Category: 875781-43-4

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. 875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Bromo-5H-pyrrolo[2,3-b]pyrazine

General procedure: 2-Bromo-5H-pyrrolo[3,2-b]pyrazine(4; 0.471 g,2.39 mmol), 4-pyridylboronic acid (0.58 g, 4.72 mmol), dichloro 1,1′-bis(diphenylphosphino)ferrocenepalladium (II) dichloromethane adduct (0.097 g, 0.12 mmol), acetonitrile(3 mL) and 1M sodium carbonate (3 mL) were placed in a 10 mL CEM microwavevial. The vial was capped and irradiated in a CEM microwave reactor for 30minutes at 150 C.Water (3 mL) and ethyl acetate (9 mL) were added the layers were partitioned. Theaqueous layer was extracted with ethyl acetate (2 x 10 mL). The combined organicextracts were washed with saturated sodium chloride (5 mL), dried over MgSO4and concentrated under reduced pressure. The residue was purified by preparativereverse phase HPLC to give 2-(pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazine(14; 0.28 g,60%) as an off white solid: 1H NMR (400 MHz, DMSO-d6) delta 12.24 (s, 1H), 9.00(s, 1H), 8.69 (dd, J = 4.5, 1.6 Hz, 2H), 8.12 (dd, J = 4.5, 1.6Hz, 2H), 7.98 (d, J = 3.6 Hz, 1H), 6.74 (d, J = 3.6 Hz, 1H); ESMSm/z 197.1 (M+1).

The synthetic route of 875781-43-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Burdick, Daniel J.; Wang, Shumei; Heise, Christopher; Pan, Borlan; Drummond, Jake; Yin, Jianping; Goeser, Lauren; Magnuson, Steven; Blaney, Jeff; Moffat, John; Wang, Weiru; Chen, Huifen; Bioorganic and Medicinal Chemistry Letters; vol. 25; 21; (2015); p. 4728 – 4732;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, belongs to pyrazines compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 875781-43-4, Computed Properties of C6H4BrN3

2.1 1.66 g (2.37 mmol) of bis(triphenylphosphine)palladium dichloride and 16.8 g (80 mmol) of 1-methyl-1H-pyrazole-4-boronic acid pinacol ester are added successively to a solution, kept under nitrogen, of 9.4 g (47.0 mmol) of 2-bromo-5H-pyrrolo[2,3-b]pyrazine (prepared in two steps from 3,5-dibromopyrazin-2-amine in accordance with WO2006/15124 or WO2010/68483) in 400 ml of dioxane, and the mixture is stirred at room temperature for 5 minutes. 94 ml of a 2 M aqueous sodium carbonate solution are then added. The mixture is heated to 90 C. and kept at this temperature for 2 hours. The reaction mixture is cooled to room temperature and partitioned between water and ethyl acetate. The combined organic phases are dried over sodium sulfate and evaporated. The residue is boiled in tert-butyl methyl ether, cooled and filtered off with suction. The residue is dried in vacuo: 2-(1-methyl-11H-pyrazol-4-yl)-5H-pyrrolo[2,3-b]pyrazine as orange crystals; HPLC/MS: 1.30 min, [M+H] 200.

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.

Reference:
Patent; MERCK PATENT GMBH; Dorsch, Dieter; Wucherer-Plietker, Margarita; Mueller, Thomas J.J.; Merkul, Eugen; US2013/217951; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 875781-43-4, A common heterocyclic compound, 875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, molecular formula is C6H4BrN3, 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.

2-Bromo-5H-pyrrolo[2,3-b]pyrazine SM-1 (500 mg, 2.5 mmol), 1-Boc-4-(methylamino)piperidine SM-5a (1.082 g, 5.0 mmol), Pd2(dba)3 (139 mg, 0.1 mmol), DavePhos (238 mg, 0.6 mmol) and LiHMDS (12.625 mL, 12 mmol) are taken-up in dry THF (10 mL) and the resulting mixture is flushed with Argon and stirred for 1 h at 80 C. The reaction mixture is diluted with H2O and AcCN, Isolute is added, the solvent is removed in vacuo and the residue is purified via RP HPLC. The product containing fractions of IM-1a (HPLC-MS method A: tRet.=1.72 min; MS (M+H)+=332) are freeze dried.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; Stadtmueller, Heinz; US2013/29993; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, belongs to pyrazines compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. category: Pyrazines

2-bromo-5H- pyrrolo [2,3-b] pyrazine (5.0g, 25.2 mmol) of 1,4-dioxane (100mL) 2.0M NaOH aqueous solution to the partial suspension in (25mL, 50 2.0 mmol) and 37% formaldehyde aqueous solution (19mL, 252 mmol) was added. The reaction mixture of this dark homogeneous mixture was stirred overnight at room temperature. The organics were evaporated under reduced pressure. The aqueous layer was neutralized with 1.0 M HCl, and extracted with EtOAc (2x). And the combined organics concentrated to give a solid orange 2.6 g. When allowed to stand, thick brown precipitate formed in the aqueous layer. This precipitate was collected by filtration, and dried. And extracted with the hot brown solid 10% MeOH / EtOAC (3x200mL). The extracts are combined and evaporated to give an additional solid orange 3.05 g. The entire yield, 5.65g (87%) (2-bromo-7-hydroxymethyl-pyrrolo [2,3-b] pyrazin-5-yl)-methanol.

The synthetic route of 875781-43-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F.HOFFMANN-LA ROCHE AG; HENDRICKS, ROBERT THAN; HERMANN, JOHANNES CORNELIUS; KONDRU, RAMA K; LOU, YAN; LYNCH, STEPHEN M; OWENS, TIMOTHY D; SOTH, MICHAEL; (50 pag.)JP5667692; (2015); B2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 875781-43-4, The chemical industry reduces the impact on the environment during synthesis 875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, I believe this compound will play a more active role in future production and life.

A solution of 2-bromo-5H-pyrrolo[2,3-b]pyrazine (5.00 g, 25.2 mmol, Ark Pharm) in DMF (150 mL) was cooled in an ice bath to about 0 C. and then NaH (60% dispersion in mineral oil, 1.21 g, 30.3 mmol) was added. After about 15 min, 4-tert-butylbenzene-1-sulfonyl chloride (6.46 g, 27.8 mmol) was added. The reaction was maintained between about 0-10 C. for about 2 h. Then, the reaction was diluted with water (200 mL) to give a yellow suspension. The solid was collected by vacuum filtration, while washing with additional water (100 mL), and dried in a vacuum oven at about 70 C. to give 2-bromo-5-(4-tert-butylphenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazine (9.05 g, 91%): LC/MS (Table 2, Method a) Rt=3.05 min; MS m/z: 394/396 (M+H)+.

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, 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBOTT LABORATORIES; US2009/312338; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 875781-43-4,Some common heterocyclic compound, 875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, molecular formula is C6H4BrN3, 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.

[0358] Step 1. To a suspension of 15A (1.0 equiv.) in THF (0.15 M) is added a solution of 2.0 M aqueous NaOH (3 equiv.). The homogeneous reaction mixture is stirred overnight, and then the organics are removed under reduced pressure. The aqueous residue is brought to pH–4 with 1.0 M aqueous HC1. The resulting precipitate is collected by filtration and rinsed with H20 to afford a solid of 1 5B. The filtrate is extracted with EtOAc (2x), and the organics are concentrated under reduced pressure to provide an additional portion of 15B.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, its application will become more common.

Reference:
Patent; TP THERAPEUTICS, INC.; CUI, Jingrong Jean; LI, Yishan; ROGERS, Evan W.; ZHAI, Dayong; WO2015/112806; (2015); A3;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, A new synthetic method of this compound is introduced below., Recommanded Product: 875781-43-4

General procedure: 2-Bromo-5H-pyrrolo[3,2-b]pyrazine(4; 0.471 g,2.39 mmol), 4-pyridylboronic acid (0.58 g, 4.72 mmol), dichloro 1,1′-bis(diphenylphosphino)ferrocenepalladium (II) dichloromethane adduct (0.097 g, 0.12 mmol), acetonitrile(3 mL) and 1M sodium carbonate (3 mL) were placed in a 10 mL CEM microwavevial. The vial was capped and irradiated in a CEM microwave reactor for 30minutes at 150 C.Water (3 mL) and ethyl acetate (9 mL) were added the layers were partitioned. Theaqueous layer was extracted with ethyl acetate (2 x 10 mL). The combined organicextracts were washed with saturated sodium chloride (5 mL), dried over MgSO4and concentrated under reduced pressure. The residue was purified by preparativereverse phase HPLC to give 2-(pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazine(14; 0.28 g,60%) as an off white solid: 1H NMR (400 MHz, DMSO-d6) delta 12.24 (s, 1H), 9.00(s, 1H), 8.69 (dd, J = 4.5, 1.6 Hz, 2H), 8.12 (dd, J = 4.5, 1.6Hz, 2H), 7.98 (d, J = 3.6 Hz, 1H), 6.74 (d, J = 3.6 Hz, 1H); ESMSm/z 197.1 (M+1).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Burdick, Daniel J.; Wang, Shumei; Heise, Christopher; Pan, Borlan; Drummond, Jake; Yin, Jianping; Goeser, Lauren; Magnuson, Steven; Blaney, Jeff; Moffat, John; Wang, Weiru; Chen, Huifen; Bioorganic and Medicinal Chemistry Letters; vol. 25; 21; (2015); p. 4728 – 4732;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 875781-43-4, 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. 875781-43-4 name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, This 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.

The compound prepared in Example 1 (1.26 mg, 0.3 mm), 5-bromo-1 H-pyrrolo [2,3-b] pyrazine (5 9 (63 mg ‘0.006m m o 1), C u I (1 8 mg, 0.09 mm omicron 1), m m L Epsilon13 Nu and 5 m LD Mu F The reaction was stirred at 80 C for 8 hours under inert atmosphere. The end of the reaction was extracted with ethyl acetate and water. The combined organic layers were washed with a saturated NaC1 solution and dried over anhydrous N ^ SOi. Concentrated under reduced pressure, and the residue was purified on a silica gel column to give the compound as an off-white solid. & Lt; 1 & gt; H NMR (500 MHz, CDC13) delta: 8_91 Page 27 of 53

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, and friends who are interested can also refer to it.

Reference:
Patent; NANJING SHENGHE PHARMACEUTICAL CO., LTD.; WANG, YONG; ZHAO, LIWEN; LIU, YANG; ZHANG, JINGZHONG; WANG, DEZHONG; GAO, YIPING; CHEN, HONGYAN; ZHANG, CANG; ZHANG, DI; (68 pag.)TWI523856; (2016); B;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 875781-43-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

Method BSteplIn a dry round-bottomed flask, 2-bromo-5H-pyrrolo[2,3-b]pyrazine (5.0 g, 25.2 mmol) was dissolved in DMF (50 mL). The reaction mixture was cooled to 0C and sodium hydride (60% dispersion in mineral oil, 1.22 g, 30.6 mmol). The reaction mixture was warmed to room temperature and stirred for 15 min then cooled back to 0C and SEM-C1 (5.4 mL, 30.4 mmol) was slowly added. After the addition was complete, the ice bath was removed and the reaction mixture was stirred at room temperature for 1.5 h. The reaction mixture was quenched with 50 mL water and extracted with 150 mL diethyl ether (2x). The combined organic layers were washed twice with 30 mL water and once with 30 mL brine then dried over sodium sulfate, filtered and concentrated. The residue was absorbed on -20 g Si02 and chromatographed over 200g Si02 with EtOAc/Hexanes (gradient: 0-15% EtOAc). All fractions containing product were combined and concentrated to afford 6.61 g (80%) of 2- bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine as a pale yellow oil which gradually solidified.

The synthetic route of 2-Bromo-5H-pyrrolo[2,3-b]pyrazine has been constantly updated, and we look forward to future research findings.

Related Products of 875781-43-4, 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 875781-43-4 as follows.

2-bromo-5H-pyrrolo [2,3-b] pyrazine (10 g, 50.5 mmol)Of tetrahydrofuran (150 mL)Was added sodium hydride (60%, 3.1 g, 78 mmol)The mixture was stirred at room temperature for 1 hour,P-toluenesulfonyl chloride (12.6 g, 65.4 mmol) was added under ice-Continue to stir at room temperature,Diluted with water (100 mL)Dichloromethane extraction (100 mL x 3),Dried over anhydrous sodium sulfate,Concentrated column chromatography (petroleum ether / ethyl acetate (v / v) = 8/1)To give 14.1 g of a pale yellow flocculent solid in a yield of 79.3%.

According to the analysis of related databases, 875781-43-4, the application of this compound in the production field has become more and more popular.