Day: July 5, 2021

Electric Literature of 13466-38-1, 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. 13466-38-1, name is 5-Bromopyridin-2-ol, molecular formula is C5H4BrNO, The 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.

Example 140 To a suspension of NaH (60% dispersion in mineral oil, 1.34 g, 0.056 mol) in THF (10 mL), a solution of 5-bromopyridin-2-ol (2.5 g, 0.014 mol) in THF (50 mL) was added and the resulting mixture was stirred at RT for 1 h. To this mixture, iodoethane (10.9 g, 0.07 mol) was added and the mixture was stirred at RT overnight. The mixture was quenched with water and washed with NH4Cl solution. The organic phase was separated, then concentrated in vacuo and the residue was purified by flash chromatography on silica gel (50-100% PE-AE) to afford 5-bromo-1-ethylpyridin-2(1H)-one.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 13466-38-1, 5-Bromopyridin-2-ol.

Reference:
Patent; INTELLKINE, LLC; INFINITY PHARMACEUTICALS, INC.; CASTRO, Alfredo C.; EVANS, Catherine A.; JANARDANANNAIR, Somarajannair; LESCARBEAU, Andre; LIU, Tao; SNYDER, Daniel A.; TREMBLAY, Martin R.; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; US2013/53362; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6937-03-7, 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 6937-03-7 as follows.

To solution of (2,4,5-trichloro-phenoxy)-acetic acid (150 mg, 0.59 mmol), 2-amino isonicotinic acid methyl ester (179 mg, 1.18 mmol) and DMAP (144 mg, 1.18 mmol) in DMF 13 mL was added PyBOP (614 mg, 1.18 mmol) at room temperature. Reaction mixture was stared at room temperature. Resulting mixture poured onto ice cold water, was diluted by ethyl acetate. The organic phase was separated, sequentially washed with aqueous sodium bicarbonate, brine and water, dried over anhydrous MgSO4, and concentrated. The residue was purified by flash silica gel column chromatography (EtoAC:Hexane=1:1) to give 2-[2-(2,4,5-trichloro-phenoxy)-acetylamino]-isonicotinic acid methyl ester as a colorless solid (0.056 g, 24.45% yield). 1H NMR (DMSO-d6, 300 MHz) 10.89 (1H, s, CONH), 8.54 (2H, d, J=5.4 Hz, pyridine), 7.85 (s, 1H, aromatic), 7.58 (1H, dd, J=1.35 &4.95 Hz, pyridine), 7.48 (1H, s, aromatic), 5.05 (2H, s, OCH2), 3.89 (3H, s, OCH3).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6937-03-7, its application will become more common.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY; US2009/306078; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 16110-09-1, 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 16110-09-1 as follows.

Step 1 Synthesis of Ethyl 5-chloropyridin-2-carboxylate: 1.2 g (8.2 mmol) of 2,5-dichloropyridine was dissolved in 50 ml of acetonitrile. 1.46 g (9.7 mmol) of sodium iodide and 0.7 ml (9.7 mmol) of acetyl chloride were added to the obtained solution, and they were stirred at 50 C. overnight. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the obtained crude product was dissolved in 15 ml of DMF. 182 mg (0.8 mmol) of palladium acetate, 147 mg (0.56 mmol) of triphenylphosphine, 2.3 ml of ethanol and 1.3 ml (9.7 mmol) of triethylamine were added to the obtained solution, and they were stirred in the presence of carbon monoxide at 70 C. overnight. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the obtained crude product was purified by the silica gel column chromatography to obtain the title compound. Yield: 250 mg (1.35 mmol) (16%) H-NMR (CD3Cl) delta 1.44 (3H, t), 4.47 (2H, d), 7.82 (1H, dd), 8.09 (1H, d), 8.69 (1H, d)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16110-09-1, its application will become more common.

Reference:
Patent; AJINOMOTO CO. INC; US2003/186969; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 52568-28-2 ,Some common heterocyclic compound, 52568-28-2, molecular formula is C8H12N2, 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: To a solution of the acid (1 equiv.) in DCM (0.2 M) were added EDCI (1.2 equiv.), HOBt (1.2 equiv.), DIPEA (1.2 equiv.) at 0 C. After the mixture was stirred for 10 min, the amine (1.2 equiv.) was added. The reaction was stirred overnight at room temperature. Then water was added and the mixture was extracted with DCM. The combined organic layer was washed with saturated NaHCO3, brine, dried over Na2SO4 and concentrated. The crude product was purified by flash column chromatography on silica gel 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,52568-28-2, its application will become more common.

Reference:
Article; Wang, Haifeng; Niu, Youhong; Zhang, Guoying; Ye, Xin-Shan; Tetrahedron Letters; vol. 57; 41; (2016); p. 4544 – 4548;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 156072-86-5, 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. 156072-86-5, name is 5-Bromo-3-methylpicolinonitrile. A new synthetic method of this compound is introduced below.

Step B 5-bromo-3-methylpyridine-2-carboxylic acid To a solution of 5-bromo-3-methylpyridine-2-carbonitrile (3.9 g, 20 mmol) in ethanol (30 mL) was added 6.0 M sodium hydroxide in water (15 mL), and the reaction was stirred at 80 C. for 1.5 h. The reaction mixture was concentrated, diluted with water and partitioned in EtOAc. The aqueous phase was acidified to pH 2-3. The product then was extracted with EtOAc, washed with brine, dried over sodium sulfate, filtered and concentrated to give 4.2 g (98% yield) of the desired product as a yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,156072-86-5, 5-Bromo-3-methylpicolinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Incyte Corporation; Huang, Taisheng; Feng, Hao; Kong, Lingquan; Wang, Anlai; Ye, Hai Fen; US2013/96144; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 6443-85-2 ,Some common heterocyclic compound, 6443-85-2, molecular formula is C7H6N2, 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.

A mixture of 2-(pyridin-3-yl)acetonitrile (1 g, 8.47 mmol, 1.00 equiv), Raney nickel (1 g, 17.24 mmol, 1.00 equiv) and ammonium hydroxide (3 mL) in methanol (15 mL) was stirred under 1 atmosphere of hydrogen at room temperature overnight. The catalyst was removed by filtration through a pad of Celite and washed with several portions of methanol. The filtrate and washings were combined and concentrated under vacuum to give 940 mg (45%) of 2-(pyridin-3-yl)ethanamine as a yellow oil. LC-MS: (ES, m/z): 164 [M+CH3CN+H]+, 123 [M+H]+, 106.

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. 6443-85-2, 2-(Pyridin-3-yl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The Board of Trustees of the Leland Stanford Junior University; Auckland UniServices Limited; Ruga Corporation; Giaccia, Amato; Lai, Edwin; Razorenova, Olga; Chan, Denise; Hay, Michael Patrick; Bonnet, Muriel; Sun, Connie; Tabibiazar, Ray; Yuen, Po-wai; US2015/329503; (2015); A1;,
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

Related Products of 117007-52-0 , The common heterocyclic compound, 117007-52-0, name is 3-Iodo-1H-pyrazolo[3,4-b]pyridine, molecular formula is C6H4IN3, 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.

Compound (M-2) was dissolved in THF (8.4 mL)TEA (234 muL, 1.68 mmol),(Boc) 2 O (289 muL, 1.26 mmol) and DMAP(10.3 mg, 0.0839 mmol) were sequentially added,And the mixture was stirred at room temperature for 1 hour.Water was added to the reaction solution, and the mixture was extracted with ethyl acetate.The organic layer was washed with water,And then washed successively with saturated brine,After drying with anhydrous sodium sulfate, filtration was carried out.After distilling off the solvent under reduced pressure,The residue was purified by silica gel column chromatography (n-hexane: ethyl acetate)Compound (VII-10)(Yield 151 mg, Yield 52%)As a white solid.

The synthetic route of 117007-52-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kaken Pharmaceutical Co., Ltd.; Watanabe, Atsushi; Sato, Yuki; ogura, Keiji Tamada; Tatsumi, Yoshiyuki; (283 pag.)JP2018/145180; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 152460-10-1, name is N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine. This compound has unique chemical properties. The synthetic route is as follows. name: N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine

Embodiment 2 In a 5000 ml dried 4-neck flask, 3000 ml dichloromethane,277 g 4-methyl-N-3-(4-pyridin-3-yl-pyrimidin-2-yl)-1,3-benzenediamine, and 270 g 4-(4-methyl-piperazin-1-methyl)-benzoic acid ethyl ester were added. After it was stirred to dissolve, 100 g sodium methoxide was then added. The mixture was heated to 40 C. for reflux and reaction overnight until the reaction was detected to be complete, and then was concentrated to remove toluene. The residue solid was washed with water and dried, thus 455 g Imatinib was obtained, and the yield was 92.0%. The data of spectrum is the same as above.

With the rapid development of chemical substances, we look forward to future research findings about 152460-10-1.

Reference:
Patent; Shen, Xin; He, Xiao; Yang, Jidong; Wu, Shaohong; Zhan, Huaxing; US2013/41149; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 153034-90-3, name is 2-Chloro-4-iodonicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H3ClINO

The following compounds were dissolved in a mixed solution of 200 ml of toluene, 100 ml of ethanol, and 100 ml of a 2-normal aqueous sodium carbonate solution.Compound 1-1: 3.83 g (14.3 mmol)Compound 4-4: 4.0 g (12.9 mmol)While the resulting reaction solution was stirred at a room temperature in a nitrogen atmosphere, 0.83 g (0.72 mmol) of tetrakis(triphenylphosphine)palladium(0) was added in the reacting solution. The reaction solution was heated to 60 degrees Celsius and then stuffed for 7 hours. After the reaction was completed, water was added to the reaction solution. The organic layer was extracted with toluene and dried with anhydrous sodium sulfate. Subsequently, the solvent was distilled off under reduced pressure. The residue was purified by column chromatography (gel used in chromatography: BW300 (produced by Fuji Silysia Chemical Ltd.), developing solvent:ethyl acetate/heptane = 1/2) and washed with methanol. Thus, 1.6 g (yield 38%) of Compound 4-5 was prepared.

With the rapid development of chemical substances, we look forward to future research findings about 153034-90-3.

Reference:
Patent; CANON KABUSHIKI KAISHA; ABE, Shigemoto; KAMATANI, Jun; KISHINO, Kengo; SAITOH, Akihito; YAMADA, Naoki; KOSUGE, Tetsuya; HORIUCHI, Takayuki; NISHIDE, Yosuke; MIYASHITA, Hirokazu; WO2014/115528; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem