Category: 875781-43-4

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. SDS of cas: 875781-43-4

To a stirred solution of2-bromo-5H-pyrrolo[2,3-b]pyrazine (1.0 g,5.05 mmol)inTHF (10 mL)at 0 oc was added NaH (225 mg,5.63 mmol,60%)and the mixture was stirred for30 min. Benzenesulfonyl chloride (0.72 mL,5.66 mmol)was added dropwise and the mixturestirred at room temperature for an additional2 h. The mixture was quenched with sat. aq. NH4Cl15 (30 mL)and extracted with EtOAc (30 mL x 2). The combined organic layers were dried overanhydrous Na2S04,filtered and concentrated in vacuo to give the title compound (1.4 g,82%)as a yellow solid that required no further purification. 1H NMR (400 MHz,CD30D)8 8.45 (s,1H),8.24 (d,J = 4.0 Hz,1H),8.20- 8.15 (m,2H),7.74- 7.67 (m,1H),7.64- 7.59 (m,2H),6.85 (d,J= 4.0 Hz,1H).

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

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; CYR, Patrick; BRONNER, Sarah; ROMERO, F. Anthony; MAGNUSON, Steven; TSUI, Vickie Hsiao-Wei; WAI, John; LAI, Kwong Wah; WANG, Fei; (251 pag.)WO2017/205536; (2017); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 875781-43-4, 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. 875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, This compound has unique chemical properties. The synthetic route is as follows.

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

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, 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 (300 mg, 1.52 mmol) was dissolved in N, N- dimethylformamide (8 mL)Sodium hydride (60%, 91.3 mg, 2.28 mmol) was added under ice bath and stirring continued at this temperature. After 30 min 2- (trimethylsilyl) ethoxymethyl chloride (404 muL, 2.26 mmol ),Stir at room temperature for 12h. Quenched with water (20 mL)The mixture was extracted with dichloromethane (30 mL × 2) and concentrated for column chromatography (eluent: PE / EtOAc (v / v) = 5/1) to give 270 mg of a yellow oil. Yield: 54.3%.

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; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Liu Bing; Bai Shun; Zhou Youbo; Yang Tiping; He Wei; Zhang Yingjun; Zheng Changchun; (103 pag.)CN106749268; (2017); A;,
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. HPLC of Formula: C6H4BrN3

To a solution of I-69 (300 mg, 0.6 mmol) in DMF (10 mL) are added I-87 (140 mg, 0.7 mmol), tetrakis(triphenylphosphine)palladium (0) (70 mg, 0.06 mmol) and 2M Na2CO3 (1.5 mL, 3.0 mmol). The mixture is heated to 100 C. for 1 hour in a microwave reactor. The mixture is cooled down and is extracted with H2O (20 mL) and EtOAc (30 mL). The combined organic layer is dried with MgSO4 and is filtered. The filtrate is concentrated and the residue is purified by silica gel flash column chromatography with 10% MeOH in CH2Cl2 as the eluent to afford the title compound (200 mg). Example 176-180, Table 1-the reaction is run at 120 C.Example 176-180, Table 1-the reaction is run at 120 C. [0509] Example 184-185, Table 1-the reaction is run at 120 C Example 191, Table 1-the reaction is run at 120 C. Example 239-243, Table 1-the reaction is run for 6 hours at 100 C. in an oil bath

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

Reference:
Patent; Boehringer Ingelheim International GmbH; BYLOCK, Lars Anders; US2013/195879; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature 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.

Step 1To a 500 ml three necked round bottom flask, 2-bromo-5H-pyrrolo[2,3-b]pyrazine (5.0 g,0.0252 mole) was taken in CH2C12 (150 ml). The reaction mixture was cooled to 0 C and diethylaluminiumchloride (1M solution in hexanes) (9.11 g, 0.0756 mole) was added drop wise at the same temperature under nitrogen atmosphere. The reaction mixture was stirred for 30 min at 0 C followed by slow addition of pivoloyl chloride (29.45 g, 0.2444 mole) over 15min at the same temperature. After completion of the addition, the reaction mixture was warmed up to RT Attorney Docket No. 11913-1008 and then up to 40 C and stirred for 16 hrs. The completion of the reaction was monitored on TLC using hexanes: ethyl acetate (5:5) as a mobile phase. After completion of the reaction, the reaction mixture was poured in saturated NaHC03 solution with stirring at 10 C, diluted with CH2C12 and filtered through high flow. The filtrate was collected and washed with brine solution. Layers were separated and the aq. Layer was extracted with CH2C12. The combined organic layer was dried over Na2S04, filtered and concentrated to afford crude product which was subjected for the column purification. The crude compound was purified using column purification by eluting the compound with 10 -25% ethyl acetate in hexanes to yield 5.3g of l-(2- bromo-5H-pyrrolo[2,3-b] pyrazine-7-yl)- 2,2-dimethyl propan-l-one

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; PRINCIPIA BIOPHARMA INC.; GOLDSTEIN, David Michael; BRAMELD, Kenneth Albert; VERNER, Erik; WO2012/158785; (2012); A1;,
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.

In the reactor by adding 5-bromo-1H-pyrrolo [2,3-b] pyrazine (59.4 mg, 0 . 3mmol), step 5 the material 3-ethynyl-4-methyl-N-(4 – ((3-methyl -3,8-diazabicyclo [3.2.1] octane-8-yl) methyl) – 3 – (trifluoromethyl)-phenyl) benzamide (112 mg, 0 . 3mmol), bistriphenyl phosphorus palladium chloride (22 mg, 0 . 03mmol), three ring hexyl phosphine (16 mg, 0 . 06mmol), cuprous iodide (6 mg, 0 . 03mmol), cesium carbonate (99 mg, 0 . 3mmol), 6 drop N, N-diisopropyl ethylamine, for 80 C reaction under 12h. After the reaction, by adding ethyl acetate and ammonia-water extraction, and with a saturated NaCl solution, anhydrous Na 2 SO 4 drying, filtering, turns on lathe does, column chromatography purification to obtain a target compound.

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; 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

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. Recommanded Product: 2-Bromo-5H-pyrrolo[2,3-b]pyrazine

2-bromo-5H-pyrrolo[2,3-b]pyrazine (5 g, 25 mmol) was added to chlorosulfonic acid (20 mL) at 0C. The reaction was heated to 100-120C for 2.5 hours before cooling and pouring into ice-water (80 mL). The solution was extracted into EtOAc (2 x 100 mL), the organic layers combined, washed with brine, dried over sodium sulphate and concentrated in vacuo. The residue was added to a solution of isopropylamine (881 mg, 15 mmol) and triethylamine (2.66 g, 26 mmol) in DCM (60 mL) at 0C. The reaction was stirred at 0C for 3 hours, diluted with water (50 mL) and extracted into EtOAc (2 x 80 mL). The organic layers were combined, washed with brine, dried over sodium sulphate and concen- trated in vacuo. The solid was triturated with TBME to afford the title compound (2 g, 49% over 2 steps) as a brown solid that was used directly in the next step.

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

Reference:
Patent; PFIZER INC.; THORARENSEN, Atli; BROWN, Matthew Frank; CASIMIRO-GARCIA, Agustin; CHE, Ye; FLANAGAN, Mark Edward; GILBERT, Adam Matthew; HAYWARD, Matthew Merrill; TELLIEZ, Jean-Baptiste; UNWALLA, Rayomand Jal; TRUJILLO, John I.; LIANG, Sidney Xi; (212 pag.)WO2016/178110; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – 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. 875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 2-Bromo-5H-pyrrolo[2,3-b]pyrazine

To a solution of 2-bromo-5H-pyrrolo [2, 3-b] pyrazine (1.94 g, 9.8 mmol) in DMF (20 mL) was added sodium hydride (60, 525.3 mg, 13.13 mmol) in an ice bath. The mixture was stirred at this temperature for 30 min and then SEMCl (2.26 mL, 12.6 mmol) was added. The mixture was stirred at rt overnight. The reaction mixture was quenched with water (40 mL) . The resulting mixture was extracted with DCM (30 mL × 3) . The combined organic layers were dried over anhydrous Na2SO4and concentrated in vacuo. The residue was purified by silica gel column chromatography eluted with PE/EtOAc (v/v) 7/1 to give a light yellow oily product (2.40 g, 75.0) .[0819]MS (ESI, pos. ion) m/z: 328.15 [M+1]+.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 875781-43-4.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; LIU, Bing; ZHANG, Yingjun; CHENG, Changchung; HUANG, Jiuzhong; BAI, Shun; REN, Xingye; LI, Zhi; ZHOU, Youbai; (368 pag.)WO2016/615; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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

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).

Statistics shows that 2-Bromo-5H-pyrrolo[2,3-b]pyrazine is playing an increasingly important role. we look forward to future research findings about 875781-43-4.

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

Electric Literature 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.

To a stirred solution of 2-bromo-5H-pyrrolo[2,3-b]pyrazine (from Ark Pharm, cat AK-23813, 1.00 g, 5.05 mmol) in tetrahydrofuran (10 mL), NaH (60% w/w dispersion form in mineral oil, 283 mg, 7.07 mmol) was added at 0 C. After 0.5 hour, benzenesulfonyl chloride (644 muL, 5.05 mmol) was added dropwise. After another 1 hour, the reaction mixture was quenched with saturated aqueous NH4Cl and extracted with methylene chloride. The combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified on silica gel (eluting with 0 to 50% ethyl acetate (EtOAc) in hexanes) to give the desired product (1.50 g, 88%). LCMS calculated for C12H9BrN3O2S (M+H)+: m/z=339.2. Found: 339.2.

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

Reference:
Patent; Incyte Corporation; Lu, Liang; He, Chunhong; Yao, Wenqing; US2014/45814; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem