Category: 13526-66-4

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

a) ierf-Butyl 4-[(3-bromoimidazo[1 ,2-b]pyridazin-6-yl)amino]piperidine-1 -carboxylateA solution of 3-bromo-6-chloroimidazo[1 ,2-b]pyridazine (3.00 g, 12.9 mmol 1.0 eq) in NMP (15 ml_) was treated with te/f-butyl 4-aminopiperidine-1 -carboxylate (5.10 g, 25.8 mmol, 2.0 eq), DIPEA (5.60 mL, 32.3 mmol, 2.5 eq) and heated at 130C for 5 h. The reaction mixture was diluted with DCM (100 mL) and washed with de-ionised water (3 x 150 mL). The separated organic was concentrated in vacuo and column chromatography (10-80% EtOAc/pet ether) gave a brown solid (3.01 g, 59%); 1H NMR (400 MHz, DMSO-d6) delta ppm 7.71 (d, J=9.6 Hz, 1 H), 7.48 (s, 1 H), 7.10 (d, br, J=7.3 Hz, 1H), 6.68 (d, J=10.1 Hz, 1H), 3.87-3.82 (m, 3H), 3.02-2.93 (m, 2H), 2.02-1.98 (m, 2H), 1.41 (s, 9H), 1.40-1.31 (m, 2H); m/z (ES+APCI)+: 396/398 [M+H]+.

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

Reference:
Patent; MEDICAL RESEARCH COUNCIL TECHNOLOGY; OSBORNE, Simon; CHAPMAN, Timothy; WALLACE, Claire; WO2012/127212; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. COA of Formula: C6H3BrClN3

In an inert atmosphere, 3.0 g (12.9 mmol) of 3-bromo-6-chloroimidazo[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 85C 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.

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; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; PUeHLER, Florian; ZORN, Ludwig; SCHULZE, Volker; SUeLZLE, Detlev; LIENAU, Philip; HAeGEBARTH, Andrea; PETERSEN, Kirstin; BOeMER, Ulf; WO2013/149909; (2013); A1;,
Chloride – Wikipedia,
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: 13526-66-4

To a solution of 3-bromo-6-chloro-imidazo[1 ,2-b]pyridazine (13.27 g, 57.1 mmol) in 160 ml_ THF was added EtMgBr (1 M in THF, 68.5 ml_, 68.5 mmol) solution at rt. 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 rt for 3 h and then quenched with 400 ml_ water and stirred for an additional 1 h. The precipitate was collected by filtration, washed with EtOAc and dried over vacuum oven overnight to afford 13 g (69%) of the 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).

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

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

Reference of 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.

Preparation of trans-4-(3-bromoimidazo[1,2-b]pyridazin-6-ylamino)cyclohexanol To 6-chloro-3-bromoimidazo[1,2-b]pyridazine (1.00 g, 4.30 mmol, 1.0 equiv) and p-TSA (818 mg, 4.30 mmol, 1.0 equiv) in DMSO (7.00 mL) was added trans-4-aminocyclohexanol (1.49 g, 12.9 mmol, 3.0 equiv). The mixture was heated at 100 C. for 24 h. Purification by column chromatography using 5% methanol in dichloromethane elution gave 1.1 g of the yellow solid, 83%.

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

Reference:
Patent; Califia Bio, Inc.; GOODFELLOW, VAL S.; NGUYEN, THONG X.; RAVULA, SATHEESH B.; GELBARD, HARRIS A.; US2014/256733; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application 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.

) 3-Bromo-6-{1 -methyl piperidin-4- loxy)imidazo[1 ,2-b]pyridTo a solution of 1-methylpiperidin-4-ol (375 mg, 3.2 mmol, 1.5 eq) in anhydrous THF (15 ml_) was added NaH (60% in mineral oil, 130 mg, 3.2 mmol, 1.5 eq) at 0C. The mixture was allowed to stir at RT for 30 min, then 3-bromo-6-chloro-imidazo[1 ,2-fa]pyridazine (500 mg, 2.14 mmol, 1.0 eq) was added and heated to 65C for 4 h. The mixture was allowed to cool, diluted with EtOAc (100 mL) and washed with water (50 mL). The organic layer was dried (Na2S04), concentrated under reduced pressure and purification by silica gel chromatography (5-10% MeOH/CHCI3) gave a pale yellow solid (100 mg, 15%); H NMR (400 MHz, DMSO-dB) delta ppm 8.04 (d, =10.0 Hz, 1 H), 7.74 (s, 1 H), 6.93 (d, J=9.6 Hz, 1 H), 5.04-5.00 (m, 1 H), 2.75-2.65 (m, 2H), 2.32-2.24 (m, 5H), 2.15-2.05 (m, 2H), 1.85-1.75 (m, 2H); m/z (APCIf: 311/313 [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, 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MEDICAL RESEARCH COUNCIL TECHNOLOGY; OSBORNE, Simon; CHAPMAN, Timothy; WALLACE, Claire; WO2012/127212; (2012); 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. Safety of 3-Bromo-6-chloroimidazo[1,2-b]pyridazine

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 90 mL (180 mmol) of a 2M aqueous sodium carbonate solution 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 (2H), 7.51 (1 H), 7.59 – 7.67 (2H), 7.77 (1 H), 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 INTELLECTUAL PROPERTY GMBH; EIS, Knut; PUeHLER, Florian; ZORN, Ludwig; SCHULZE, Volker; SUeLZLE, Detlev; LIENAU, Philip; HAeGEBARTH, Andrea; PETERSEN, Kirstin; BOeMER, Ulf; WO2013/144189; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 13526-66-4, 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.

PREPARATION 9; 3-(3-Methoxypyridazin-4-yl)-N-[(1S)-1-phenylethyl]imidazo[1,2-b]pyridazin-6-amine a) 6-Chloro-3-(3-methoxypyridazin-4-yl)imidazo[1,2-b]pyridazine A mixture of 3-bromo-6-chloroimidazo[1,2-b]pyridazine (preparation 1b, 182 mg, 0.78 mmol), 3-methoxy-4-(tributylstannyl)pyridazine (preparation 8b, 313 mg, 0.78 mmol), copper (I) iodide (15 mg, 0.08 mmol) and dry N,N’-dimethylformamide (4 mL) in a Schlenk vial was subjected to three cycles of evacuation backfilling with argon. Tetrakis(triphenylphosphine)palladium (0) (91 mg, 0.08 mmol) was then added and the resulting mixture was subjected to three further cycles of evacuation backfilling with argon before being stirred at 100 ºC for 20 hours. The reaction mixture was cooled down, the solvent was removed under reduced pressure and the residue was purified by flash chromatography (1:1 hexanes/ethyl acetate to 100% ethyl acetate) to give the title compound (131 mg, 64%) as a beige solid. LRMS (m/z): 262 (M+1)+.

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; Almirall, S.A.; EP2463289; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference 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.

Synthesis of intermediate IV-02IV-01 IV-02To a solution of 3-bromo-6-chIoroimidazo[1 ,2-b]pyridazine (IV-01) (450 mg, 1.936 mmol) in 1 ,4-dioxane (8 mL) was added 3-(N-Boc-aminomethyl)pyridine-5- boronic acid pinacol ester (679 mg, 2.033 mmol), aq. Na2C03 2 (3 mL, 6 mmol) and PdCI2(PPh3)2 (136 mg, 0.194 mmol). The resulting mixture was heated at 80 C in a sealed tube for 8 h. On cooling, the mixture was diluted with DC and water. Layers were separated and the aqueous phase was extracted twice with DCM. The combined organic extracts were dried (Na2S04), filtered and concentrated. The residue was purified by flash chromatography (Biotage) using MeOH:DCM 0:100 to 20:80 as eluent to afford intermediate IV-02 (525mg, 75%).

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; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); PASTOR FERNANDEZ, Joaquin; ALVAREZ ESCOBAR, Rosa Maria; RIESCO FAGUNDO, Rosario Concepcion; GARCIA GARCIA, Ana Belen; RODRIGUEZ HERGUETA, Antonio; MARTIN HERNANDO, Jose Ignacio; BLANCO APARICIO, Carmen; CEBRIAN MUNOZ, David Alvaro; WO2012/156756; (2012); A2;,
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. Formula: C6H3BrClN3

General procedure: The corresponding 3-Bromo-6-chloro-imidazopyridazine (1.0 eq) was suspended in dioxane (0.5 mUmmol) and the appropriate n- boc diamine (2.7 eq) or amino alcohol (3 eq) was added. The mixture was heated under mw irradiation at 160C for 2h. Water was added and the mixture was extracted with AcOEt. The organic phase was separated, dried (Na2S04), filtered and evaporated till dryness. The residue was purified by Biotage flash column chromatography (eluent: 4 to 6% MeOH in DCM) to give the desired product.

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; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); PASTOR FERNANDEZ, Joaquin; ALVAREZ ESCOBAR, Rosa Maria; VARELA BUSTO, Carmen; GARCIA GARCIA, Ana Belen; DIMITRIEVICH ZARICH, Natasha; BLANCO APARICIO, Carmen; RODRIGUEZ LOPEZ, Ana; OYARZABAL SANTAMARINA, Julen; BISCHOFF, James Robert; WO2013/1310; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 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.

13.9 g (59.8 mmol) 3-bromo-6-chloro-imidazo[1 ,2-6]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 100 C 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 dichioromethane 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, DM50-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).LCM5 (Method 1 ): Rt = 1 .35 min; MS (ESIpos) m/z = 270 [M+H]

Statistics shows that 3-Bromo-6-chloroimidazo[1,2-b]pyridazine is playing an increasingly important role. we look forward to future research findings about 13526-66-4.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; KNUT, Eis; PUeHLER, Florian; ZORN, Ludwig; SCHOLZ, Arne; LIENAU, Philip; GNOTH, Mark; BOeMER, Ulf; GUeNTHER, Judith; FANGHAeNEL, Joerg; KORR, Daniel; WO2012/163942; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics