Category: 6188-23-4

Synthetic Route of 6188-23-4 , The common heterocyclic compound, 6188-23-4, name is 6-Bromoimidazo[1,2-a]pyridine, molecular formula is C7H5BrN2, 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 stirred solution of 38A (1.0 g, 5.08 mmol) in THF (60 mL) under argoncondition was added NaH (0.122 g, 5.08 mmol, 60 % in mineral oil). The reactionmixture was stirred at RT for 30 mm. and to it was added Selectfluor (3.87 g, 10.92 mmol) in acetonitrile (10 mL). The reaction mixture was heated at 70 C for another 20 h. The reaction mixture was quenched with saturated aq. NH4C1 solution (100 mL) and was extracted with ethyl acetate (3 x 100 mL). The combined organic layers were dried overanhydrous sodium sulfate, filtered and the filtrate evaporated under reduced pressure to get a brown gum. The crude product was purified by silica gel chromatography (24 g RediSep column, eluting with a gradient of 17-19 % EtOAc in petroleum ether). Fractions containing the desired product were combined and evaporated under reduced pressure to afford intermediate 38B (0.1 g, 9.16 % yield). LCMS: m/z = 215.3 [M+HjHPLC Ret. Time 0.37 mm. (HPLC Method D).

The synthetic route of 6188-23-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BORZILLERI, Robert M.; LIU, Peiying; TEBBEN, Andrew J.; VELAPARTHI, Upender; RAHAMAN, Hasibur; TONUKUNURU, Gopikishan; WARRIER, Jayakumar Sankara; (264 pag.)WO2018/17633; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6188-23-4, 6-Bromoimidazo[1,2-a]pyridine, 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, Recommanded Product: 6188-23-4, blongs to pyridine-derivatives compound. Recommanded Product: 6188-23-4

A mixture of the compound of example 1 (1.0 g, 5.08 mmol) and t-butyl 4-(5-(4, 4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1-carboxylate (1.97 g, 5.08 mmol) were treated with [1 ,1 ‘-bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.124 g, 0.152 mmol) and sodium carbonate (2.15 g, 20.30 mmol) in dry dimethylformamide (100 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 1.05 g (54.68 %); 1H NMR (DMSO-d6, 300 MHz): delta 1.39 (s, 9H, 3CH3), 3.44 (s, 4H, 2CH2), 3.55 (s, 4H, 2CH2), 6.95 (d, 1H, J=8.7 Hz, Ar), 7.50-7.62 (m, 3H, Ar), 7.87 (d, 1H, J=2.4 Hz, Ar), 7.90 (s, 1H, Ar), 8.46 (d, 1H, J=2.4 Hz, Ar), 8.83 (s, 1H, Ar); MS (ES+): m/e 380 (M+1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6188-23-4, 6-Bromoimidazo[1,2-a]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; PIRAMAL ENTERPRISES LIMITED; SHARMA, Rajiv; GHOSH, Usha; MORE, Tulsidas; KULKARNI, Mahesh; BAJAJ, Komal; BURUDKAR, Sandeep; RIZVI, Zejah; WO2014/80241; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 6188-23-4 , The common heterocyclic compound, 6188-23-4, name is 6-Bromoimidazo[1,2-a]pyridine, molecular formula is C7H5BrN2, 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.

Step: 1 To a solution of 6-bromoimidazo [l ,2-a]pyridine (20 g, 101.5 mmol) in ACN (300 mL) was added N-iodosuccinimide (22.8 g, 101.5 mmol) at rt and stirred for 5 h. The reaction mixture was filtered and washed with hot acetonitrile to afford 6-bromo-3-iodoimidazo[l,2- ajpyridine (22 g, 67%) as a pale yellow solid. 1H NMR (400 MHz, CDC13) delta 8.29 (s, 1H), 7.58 (d, J= 9.2 Hz, 1H), 7.35 (d, J= 7.6 Hz, 1H), 7.27 (s, 1H).

The synthetic route of 6188-23-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; NACRO, Kassoum; DURAISWAMY, Athisayamani, Jeyaraj; CHENNAMANENI, Lohitha, Rao; WO2013/147711; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6188-23-4, 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 6188-23-4 as follows.

To a solution of 6-bromoimidazo[1,2-a]pyridine (318 mg, 1.61 mmol) in 1,4-dioxane (15 mL) were added N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)cyclopropanesulfonamide (600 mg, 1.69 mmol), KOAc (316 mg, 3.22 mmol), H2O (3 mL) and Pd(dppf)Cl2.CH2Cl2 (131 mg, 0.161 mmol). The reaction was heated to 85 C. and stirred further for 5 hours under N2 atmosphere, then cooled to rt, and concentrated in vacuo. The residue was dissolved in DCM (200 mL) and the resulted mixture was filtered through a CELITE. The filtrate was washed with H2O (100 mL) and brine (100 mL). The combined aqueous layers were extracted with DCM (50 mL*3). The combined organic extracts were dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by a flash silica gel column chromatography (DCM/MeOH (v/v)=65/1) to give the title compound as a yellowish solid (342 mg, 62%). MS (ESI, pos. ion) m/z: 345.0 [M+H]+; 1H NMR (600 MHz, DMSO-d6): delta 9.42 (s, 1H), 8.91 (s, 1H), 8.35 (d, J=2.1 Hz, 1H), 7.99 (s, 1H), 7.93 (d, J=2.4 Hz, 1H), 7.68-7.61 (m, 2H), 7.54 (dd, J=1.8, 9.6 Hz, 1H), 3.98 (s, 3H), 2.82-2.74 (m, 1H), 1.00-0.89 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6188-23-4, its application will become more common.

Reference:
Patent; Calitor Sciences, LLC; Xi, Ning; US2014/134133; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 6188-23-4 ,Some common heterocyclic compound, 6188-23-4, molecular formula is C7H5BrN2, 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.

EtOH (1.8 mL) was added into a mixture of 4-bromo-3-ethylpyridinehydrobromide (49 mg, 0.18 mmol), B2(OH)4 (49 mg, 0.55 mmol), XPhos-Pd-G2 (14 mg, 0.018 mmol), XPhos (17 mg, 0.037 mmol), and KOAc (54 mg, 0.55 mmol). The reaction was degassed via N2 and stirred at 80C overnight. After cooling to room temperature, solutions of N-(2-(3-bromophenyl)propan-2-yl)-2-(trifluoromethyl)benzenesulfonamide (Intermediate 1J) (100 mg, 0.24 mmol) in EtOH/THF (0.3 mL/0.3 mL) and K2C03 (1.8 M, 0.31 mL, 0.55 mmol) were added respectively into the reaction. The mixture was degassed via N2 again and stirred at 85C overnight. The reaction was cooled to room temperature, filtered through celite, washed with EtOAc (3X), and concentrated in vacuo to give a residue which was dissolved into EtOAc. This solution was washed with brine (IX), dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by MS-HPLC to afford the title compound (16 mg, 20%). LCMS (method A): m/z 449.3 (M+H)+. NMR (CDC13) delta 8.54 (s, 1H), 8.46 (d, 1H), 7.83 (d, 1H), 7.79 (d, 1H), 7.59 (t, 1H), 7.47 (t, 1H), 7.31 (m, 2H), 7.21 (t, 1H), 7.11 (dt, 1H), 7.03 (d, 1H), 5.28 (s, 1H), 2.63 (q, 2H), 1.69 (s, 6H), 1.13 (t, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6188-23-4, its application will become more common.

Reference:
Patent; VENENUM BIODESIGN LLC; HUANG, Chia-Yu; SHI, Dongchuan; KULTGEN, Steven G.; MCGUINNESS, Brian F; LETOURNEAU, Jeffrey J.; COLE, Andrew G.; BEASLEY, James R.; (358 pag.)WO2018/5801; (2018); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 6188-23-4 ,Some common heterocyclic compound, 6188-23-4, molecular formula is C7H5BrN2, 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.

EtOH (1.8 mL) was added into a mixture of 4-bromo-3-ethylpyridinehydrobromide (49 mg, 0.18 mmol), B2(OH)4 (49 mg, 0.55 mmol), XPhos-Pd-G2 (14 mg, 0.018 mmol), XPhos (17 mg, 0.037 mmol), and KOAc (54 mg, 0.55 mmol). The reaction was degassed via N2 and stirred at 80C overnight. After cooling to room temperature, solutions of N-(2-(3-bromophenyl)propan-2-yl)-2-(trifluoromethyl)benzenesulfonamide (Intermediate 1J) (100 mg, 0.24 mmol) in EtOH/THF (0.3 mL/0.3 mL) and K2C03 (1.8 M, 0.31 mL, 0.55 mmol) were added respectively into the reaction. The mixture was degassed via N2 again and stirred at 85C overnight. The reaction was cooled to room temperature, filtered through celite, washed with EtOAc (3X), and concentrated in vacuo to give a residue which was dissolved into EtOAc. This solution was washed with brine (IX), dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by MS-HPLC to afford the title compound (16 mg, 20%). LCMS (method A): m/z 449.3 (M+H)+. NMR (CDC13) delta 8.54 (s, 1H), 8.46 (d, 1H), 7.83 (d, 1H), 7.79 (d, 1H), 7.59 (t, 1H), 7.47 (t, 1H), 7.31 (m, 2H), 7.21 (t, 1H), 7.11 (dt, 1H), 7.03 (d, 1H), 5.28 (s, 1H), 2.63 (q, 2H), 1.69 (s, 6H), 1.13 (t, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6188-23-4, its application will become more common.

Reference:
Patent; VENENUM BIODESIGN LLC; HUANG, Chia-Yu; SHI, Dongchuan; KULTGEN, Steven G.; MCGUINNESS, Brian F; LETOURNEAU, Jeffrey J.; COLE, Andrew G.; BEASLEY, James R.; (358 pag.)WO2018/5801; (2018); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – 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. 6188-23-4, name is 6-Bromoimidazo[1,2-a]pyridine. A new synthetic method of this compound is introduced below., Recommanded Product: 6-Bromoimidazo[1,2-a]pyridine

B. 3-Nitro-6-bromoimidazo [1,2-a] pyridine A solution of 24 gms. (.122 mole) of 6-bromoimidazo [1,2-a] pyridine in 80 ml. of concentrated sulfuric acid is treated dropwise with 24 ml. of concentrated nitric acid while maintaining a temperature of 15 C. with external cooling. When the addition is complete, the reaction mixture is stirred at room temperature for 1/2 hour and poured onto 450 gm. of ice. The ph of the mixture is adjusted to ph 4 with aqueous potassium hydroxide and the resultant solids are collected by filtration. The filter cake is washed with water and dried. Recrystallization from methylene chloride-hexane yields pure 3-nitro 6-bromoimidazo [1,2-a] pyridine m.p. 160-161 C.

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, 6188-23-4, 6-Bromoimidazo[1,2-a]pyridine.

Reference:
Patent; Merck & Co., Inc.; US4096264; (1978); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 6188-23-4 ,Some common heterocyclic compound, 6188-23-4, molecular formula is C7H5BrN2, 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.

Example 896-(lmidazo[1,2-a]pyridin-6-ylethynyl)-2,2-dimethyl-2H-pyrano[2,3-b]pyridin-4(3H)- one [00270] A mixture of 6-bromoimidazo[1 ,2-a]pyridine (4.00 g, 20.30 mmol), ethynyltrimethylsilane (2.98 g, 30.30 mmol), PdCI2[PPh3]2 (460 mg, 0.66 mmol), Cul (380 mg, 2.02 mmol), and TEA (8.4 mL, 60.9 mmol) in benzene (25 mL) is stirred at 50 C under argon atmosphere for 8 h, cooled down to r.t. and concentrated at reduced pressure. The obtained residue is purified by column chromatography (silica gel, EtOAc/hexane) to give 6-((trimethylsilyl)ethynyl)imidazo[1 ,2-a]pyridine (3.20 g, 74%) as yellow solid.[00271 ]TBAF solution in THF (1 M, 1 .04 mL, 1 .04 mmol) is added dropwise to a solution of 6-((trimethylsilyl)ethynyl)imidazo[1 ,2-a]pyridine (3.20 g, 14.90 mmol) in THF (20 mL) at 0 C. The resulting mixture is stirred at 0 C for 1 h, diluted with water and extracted with DCM (3×30 mL). The combined organic phases were dried over Na2S04 and concentrated at reduced pressure. The obtained residue was purified by column chromatography (silica gel, EtOAc/hexane) to give 6-ethynylimidazo[1 ,2-a]pyridine (1 .37 g, 65%) as brown oil.[00272]According to General Procedure 1 , 6-bromo-2,2-dimethyl-2/-/-pyrano[2,3- b]pyridin-4(3/-/)-one (256 mg, 1 .0 mmol) is reacted with 6-ethynylimidazo[1 ,2-a]pyridine (156 mg, 1 .1 mmol) in the presence of PdCI2[PPh3]2 (35 mg, 0.05 mmol), P(f-Bu)3 (10 mg, 0.05 mmol), DBU (15 mg, 0.1 mmol), and TEA (2 mL) in acetonitrile (10 mL) at reflux for 6 h. The crude product is purified by column chromatography (silica gel, EtOAc/hexane) to provide the title compound (123 mg, 39%).1H NMR (De-DMSO), deltaEta, 1 .47 (s, 6H), 2.92 (s, 2H), 7.32 (d, 1 H), 7.60 (d, 1 H), 7.64 (s, 1 H), 7.96 (s, 1 H), 8.24 (s, 1 H), 8.66 (s, 1 H), 8.92 (s, 1 H).LC/MS (M+H)+ = 318

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. 6188-23-4, 6-Bromoimidazo[1,2-a]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERZ PHARMA GMBH & CO. KGAA; HENRICH, Markus; ABEL, Ulrich; MULLER, Sibylle; KUBAS, Holger; MEYER, Udo; HECHENBERGER, Mirko; KAUSS, Valerjans; ZEMRIBO, Ronalds; WO2012/52451; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – 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. 6188-23-4, name is 6-Bromoimidazo[1,2-a]pyridine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 6188-23-4

Step 1: To a solution of 4-(ethoxycarbonyl)-3-fluorophenylboronic acid ( 1.29 g, 6.091 mmol), K3P04 (3.22 g, 15.22 mmol) in 1,4-dioxane (20 mL), and water (3 mL) was added 6- bromoimidazo[l,2-a]pyridine (1 g, 5.07 mmol) and degassed with argon for 30 min. (A- Phos)2PdCl2 (293 mg, 0.25 mmol) was added and again degassed with argon for 30 min and the reaction mixture was heated at 90 C for overnight. The reaction mixture was washed with water. The organic layer was concentrated and the crude product was purified by column chromatography (silica gel, eluent CHCl3/MeOH 96.5: 3.5) to afford 2-fluoro-4- (imidazo[l,2-a]pyridin-6-yl)benzoate (1.16 g, 81%, AUC LC-MS 84%). 1H NMR (300 MHz, DMSO- 6) ppm delta 9.1 (s, 1 H), 7.9 (m, 2 H), 7.6 (m, 5 H), 4.3 (q, J= 6.9 Hz, 2 H), 1.3 (t, J= 6.9 Hz, 3 H); MS (ESI) m/z 285 (M+l).

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, 6188-23-4, 6-Bromoimidazo[1,2-a]pyridine.

Reference:
Patent; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; NACRO, Kassoum; DURAISWAMY, Athisayamani, Jeyaraj; CHENNAMANENI, Lohitha, Rao; WO2013/147711; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem