERIN, David; KARUNAKARAN, Ganesh Babu; BAKSHI, Raman Kumar; LIU, Ziping; FU, Jianmin; WAN, Zhilong; LIU, Wei; (216 pag.)WO2016/100050; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The important role of 76006-08-1

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,76006-08-1, its application will become more common.

Related Products of 76006-08-1, 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 76006-08-1 as follows.

To the solution of 5-chloro-lH-pyrazolo[3,4-c]pyridine (0.300 g, 1.95 mmol) in DMF (5 mL) at 0C was added NaH (0.234 g, 5.86 mmol, 60% dispersion in oil). After stirring for 5 min. tetrahydro-2H-pyran-4-yl methanesulfonate (0.632 g, 3.5 mmol) was added and the reaction mixture was heated at 100C for 5 h. TLC analysis indicated complete consumption of starting material and formation of 2 new spots. The reaction mixture was quenched by slow addition of ice-cold water (3 mL). The residue was bi-phased with water (15 mL) and ethyl acetate (25 mL). The aqueous layer was extracted with ethyl acetate (2 x 10 mL). The combined organic layers were washed with brine (1 x 15 mL), dried (anh. Na2S04) and concentrated under reduced pressure to furnish the title compound (0.230 g.). (0881) In step-1, the non-polar spot amongst the two new spots in the TLC, was the required regio-isomer (5). Both the regio-isomers obtained during N-alkylation were purified by flash column chromatography and the structure was confirmed by NMR and NOE experiments. MS (EI) calc’d for CnHi2N3OCl [M+H]+ Expected: 238; Found: 238; 1H NMR (400 MHz, CDC13) delta 9.06 (s, 1H), 8.15 (s, 1H), 7.79 (s, 1H), 4.90-4.78 (m, 1H), 4.24 (dd, 2H, J7 = 3.6 Hz, J2 = 11.2 Hz), 3.76-3.64 (m, 2H), 2.52-2.37 (m, 2H), 2.06 (dd, 2H, J7 = 2.4 Hz, J2 = 12.8 Hz)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,76006-08-1, its application will become more common.

Introduction of a new synthetic route about 76006-08-1

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 76006-08-1, 5-Chloro-1H-pyrazolo[3,4-c]pyridine.

Synthetic Route of 76006-08-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 76006-08-1, name is 5-Chloro-1H-pyrazolo[3,4-c]pyridine, molecular formula is C6H4ClN3, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a solution of 5-chloro-1H-pyrazolo[3,4-c]pyridine (15 g, 1 equiv) in DMF (150 mL) was added iodine (37.2 g, 1.5 equiv) and potassium hydroxide (13.7 g, 2.5 equiv) at 0 C. The reaction mixture was stirred at room temperature for 12 h and then diluted with 10% aqueous sodium thiosulfate (250 mL) and extracted with EtOAc. The combined organic extracts were washed with brine and then dried. The obtained solid (15 g) was slurried with MTBE, filtered and dried.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAK, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (905 pag.)WO2017/35353; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The origin of a common compound about 76006-08-1

According to the analysis of related databases, 76006-08-1, the application of this compound in the production field has become more and more popular.

5-bromo-2-methyl-2H-indazole (515 mg, 2.44 mmol) and (0404) bis[(tetrabutylammonium iodide)copper(I) iodide] (456 mg, 0.407 mmol) were combined in a reaction vessel, followed by5-chloro-lH-pyrazolo[3,4-c]pyridine (250 mg, 1.628 mmol), trans- N,N’-dimethylcyclohexane-l,2-diamine (0.257 ml, 1.628 mmol), and anhydrous K3P04 (691 mg, 3.26 mmol). This mixture was then evacuated and backfilled with N2 (3 times). Anhydrous degassed dioxane (20 ml) was added to this flask. This mixture was again evacuated and backfilled with N2 (3 times) and then as heated at 110C for 22h. LCMS showed a peak consistent with product. The reaction was diluted with EtOAc and water. The blue colored aqueous layer was separated from the green colored organic layer. The aqueous layer was extracted with EtOAc. The combined organics were filtered and concentrated. The residue was purified by column chromatography on silica gel (24g), eluting with 1-100 % EtOAc/hexanes to give 5-chloro-l-(2-methyl-2H-indazol-5-yl)-lH-pyrazolo[3,4-c]pyridine LCMS: M+H = 284

According to the analysis of related databases, 76006-08-1, the application of this compound in the production field has become more and more popular.