Category: 13526-66-4

Electric Literature of 13526-66-4, 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 13526-66-4 as follows.

Example 1 (£)-2-(1-(3-((7-Fluoroquinolin-6-yl)methyl)imidazo[1 ,2-b]pyridazin-6-yl)ethylidene)- hydrazinecarboxamide6-Chloro-imidazo[1 ,2-b]pyridazin-3-yl)-(7-f luoro-quinolin-6-yl)-methanol (1.1 ) To a solution of 3-bromo-6-chloro-imidazo[1 ,2-b]pyridazine (13.27 g, 57.1 mmol) in 160 ml of THF was added EtMgBr (68.5 ml, 68.5 mmol) solution at room temperature. The reaction mixture was stirred for 30 min and a suspension of 7-Fluoro-quinoline-6-carbaldehyde (10 g, 57.1 mmol) in 40 ml of THF was added. The resulting mixture was stirred at roomtemperature for 3 hrs and quenched with 400 ml of water. After stirring for additional 1 hr, the precipitate was collected by filtration, washed with EtOAc and dried over vacuum oven overnight to afford 13 g (yield: 69%) of title compound. 1H-NMR (400MHz, DMSO-Cf6) delta ppm 8.91 (dd, 1 H), 8.49 (d, 1 H), 8.28 (d, 1 H), 8.24 (d, 1 H), 7.74 (d, 1 H), 7.54(q, 1 H), 7.51 (s, 1 H), 7.40 (d, 1 H), 6.54 (m, 2H).

According to the analysis of related databases, 13526-66-4, the application of this compound in the production field has become more and more popular.

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

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, Safety of 3-Bromo-6-chloroimidazo[1,2-b]pyridazine

General procedure: Example 15-5 General procedure for the synthesis of 3-bromo-6-R1-imidazo[1,2-b]pyridazine 4*. (R1= aminyl) by amine (R1H) displacement A mixture of 3-bromo-6-chloroimadazo[1,2-b]pyridazine 2*a (15 g, 64.52 mmol, 1 eq.), the appropriate amine (R1H, 96.78 mmol, 1.5 eq.) and DIPEA (16.90 ml, 96.78 mmol, 1.5eq.) in ethanol (15 ml) was placed in the CEM Microwave and stirred and heated at 160 C for 10 minutes and 180 C for 2 hours. The solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate, washed with water (twice) and brine and then filtered through a pad of silica and washed with ethyl acetate. The organic solvent was evaporated under reduced pressure and the crude residue was slurried in hexane/10% ether. The crystalline product was filtered and washed with hexane/ 10% ether and dried to give the intermediate 3-bromo-6-R1-imidazo[1,2-b]pyridazine 4*.

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; Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.; Ullrich, Axel; Falcenberg, Mathias; EP2818471; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 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.

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 (300MHz, 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 chemical industry reduces the impact on the environment during synthesis 3-Bromo-6-chloroimidazo[1,2-b]pyridazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; EIS, Knut; PUeHLER, Florian; ZORN, Ludwig; SCHOLZ, Arne; LIENAU, Philip; GNOTH, Mark, Jean; BOeMER, Ulf; GUeNTHER, Judith; WO2013/41634; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Computed Properties of C6H3BrClN3

3-Bromo-6-chloro-imidazo[1,2-b]pyridazine (CAS 13526-66-4, 1.327 g, 5.71 mmol) was dissolved THF (40 mL) and under nitrogen conditions, it was cooled down to 0 0C and ethyl magnesium bromide solution (1 M, 6.85 mL) was added. The RM was stirred at RT for 30 min then a solution of 7-fluoro-quinoline-6-carbaldehyde (Intermediate K, 1.0 g, 5.71 mmol) in THF (20 mL) was added by 0 0C. The RM was stirred at RT for 2 h. The solvent was partially removed by evaporation and water (40 mL) was added to the residual mash. After 1 h stirring, the crystallized product was filtered and dried overnight under vacuum to afford the title compound as a powder (tR 3.70 min (conditions 5), MH+ = 329, 1H-NMR in DMSO-d6: 8.90 (dd, 1H); 8.46 (d, 1H); 8.29 – 8.23 (m, 2H); 7.72 (d, 1H); 7.54 – 7.49 (m, 2H); 7.40 (d, 1 H); 6.56 – 6.49 (m, 2H)).

The synthetic route of 13526-66-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; McCARTHY, Clive; SCHOEPFER, Joseph; STUTZ, Stefan; WO2011/15652; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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., Formula: C6H3BrClN3

Intermediate P3-Bromo-6-(3-chlorophenoxy)imidazo[1,2-b]pyridazineVariant 3: 5 g (21.5 mmol) of 3-bromo-6-chloroimidazo[1,2-b]pyridazine, 3 g (23.7 mmol) of 3-chlorophenyl, 246 mg (0.27 mmol) of tris(dibenzylidineacetone)dipalladium, 500 mg of rac-BINAP and 4.1 g of sodium tert-butoxide are stirred in a mixture of 100 ml of dimethylformamide and 200 ml of tetrahydrofuran at 100 C. under a protective gas atmosphere for 12 h.The reaction mixture is then mixed with saturated sodium chloride solution. The aqueous phase is extracted with ethyl acetate. The organic phase is washed twice with dilute aqueous NaCl solution and once with saturated aqueous NaCl solution and dried over sodium sulfate. In the final purification by chromatography on silica gel, 2.78 g (40%) of the desired product were isolated.1H-NMR (DMSO-D6): delta=7.22 (d, 1H); 7.31-7.42 (m, 2H); 7.51 (d, 1H); 7.55 (t, 1H); 7.83 (s, 1H); 8.25 (d, 1H) ppm.MS (ESI): m/z=324/326 [M+H]+

According to the analysis of related databases, 13526-66-4, the application of this compound in the production field has become more and more popular.

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

Reference of 13526-66-4, 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. 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Under an argon atmosphere, 3-Bromo-6-chloroimidazo [1,2-b] pyridazine (721 mg, 3.10 mmol)Of 1,4-dioxane (25 mL),Water (5 mL)Was added 2,2,2-trifluoro-1- (4- (2-fluoro-4- (4,4,5,5-tetramethyl- 1, 3,2-dioxaborolan-2-yl) Phenyl) piperazin-1-yl) ethanone (1.50 g, 3.72 mmol),Sodium carbonate (1.15 g, 10.9 mmol),Tetrakis triphenylphosphine palladium (143 mg, 0.124 mmol) was added and degassed,Substitution with argon.Followed by stirring at 100 C. for 17 hours.After completion of the reaction,The reaction solution was made basic by adding 1 N sodium hydroxide solution,And extracted with chloroform.The organic layer was dried over anhydrous magnesium sulfate,The solvent was distilled off,And dried to give the title compound (788 mg, 77%).

The synthetic route of 3-Bromo-6-chloroimidazo[1,2-b]pyridazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YAKULT HONSHA COMPANY LIMITED; ABE, ATSUHIRO; MAE, MASAYUKI; YAMAZAKI, RYUTA; SASAI, TOSHIO; NISHIYAMA, HIROYUKI; NAGAOKA, MASATO; MATSUZAKI, TAKESHI; (47 pag.)JP6023630; (2016); B2;,
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Chlorides – an overview | ScienceDirect Topics

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., Recommanded Product: 3-Bromo-6-chloroimidazo[1,2-b]pyridazine

To a solution of 3-bromo-6-chloroimidazo[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 (811 mg, 5.88 mmol) and Pd(dppf)2Cl2 (79 mg, 0.098 mmol). The reaction mixture was stirred at 80 C. 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 synthetic route of 13526-66-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tolero Pharmaceuticals, Inc.; Xu, Yong; Brenning, Benjamin Gary; Kultgen, Steven G.; Liu, Xiaohui; Saunders, Michael; Ho, Koc-Kan; (119 pag.)US9416132; (2016); B2;,
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. Computed Properties of C6H3BrClN3

To a solution of 3-bromo-6-chloro-imidazo[1 ,2-b]pyridazine (2.40 g, 10.35 mmol) in 30 ml_ of THF was added EtMgBr (1 M in THF, 12.43 ml_, 12.42 mmol) solution at rt. The solution was stirred for 30 min and a solution of 5,7-difluoroquinoline-6-carbaldehyde (2.0 g, 10.35 mmol) in 1 O mL of THF was added. The resulting mixture was stirred at rt for additional 2 h and then quenched with 50 ml_ of NH4CI solution. The solution was extracted with EtOAc and the combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated in vacuo to afford 3.48 g (97%) of the title compound. LCMS (method B): [MH]+ = 347, tR = 1 .23 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; 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, These common heterocyclic compound, 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, 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 mixture of 3-bromo-6-chloro-1-yl-imidazo[1,2-b]pyridazine (1.00 g, 4.3 mmol) in 1,2-dimethoxy ethane (1 mL) was added diisopropyl ethyl amine (0.5 mL) and 1-BOC-piperazine (2.41 g, 13 mmol). The mixture was degassed (4 cycles of vacuum and nitrogen) and heated at 120 C. for 27 hours. The reaction mixture was cooled to room temperature, treated with saturated aqueous sodium bicarbonate (100 mL) and extracted with ethyl acetate (2¡Á100 mL). The organic layers were combined and dried with magnesium sulfate, filtered and evaporated to a residue, which was purified by chromatography on silica gel; elution with a gradient of hexane/ethyl acetate gave 4-(3-bromo-imidazo[1,2-b]pyridazine-6-yl)-piperazine-1-carboxylic acid tert-butyl ester as an off-white solid (1.01 g, 83%): mp 176-9 C.; LC/MS [M+H]+ 382, 384.

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; ALCON MANUFACTURING, LTD.; US2008/153813; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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., 13526-66-4

mixture of 2.0 g (16.8 mmol) furo[3,2-b]pyridine and anhydrous THF (100 mL) was cooled to -78 C. 10.1 mL (25.2 mmol) of a 1 .6 M solution of n-butyllithium in hexane was added and the resulting mixture stirred for 1 h at -78 C. 6.8 mL (25.2 mmol) of tributyltin chloride was added at -78 C. The cooling bath was removed and the reaction was stirred at room temperature over night. Methanol was carefully added and the solvent evaporated. The obtained residue was purified by flash chromatography to yield 7.4 g of crude product of the corresponding 2-stannylbenzofurane, which was used without further purification. In an inert atmosphere, 3.0 g (12.9 mmol) of 3-bromo-6-chloro-imidazo[1 ,2-b]- pyridazine, 6.85 g (16.8 mmol) of the crude 2-stannylfuro[3,2-b]pyridine, 246 mg (1 .29 mmol) copper (I) iodide and 453 mg (0.645 mmol) bis(triphenylphosphine) palladium(ll)chloride in 100 mL of THF was stirred over night at 85 C in a sealed pressure tube. The solvent was evaporated, the obtained solid was digested in dichloromethane/methanol and filtered off. The solid was washed with methanol and hexane to give 2 g of the title compound as solid material. 1H-NMR (300 MHz, DMSO-de), delta [ppm]= 7.35-7.45 (1 H), 7.57-7.64 (1 H), 7.65-7.70 (1 H), 8.08-8.15 (1 H), 8.40-8.47 (1 H), 8.47-8.52 (1 H), 8.54-8.62 (1 H). LCMS (Method 3): Rt = 0.91 min; MS (ESIpos) m/z = 271 [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; 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