Category: 944937-53-5

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. 944937-53-5, name is 6-Bromo-1H-pyrrolo[3,2-b]pyridine, molecular formula is C7H5BrN2, 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. name: 6-Bromo-1H-pyrrolo[3,2-b]pyridine

To an ice-cooled suspension of 6-bromo- 1H-pyffolo[3,2-b]pyridine (7.0 g, 35 mmol)in N,N-dimethylformamide (100 mL) was slowly added a solution of sodium hydride (2.12 g,88.28 mmol, 60% in mineral oil) in N,N-dimethylformamide (20 mL). After 30 mm at 0 C,a solution of 2-(1-chloroethyl)pyridine (5.0 g, 35 mmol) in N,N-dimethylformamide (20 mL)was slowly added. The mixture was then warmed to room temperature. After 16 h, saturatedaqueous ammonium chloride solution (20 mL) was slowly added to the reaction mixture, and the resulting solution was concentrated in vacuo. The resulting residue was purified by flash column chromatography (1 0-30% ethyl acetate in petroleum ether) to afford 6-bromo- 1 -(1 -(pyridin-2-yl)ethyl)- 1 H-pyrrolo [3,2-b] pyridine (6.0 g, 56% yield). 1 H NMR(400 MHz, Chloroform-d) oe: 8.61 (d, I = 4.4 Hz, 1 H), 8.47 (d, I = 2.0 Hz, 1 H), 7.70 (s, 1 H),7.62-7.57 (m, 2 H), 7.21 -7.18 (m, 1 H), 6.81-6.76 (m, 2 H), 5.66-5.61 (m, 1 H), 2.00 (d, I = 7.2 Hz, 3 H).

With the rapid development of chemical substances, we look forward to future research findings about 944937-53-5.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; LYSSIKATOS, Joseph P.; LIU, Wen; SIU, Michael; ESTRADA, Anthony; PATEL, Snahel; LIANG, Guibai; HUESTIS, Malcolm; CHEN, Kevin; WO2015/91889; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 944937-53-5, name is 6-Bromo-1H-pyrrolo[3,2-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 6-Bromo-1H-pyrrolo[3,2-b]pyridine

To a mixture of 6-bromo-lH-pyrrolo[3,2-b]pyridine (0.985 g, 5 mmol, 1 eq) in N,N- dimethylformamide (25ml) was added cesium carbonate (1.79 g, 5.5 mmol, 1.1 eq), followed by (1,4,4- trifluorocyclohexyl)methyl trifluoromethanesulfonate (1.50 g, 5 mmol, 1 eq). The mixture was stirred at 70 C for five hours. The mixture was quenched with water, and extracted with ethyl acetate which was washed with water and brine. The organic layer was dried over sodium sulfate, filtered and concentrated down. The sample was purified by flash chromatography eluting with 40% ethyl acetate in hexane, then triturated with hexanes to provide 1.63 g (93.9%) of product as a solid (24, 1.63 g, 93.9%), MS (ESI) [M+H+]+ = 347.0, 349.0.

With the rapid development of chemical substances, we look forward to future research findings about 944937-53-5.

Reference:
Patent; ZHANG, Jiazhong; BUELL, John; CHAN, Katrina; IBRAHIM, Prabha, N.; LIN, Jack; PHAM, Phuongly; SHI, Songyuan; SPEVAK, Wayne; WU, Guoxian; WU, Jeffrey; WO2014/145051; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 944937-53-5, name is 6-Bromo-1H-pyrrolo[3,2-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 6-Bromo-1H-pyrrolo[3,2-b]pyridine

To a solution of 6-Bromo-lEta-pyrrolo[3,2- b]pyridine (1.9 g, 10 mmol) in 20 mL of DMF at 00C was added NaH (60% in oil, 0.49 g, 12 mmol) in three portions. The mixture was stirred at room temperature for 30 min. A solution of NH2Cl in Et2O (prepared according to the procedure described in J. Org. Chem. 2004, 1371 : -0.15 M, 80 mL) was added at -200C. The mixture was warmed up to room temperature for 15 min and was poured into a saturated solution of thiosulfate and ammonium chloride, and extracted with ethyl acetate. The organic layer was concentrated and the residue washed with small amount of ethyl acetate to give pink solid (1.3 g, 62% yield)

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 944937-53-5, 6-Bromo-1H-pyrrolo[3,2-b]pyridine.

Reference:
Patent; ARIAD PHARMACEUTICALS, INC.; QI, Jiwei; WANG, Yihan; LI, Feng; SHAKESPEARE, William, C.; KOHLMANN, Anna; DALGARNO, David, C.; ZHU, Xiaotian; WO2010/68292; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 944937-53-5, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.944937-53-5, name is 6-Bromo-1H-pyrrolo[3,2-b]pyridine, molecular formula is C7H5BrN2, molecular weight is 197.03, as common compound, the synthetic route is as follows.

General procedure: To a 20 ml or 40 ml viale quipped with a stir bar was added photocatalyst, nitrogen nucleophile, iodomesitylene dicarboxylate, copper salt, and ligand. Dioxane was added followed by addition of the base. The solution was sonicated for 1-3 min until it became homogeneous. Next, the solution was degassed by sparging with nitrogen for 5-10 min before sealing with Parafilm. The reaction was stirred and irradiated using two 34-W blue LED lamps (3 cm away, with cooling fan to keep the reaction at room temperature) for 1 h. The reaction mixture was removed from the light, cooled to ambient temperature, diluted with water (15 ml) and ethyl acetate (25 ml), and the aqueous layer was extracted with ethyl acetate (3 ¡Á 25 ml). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel to afford the desired decarboxylative C-N coupling product. For aniline substrates, a solution of these nitrogen nucleophiles in dioxane was used; additionally, if the iodomesitylene dicarboxylate is a liquid, its solution in dioxane was used.

Statistics shows that 944937-53-5 is playing an increasingly important role. we look forward to future research findings about 6-Bromo-1H-pyrrolo[3,2-b]pyridine.

Reference:
Article; Liang, Yufan; Zhang, Xiaheng; MacMillan, David W. C.; Nature; vol. 559; 7712; (2018); p. 83 – 88;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 944937-53-5, name is 6-Bromo-1H-pyrrolo[3,2-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 6-Bromo-1H-pyrrolo[3,2-b]pyridine

To a soution of 6-bromo-1 H-pyrroo[3,2-b]pyridine (300 mg, 1.5 mmo) inDMF (2 mL), at 0 C, was added NaH (183 mg, 4.6 mmoL 60% dispersion in oi?). The reaction mixture was warmed to room temperature and stirred for 10 minutes and then cooed to 0 C and 3-(choromethy 5-methyisoxazoe (240 mg, 1.8 mmo) was added. The mixture was stirred at 0 C for 10 minutes then warmed to room temperature and stirred for 4 hours. Water was addedand the reaction mixture was extracted with EtOAc. The combined organicayers were dried (MgSO4), fi[tered and evaporated. Purification (FCC, Si02,0-100% EtOAc in hexanes) gave the tiUe compound (407 mg, 92%). 1H NMR(400 MHz, DMSO-d6) oe 8.41 (d, J = 2.0 Hz, I H), 8.26 (dd, J = 2.0, 0.9 Hz, I H),7.78 (d, J = 3.4 Hz, I H), 6.64 (dd, J = 3.3, 1.0 Hz, I H), 6.07 (d, J = 1.0 Hz,1 H), 5.52 (s, 2H), 2.33 (d, J = 0.9 Hz, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 944937-53-5.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; CHROVIAN, Christa C.; LETAVIC, Michael A.; RECH, Jason C.; SOYODE-JOHNSON, Akinola; WALL, Jessica L.; (533 pag.)WO2017/7938; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 944937-53-5, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 944937-53-5, name is 6-Bromo-1H-pyrrolo[3,2-b]pyridine. A new synthetic method of this compound is introduced below.

A solution of 6-bromo-1H-pyrrolo[3,2-¡ê]pyridine (54 kg from multiple batches based on wt % assay, 274 mol) in ethyl acetate from the previous step was distilled under vacuum at 45¡À5C to a volume of about 110 L (2L/kg) and then cooled to 25¡À5C. Dimethylcarbonate (33.0 kg, 367 mol) and Et3N (22.0 kg, 217 mol) were added and the mixture was distilled under vacuum at 50¡À5 C to a volume of about 85 L. N,N- dimethylformamide (82.5 kg, 1.6L/kg) was added and the mixture was distilled under vacuum at 50¡À5 C until no distillate was observed. The mixture was cooled to 25¡À5C, and dimethylcarbonate (165 kg, 1833 mol), Et3N (60.5 kg, 598 mol), and tetrabutylammonium bromide (11.0 kg) were added. The reaction mixture was heated to 88¡À5C. After 12 hours at 105-110C (jacket temperature), which corresponded to 83-85C reaction mixture temperature, HPLC analysis indicated 59.6% of the starting material remained. The jacket temperature was increased to 115-120C (corresponding to 84-87C reaction mixture temperature). After 18 hours at 115-120C (jacket temperature) HPLC analysis indicated 0.2% of the starting material remained. The mixture was cooled to 25C and then concentrated under vacuum at 55¡À5C to remove most of the dimethylcarbonate and Et3N. Next, the mixture was cooled to 25C and MTBE (340 kg) was added, followed by water (440 kg). The mixture was stirred for 30 minutes. Stirring was stopped and the mixture was left for 30 minutes for phase separation to occur. The aqueous phase was extracted with MTBE (2 x 209 kg). The MTBE phases were combined and washed with brine solution (286 kg). Activated charcoal (2.7 kg) was added to the organic phase, which was stirred for 1 hour and then filtered through a pad of Celite. The filter cake was washed with MTBE (55 kg). The organic layers were combined (750 kg, 6.45%> by HPLC-assay) and distilled to dryness to obtain the title compound as yellow oil (48.4 kg). The product was used directly in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,944937-53-5, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; CHANG, Edcon; NOTZ, Wolfgang Reinhard Ludwig; WALLACE, Michael B.; WO2014/11568; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem