Category: 13526-66-4

Some common heterocyclic compound, 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, molecular formula is C6H3BrClN3, 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. 13526-66-4

Example 70(?)-2-(1-(3-((1 -Methyl-1 H-indazol-5-yl)methyl)imidazo[1 ,2-b]pyridazin-6-yl)ethylidene) hydrazinecarboxamide(6-Chloroimidazo[1 ,2-b]pyridazin-3-yl)(1 -methyl-1 H-indazol-5-yl)methanol (70.1)To a solution of 3-bromo-6-chloroimidazo[1 ,2-b]pyridazine (232.0 mg, 1.00 mmol) in 5 ml_ THF, was added ethylmagnesium bromide (1.50 ml_, 1.50 mmol) at -10 0C. After stirring at – 10 0C for 1 hour, 1 -methyl-1 H-indazole-5-carbaldehyde (240.0 mg, 1.50 mmol) was added. The mixture was allowed to warm to room temperature slowly and stirred for additional 2 hours. The reaction was quenched with Sat. NH4CI solution and concentrated under reduced pressure. The residue was diluted with water, and extracted with EtOAc twice. The organic layers were combined, dried over Na2SO4 and concentrated. The crude product was washed with DCM to give the title compound as a white solid (230 mg, 70 %). 1H-NMR (400MHz, DMSO-Cf6) delta ppm 8.21 (d, 1 H), 8.02 (s, 1 H), 7.81 (s, 1 H), 7.59 (d, 1 H), 7.56 (s, 1 H), 7.49 (d, 1 H), 7.35 (d, 1 H), 6.29 (d, 1 H), 6.21 (d, 1 H), 4.02 (s, 3H). LCMS (method A): [MH]+ = 314, tR = 4.44 min

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 13526-66-4, its application will become more common.

Reference:
Patent; NOVARTIS AG; FU, Xingnian; HE, Feng; LI, Yue; LIU, Lei; MI, Yuan; XU, Yao-chang; XUN, Guoliang; YU, Zhengtian; ZHANG, Ji Yue (Jeff); DAI, Miao; WO2011/18454; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

13526-66-4, Adding a certain compound to certain chemical reactions, such as: 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, belongs to chlorides-buliding-blocks 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 13526-66-4.

[00359] EX. 8-29 free base and hydrochloride salt were prepared in 50 g scale according the following procedures. D [00360] To a solution of 3-bromo-6-chloroinnidazo[1 ,2-b]pyridazine (150 g, 0.65 mol) and 3-(trifluoromethyl)phenylboronic(143 g, 0.65 mol) in dioxane/H2O(2.5 L: 4:1 ) was added K2CO3 (180 g, 1 .3 mol) and Pd(PPh3)4 (10 g, 10 mmol). The mixture was stirred at 80 C for 24 h. The solution was concentrated, partitioned with EA/H2O. The aqueous layer was extracted with EA (500ml_) for 3 times. The collected organic layers was dried over Na2SO , concentrated and purified by column chromatograph (PE:EA, 3:1 to 2:1 ) to give 6-chloro-3-(3-(trifluoromethyl)phenyl)imidazo[1 ,2-b]pyridazine (135.15 g, 70.3%) as yellow solid.

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, 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TOLERO PHARMACEUTICALS, INC.; XU, Yong; BRENNING, Benjamin, Gary; KULTGEN, Steven, G.; LIU, Xiaohui; SAUNDERS, Michael; HO, Koc-Kan; WO2013/13188; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, I believe this compound will play a more active role in future production and life. 13526-66-4

75. 2-(trans-4-((3-(3-fluorophenyl)imidazof1,2-blpyridazin-6- yl)amino)cvclohexyl)propan-2-ol (EX. 8-75) [00463] To a solution of 3-bromo-6-chloroinnidazo[1 ,2-b]pyridazine (500 mg, 2.15 mmol) in a mixed solvent of dioxane (5 ml_) and water (0.5 ml_) was added (3-fluorophenyl)boronic acid (273 mg, 1 .96 mmol), K2CO3 (81 1 mg, 5.88 mmol) and Pd(dppf)2Cl2 (79 mg, 0.098 mmol). The reaction mixture was stirred at 80C overnight under N2. TLC (PE: EA = 5:1 ) showed the starting material was consumed. The mixture was cooled and concentrated. The residue was purified by column chromatography on silica gel (petroleum ether/EtOAc = 20:1 to 1 :1 ) to give 6-chloro-3-(3-fluorophenyl)imidazo[1 ,2-b]pyridazine (300 mg, 56%) as a yellow solid.

The chemical industry reduces the impact on the environment during synthesis 13526-66-4. I believe this compound will play a more active role in future production and life.

Reference:
Patent; TOLERO PHARMACEUTICALS, INC.; XU, Yong; BRENNING, Benjamin, Gary; KULTGEN, Steven, G.; LIU, Xiaohui; SAUNDERS, Michael; HO, Koc-Kan; WO2013/13188; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

13526-66-4, 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. 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, This compound has unique chemical properties. The synthetic route is as follows.

a) S-Bromo-e-il-methyl-piperidin^-yloxyJ-imidazotl^-i lpyridazine To a suspension of NaH (60% in oil, 0.17 g, 4.31 mmol) in dry THF (5 mL) at 0 C was added a solution of 4-hydroxy-/V-methyl piperidine (0.50 g, 4.31 mmol) in dry THF (5 mL). The reaction mixture was stirred a 0C for 5 min then at RT for 15 min. The reaction mixture was cooled back to 0C and a solution of 3-bromo-6-chloroimidazo[1 ,2- ?>]pyridazine (0.50 g, 2.15 mmol) in dry THF (10 mL) was added dropwise. The reaction mixture was then allowed to warm up slowly to RT and stirred for 4 h. The reaction mixture was quenched by addition of water (10 mL), diluted with EtOAc (100 mL) and washed with water (2 x 50 mL). The organic layer was dried and concentrated in vacuo. Purification by column chromatography (EtOAc-2M NH3 in MeOH 5-100%) gave a solid (0.35 g, 53%); 1H NMR (400 MHz, DMSO-d6) delta ppm 8.04 (d, J=9.6 Hz, 1 H), 7.73 (s, 1H), 6.93 (d, J=9.6 Hz, 1 H), 4.99 (m, 1 H), 2.75-2.56 (m, 2H), 2.27-2.13 (m, 5H), 2.13-2.01 (m, 2H), 1.90-1.65 (m, 2H); m/z (ES+APCI)+: 311/313 [M+H]+.

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; MEDICAL RESEARCH COUNCIL TECHNOLOGY; OSBORNE, Simon; CHAPMAN, Timothy; LARGE, Jonathan; BOULOC, Nathalie; WALLACE, Claire; WO2011/101640; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

13526-66-4, 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. 13526-66-4 name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, 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.

Intermediate Q6-Chloro-3-(3-chlorophenyl)imidazo[1,2-b]pyridazine A mixture of 4.18 g (18 mmol) of 3-bromo-6-chloroimidazo[1,2-b]pyridazine, 2.95 g (18.9 mmol) of 3-chlorophenylbronic acid, 0.83 g (0.72 mmol) of tetrakis(triphenylphosphine)palladium (0) and 32.3 ml of 2 M aqueous sodium carbonate solution are heated to boiling under in 188 ml of 1,4-dioxane for 12 h.The reaction mixture obtained in this way is mixed with sat. aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phase is washed with sat. aqueous sodium chloride solution and dried over sodium sulfate, and the solvent is evaporated off. In the final purification by chromatography on silica gel, 3.46 g (73%) of the desired product were isolated.1H-NMR (DMSO-D6): delta=7.43 (d, 1H); 7.44 (dd, 1H); 7.53 (t, 1H); 8.05 (dt, 1H); 8.16 (t, 1H); 8.29 (d, 1H); 8.38 (s, 1H) ppm.MS (ESI+): m/z=264 [M+H]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, and friends who are interested can also refer to it.

Reference:
Patent; PRIEN, Olaf; Eis, Knut; Bader, Benjamin; Guenther, Judith; Von Bonin, Arne; US2009/93475; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

13526-66-4, 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. 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, A new synthetic method of this compound is introduced below.

13.9 g (59.8 mmol) 3-bromo-6-chloro-imidazo[1 ,2-b]pyridazine were suspended in 508 mL 1 ,4-dioxane. 10.1 g (62.8 mmol) 2-benzofuranylboronic acid, 2.76 g (2.29 mmol) tetrakis(tn’phenylphosphino)palladium-(0) and 19.0 g (179 mmol) sodium carbonate were added. The obtained mixture was heated to 100C for 24 h.400 mL of a saturated aqueous ammonium chloride solution were added. The obtained mixture was extracted with ethyl acetate. The combined organic layers were washed with brine and dried over magnesium sulfate. After evaporation of the solvent, the obtained solid material was digested in 40 mL of a mixture of dichloromethane and methanol (8:2), filtered off and dried in vacuo to yield 5.42 g (44%) of the title compound as solid material.1H-NMR (300 MHz, DMSO-d6): delta [ppm]= 7.23 – 7.40 (m, 2H), 7.51 (d, 1 H), 7.59 – 7.67 (m, 2H), 7.77 (d, 1 H), 8.33 – 8.40 (m, 2H).LCMS (Method 1 ): Rt = 1.35 min; MS (ESIpos) m/z = 270 [M+H]+.

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; Bayer Intellectual Property GmbH; EIS, Knut; PUeHLER, Florian; ZORN, Ludwig; SCHOLZ, Arne; LIENAU, Philip; GNOTH, Mark, Jean; BOeMER, Ulf; GUeNTHER, Judith; FANGHAeNEL, Joerg; KORR, Daniel; WO2012/175591; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

13526-66-4, 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. 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution under N2 of3-bromo-6-chloro-imidazo[1,2-b]pyridazine (1 g, 4.3 mmol) in dioxane (45 mL), Pd[P(C6H5)3]4(0.248 g, 0.2 mmol), 5-indole-5-boronic acid (0.728 g, 4.51 mmol) and Na2CO3(2 M, 7.7 mL) were added. The mixture was stirred for 21 h at 100 C. Thereaction was monitored by TLC. The solvent was evaporated under reducedpressure. The crude residue was diluted and stirred in AcOEt and ammoniumchloride solution (saturated). The product was extracted with AcOEt, and theorganic layer was washed with NaCl solution. The organic layer was dried overNa2SO4, filtered, and evaporated under reduced pressure.The crude residue was purified by chromatography on silica gel using DCM-AcOEt(6:4) afforded 6a in 72% yield(0.840 g) as a light green powder.

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:
Article; Bendjeddou, Lyamin Z.; Loaec, Nadege; Villiers, Benoit; Prina, Eric; Spaeth, Gerald F.; Galons, Herve; Meijer, Laurent; Oumata, Nassima; European Journal of Medicinal Chemistry; vol. 125; (2017); p. 696 – 709;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 13526-66-4 name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, 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. 13526-66-4

To a solution of 3-bromo-6-chloroimidazo[1 ,2-b]pyridazine (232.0 mg, 1 .00 mmol) in THF (5 ml_) was added EtMaBr (1 M in THF, 1 .50 ml_, 1 .50 mmol) at -10 QC. After stirring at -10 QC for 1 h, i -methyl-I H-indazole-5-carbaldehyde (240.0 mg, 1.50 mmol) was added. The mixture was allowed to warm to rt slowly and stirred for 2 h. The reaction was quenched with saturated NH4CI solution and concentrated under reduced pressure. The residue was diluted with water and extracted with EtOAc twice. The organic layers were combined, dried over Na2SO4 and concentrated. The crude product was washed with DCM to give the title compound as a white solid (230 mg, 70 %). 1H-NMR (400MHz, DMSO-Cf6) delta ppm 8.21 (d, 1 H), 8.02 (s, 1 H), 7.81 (s, 1 H), 7.59 (d, 1 H), 7.56 (s, 1 H), 7.49 (d, 1 H), 7.35 (d, 1 H), 6.29 (d, 1 H), 6.21 (d, 1 H), 4.02 (s, 3H). LCMS (method A): [MH]+ = 314, tR = 4.44 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; DAI, Miao; FU, Xingnian; HE, Feng; JIANG, Lei; LI, Yue; LIANG, Fang; LIU, Lei; MI, Yuan; XU, Yao-chang; XUN, Guoliang; YAN, Xiaoxia; YU, Zhengtian; ZHANG, Ji, Yue; WO2011/20861; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

13526-66-4, Adding some certain compound to certain chemical reactions, such as: 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, 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 13526-66-4.

13.9 g (59.8 mmol) 3-bromo-6-chloro-imidazo[1 ,2-b]pyridazine were suspended in 508 mL 1 ,4-dioxane. 10.1 g (62.8 mmol) 2-benzofuranylboronic acid, 2.76 g (2.29 mmol) tetrakis(triphenylphosphino)palladium-(0) and 19.0 g (179 mmol) sodium carbonate were added. The obtained mixture was heated to 100C for 24 h. 400 mL of a saturated aqueous ammonium chloride solution were added. The obtained mixture was extracted with ethyl acetate. The combined organic layers were washed with brine and dried over magnesium sulfate. After evaporation of the solvent, the obtained solid material was digested in 40 mL of a mixture of dichloromethane and methanol (8:2), filtered off and dried in vacuo to yield 5.42 g (44%) of the title compound as solid material. 1H-NMR (300 MHz, DMSO-d6): delta [ppm]= 7.23 – 7.40 (m, 2H), 7.51 (d, 1 H), 7.59 – 7.67 (m, 2H), 7.77 (d, 1 H), 8.33 – 8.40 (m, 2H). LCMS (Method 1 ): Rt = 1 .35 min; MS (ESIpos) m/z = 270 [M+H]+.

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 13526-66-4.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ZORN, Ludwig; EIS, Knut; SCHULZE, Volker; SUeLZLE, Detlev; PUeHLER, Florian; LIENAU, Philip; BOeMER, Ulf; PETERSEN, Kirstin; HAeGEBARTH, Andrea; WO2014/118135; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, molecular formula is C6H3BrClN3, 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. 13526-66-4

13.9 g (59.8 mmol) 3-bromo-6-chloro-imidazo[l,2-b]pyridazine were suspended in 508 mL 1,4-dioxane. 10.1 g (62.8 mmol) 2-benzofuranylboronic acid, 2.76 g (2.29 mmol) tetrakis(triphenylphosphino)palladium-(0) and 19.0 g (179 mmol) sodium carbonate were added. The obtained mixture was heated to 100C for 24 h. 400 mL of a saturated aqueous ammonium chloride solution were added. The obtained mixture was extracted with ethyl acetate. The combined organic layers were washed with brine and dried over magnesium sulfate. After evaporation of the solvent, the obtained solid material was digested in 40 mL of a mixture of dichloromethane and methanol (8:2), filtered off and dried in vacuo to yield 5.42 g (44%) of the title compound as solid material. ^-NMR (300M HZ, DMSO-d6): delta [ppm] = 7.23 – 7.40 (2H), 7.51 (1H), 7.59 – 7.67 (2H), 7.77 (1H ), 8.33 – 8.40 (2H).LCMS (Method 1) : Rt= 1.35 min; MS (ESIpos) m/z = 270 [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 13526-66-4, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; PUeHLER, Florian; ZORN, Ludwig; SCHULZE, Volker; SUeLZLE, Detlev; LIENAU, Philip; WENGNER, Antje, Margret; PETERSEN, Kirstin; BOeMER, Ulf; WO2014/128093; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics