Day: March 8, 2021

Electric Literature of 166526-03-0, 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. 166526-03-0, name is 4,6-Dichloronicotinonitrile, molecular formula is C6H2Cl2N2, 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.

[00404] Step 1 : A mixture of 4,6-dichloronicotinonitrile (760 mg, 4.39 mmol), (2S,3S)-3-amino-3-phenylpropane-l,2-diol (780 mg, 4.66 mmol) (Pico, Anna; Moyano, Albert ARKIVOC (Gainesville, FL, United States) (2007), (4), 132-156) and DIPEA (921 mu, 5.27 mmol) in DMA (4393 mu) was stirred at 50 C for 2.5 hours after which LCMS indicated -98% reaction completion. The vessel was cooled to room temperature and the dark solution was partitioned between ethyl acetate and water. The organic portion was washed with water and the combined aqueous layers were extracted with ethyl acetate. The organics were combined, dried over anhyrdous sodium sulfate, filtered and concentrated. The mixture was dissolved in 2 mL of DCM and purified on a 40G ISCO column using 5-100% EA/Heptane. Following concentration, the regioisomers were collected as isolates 01 and 02.

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 166526-03-0, 4,6-Dichloronicotinonitrile.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DODD, Dharmpal, S.; MUSSARI, Christopher, P.; BHIDE, Rajeev, S.; NAIR, Satheesh Kesavan; PAIDI, Venkatram Reddy; KUMAR, Sreekantha Ratna; BANERJEE, Abhisek; SISTLA, Ramesh; PITTS, William, J.; HYNES, John; WO2013/106614; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1001413-01-9, 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 1001413-01-9, name is 1-(3,4-Difluorobenzyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

Compound 57.5 (0.1 grams, 0.277 mmol) was suspended in toluene (2 ml) and chilled to 0 0C. 1.0M diisobutylaluminium hydride (0.304 ml) was added drop-wise and the reaction stirred overnight, allowing it to warm to room temperature. The reaction was quenched with a saturated aqueous solution of Rochelle’s salt, filtered through Celite, the layers separated, the organic layer washed with brine, dried over sodium sulfate, filtered, and concentrated. This residue was mixed with l-(3,4-Difluoro-benzyl)-2-oxo-l,2-dihydro-pyridine-3-carboxylic acid (73 milligrams, 0.277 mmol), N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (64 milligrams, 0.332 mmol), 1-hydroxybenzotriazole monohydrate (51 milligrams, 0.332 mmol), dissolved in N,N-dimethylformamide (2 ml) and diisopropylethylamine (0.241 ml, 1.39 mmol) was added. The reaction was stirred at ambient temperature for 16 hours and then flooded with ethyl acetate, washed with saturated sodium bicarbonate, brine, dried over sodium sulfate, filtered and concentrated to yield Compound 57.6 (90.7 milligrams, 0.148 mmol). ES (+) MS m/e = 613 (M+H).

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 1001413-01-9, 1-(3,4-Difluorobenzyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid.

Reference:
Patent; SUNESIS PHARMACEUTICALS; BIOGEN IDEC, INC.; WO2008/5457; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 78686-79-0, name is Methyl 5-bromo-2-chloronicotinate, the common compound, a new synthetic route is introduced below. name: Methyl 5-bromo-2-chloronicotinate

12A: Methyl 5-(2-acetamidoimidazo[1,2-b]pyridazin-6-yl)-2-chloronicotinate : A mixture of N-(6-chloroimidazo[1,2-b]pyridazin-2-yl)acetamide (300 mg, 1.424 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (579 mg, 2.279 mmol), PdCl2(dppf)-CH2Cl2 adduct (116 mg, 0.142 mmol) and potassium acetate (419 mg, 4.27 mmol) in dioxane (8 mL) was heated to 100 C for 6 h. The reaction mixture was allowed to cool to rt. To the stirred crude mixture was added methyl 5-bromo-2-chloronicotinate (392 mg, 1.565 mmol) and PdCl2(dppf)-CH2Cl2 adduct (58.1 mg, 0.071 mmol) and the mixture was degassed by bubbling nitrogen though the mixture for 5 min. Potassium carbonate (393 mg, 2.85 mmol) was quickly added and the reaction mixture heated at 100 C for 4 h. An additional 1/2 equivalent of bromide, catalyst and base were added and heating to 100 C was continued for 2 h. The reaction mixture was partitioned between EtOAc (75 mL) and water (75 mL). The organic layer was washed with brine (50 mL), dried (Na2S04) and concentrated to a residue that was chomato graphed on a 40 gm ISCO silica gel cartridge, eluting with a 0-10%MeOH/DCM gradient. The pure fractions were concentrated to afford methyl 5-(2-acetamidoimidazo[1,2-b]pyridazin-6-yl)-2-chloronicotinate (275 mg, 0.795 mmol, 55.9 % yield) as a yellow solid. 7968 MSESI m z 346.1/348.1 (M+H) NMR (500 MHz, DMSO-d6) delta 10.97 (s, 1H), 9.24 (d, J=2.2 Hz, 1H), 8.85 (d, J=2.5 Hz, 1H), 8.36 (s, 1H), 8.14 (d, J-8.8 Hz, 1H), 7.92 (d, J=9.4 Hz, 1H), 3.94 (s, 3H), 2.12 (s, 3H).

The synthetic route of 78686-79-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MERTZMAN, Michael E.; DZIERBA, Carolyn Diane; GUERNON, Jason M.; HART, Amy C.; LUO, Guanglin; MACOR, John E.; PITTS, William J.; SHI, Jianliang; SPERGEL, Steven H.; (245 pag.)WO2019/89442; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 15855-06-8, name is 2-Chloro-6-methoxypyridine-4-carboxylic Acid, the common compound, a new synthetic route is introduced below. Computed Properties of C7H6ClNO3

a) Sulfuric acid (1 mL) is added to a suspension of 2-chloro-6-methoxy-isonicotinic acid (4.16 g, 22.2 mmol) in ethanol (20 mL). The clear solution is stirred at 70 C. for 18 h. The mixture is neutralised by adding sat. aq. NaHCO3 solution and then extracted three times with EA (3*250 mL). The combined org. extracts are dried over MgSO4, filtered, concentrated and dried to give 2-chloro-6-methoxy-isonicotinic acid ethyl ester (4.32 g) as a white solid; LC-MS: tR=1.00 min, [M+1]+=215.89.

The synthetic route of 15855-06-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bolli, Martin; Lescop, Gyrille; Mathys, Boris; Mueller, Claus; Nayler, Oliver; Steiner, Beat; US2011/46170; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 131747-42-7, 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 131747-42-7, name is 6-(Trifluoromethyl)picolinic acid. This compound has unique chemical properties. The synthetic route is as follows.

Methanol was added to the reaction vessel under nitrogen atmosphere. 6-trifluoromethyl-pyridine-2-carboxylic acid (150 g, 0.785 mol) was added and dissolved at ambient temperature. Acetyl chloride (67.78 g, 0.863 mol) was added dropwise at a temperature below 45C. The reaction mixture was maintained at 65-70C for about 2-2.5 h, and then concentrated at 3 5-45C under vacuum and cooled to 25-35C. The mixture was diluted with ethyl acetate and rinsed with saturated NaHCO3 solution then rinsed with brine solution. The mixture was concentrated at 3 5-45C under vacuum and cooled to 25-35C, then rinsed with nheptane and concentrated at 3 5-45C under vacuum, then degassed to obtain brown solid, which was rinsed with n-heptane and stirred for 10-15 minute at 25-35C. The suspension was cooled to -40 to -3 0C while stirring, and filtered and dried to provide 6-trifluoromethyl-pyridine-2- carboxylic acid methyl ester.

According to the analysis of related databases, 131747-42-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CELGENE CORPORATION; AGIOS PHARMACEUTICALS, INC.; CHOPRA, Vivek, Saroj, Kumar; DIMARTINO, Jorge; KENVIN, Laurie, A.; KNIGHT, Robert, Douglas; MACBETH, Kyle; VISWANADHAN, Krishnan; XU, Qiang; AGRESTA, Samuel, V.; (135 pag.)WO2017/66611; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 13509-13-2, Adding some certain compound to certain chemical reactions, such as: 13509-13-2, name is Methyl 4-methylpicolinate,molecular formula is C8H9NO2, 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 13509-13-2.

Step 4. The preparation of 4-methyl-1-(3-methyl-butyl)-piperidine-2-carboxylic acid methyl ester: 4-Methyl-pyridine-2-carboxylic acid methyl ester (1.17 g, 7.74 mmol) was dissolved in acetic acid (50 mL), treated with PtO2 (0.5 g), and shaken under an atmosphere of H2 (50 psi) for thirty hours. The reaction mixture was evaporated under reduced pressure, then redissolved in EtOH (50 mL), treated with isovaleraldehyde (0.5 mL, 15 mmol) and 20% Pd/C (0.2 g), and shaken under H2 (50 psi) for twenty hours. The reaction was filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluding with 10% MeOH/CH2Cl2 to give 1.36 g (77%) of the desired product. MS: 228 (M+1 for C13H15N1O2).

According to the analysis of related databases, 13509-13-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Warner-Lambert; US6251919; (2001); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 52833-94-0, 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. 52833-94-0, name is 2-Amino-5-bromonicotinic acid, molecular formula is C6H5BrN2O2, 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.

A mixture of 2-Amino-5-bromo-nicotinic acid (1 g, 4.61 mmol) and SOd2 (5 mL) in toluene (15 mE) was stirred at 130C for 2 h. After concentrated, the residue was dissolved in tetrahydrofuran (20 mE), and then 2-fluoro-phenylamine (1.09 g, 9.81 mmol) was added dropwise at 0C. The reaction mixture was heated to 90C for 4 h. After being cooled to room temperature andquenched with saturated aqueous K2C03 (10 mE), the mixture was extracted with ethyl acetate (50 mE * 3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified with silica gel column chromatograph (PE : EtOAc = 2: 1) to give 2-amino-5-bromo-N-(2-fluorophenyl) nicotinamide (1.0 g, 70 % yield). as yellow solid. ?H-NMR (CDC13, 400 MHz) 8.258.28 (m, 2H), 7.86 (d, J 2.4 Hz, 2H), 7.137.22 (m, 3H), 6.36 (s, 2H). MS (M+H): 311 /313.

According to the analysis of related databases, 52833-94-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; NARGUND, Ravi; XIAO, Dong; ZORN, Nicolas; DANG, Qun; MCCOMAS, Casey C.; PENG, Xuanjia; LI, Peng; SOLL, Richard; WO2014/205593; (2014); A1;,
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. 1210419-26-3, name is Methyl 6-bromo-5-fluoropicolinate. A new synthetic method of this compound is introduced below., Safety of Methyl 6-bromo-5-fluoropicolinate

[0265] Pent-l-yne (0,524 g, 7,69 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.450 g, 0.64 mmol) was added to copper(I) iodide (0.122 g, 0,64 mmol), TEA (1.787 mL, 12.82 mmol) and methyl 6-bromo-5-fluoropicolinate (1.5 g, 6.41 mmol) in acetonitrile (20 mL) under nitrogen. The resulting mixture was stirred at 80 C for 3 hours. The solvent was removed under reduced pressure. The crude product was purified by flash silica chromatography, elution gradient 0 to 10% EtOAc in petroleum ether. Pure fractions were evaporated to dryness to afford methyl 5-fluoro-6-(pent-l-yn-l-yl)picolinate (1.28 g, 90 %) as a orange solid. XH NMR (400 MHz, CDCb) delta ppm 8.20 – 8.06 (m, 2H), 7.52 (dd, J = 8.6, 8.0 Hz, 2H), 4.14 (q, J = 7.1 Hz, 1H), 4.01 (s, 7H), 2.50 (td, J = 7.1, 1.0 Hz, 4H), 2.07 (s, 1H), 1.71 (h, J = 7.3 Hz, 4H), 1.28 (t, J = 7.1 Hz, 1H), 1.09 (t, J = 7.4 Hz, 6H). LC-MS (Method A): m/z (ES+), [M+H]+ = 222.2; acid, HPLC tR = 1.140 min.

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, 1210419-26-3, Methyl 6-bromo-5-fluoropicolinate.

Reference:
Patent; ASTRAZENECA AB; CUMMING, John, Graham; WU, Frank, Xinhe; EDMAN, Karl, Henrik; CHEN, Hongming; BROWN, Dean, Gordon; BURLI, Roland, Werner; JOHNSTONE, Shawn, Donald; BROWN, Giles, Albert; TEHAN, Benjamin, Gerald; TEOBALD, Barry, John; CONGREVE, Miles, Stuart; (187 pag.)WO2017/194716; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 13575-41-2, Thiazolo[4,5-b]pyridin-2-amine, 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, 13575-41-2, blongs to pyridine-derivatives compound. Quality Control of Thiazolo[4,5-b]pyridin-2-amine

(4) 15.7 g of isoamyl nitrite was added dropwise to a solution of 8.1 g of compound 4 in 160 ml of dry tetrahydrofuran(20min), and then heated to 65 degrees reflux 4h; TLC detection reaction should be terminated, down to room temperature, filter out nothing,Filter cake ethyl acetate (50 mL * 3), spin dry system, purified by column (200-300 mesh silica gel column) petroleum ether:Ethyl acetate = 1: 1),(Product 5) was obtained in a yield of 46.6%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13575-41-2, its application will become more common.

Reference:
Patent; Sphinx Scientific Laboratory (Tianjin) Co., Ltd.; Yao, Qingjia; Xu, Yangjun; Wu, Simin; (6 pag.)CN104402910; (2017); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 113770-88-0, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.113770-88-0, name is 3-Fluoro-4-cyanopyridine, molecular formula is C6H3FN2, molecular weight is 122.1, as common compound, the synthetic route is as follows.

3-Fluoroisonicotinonitrile (CAS ii3770-88-0, 68.4 mg, 0.56 mmol) and tert-butyl piperazinei-carboxylate (CAS 76535-74-5, 2i9 mg, i.i8 mmol) were dissolved in toluene in a microwave vial before flushed with Ar(g) and heated in a microwave reactor for is mm atiOOC. The reaction was diluted with EtOAc and filtered through a plug of silica. The filtrate was reduced in vacuo to give tert-butyl 4-(4-cyanopyridin-3-yl)piperazine-i-carboxylate (i53 mg, 95%).MS (ESI) m/z i89.0 [(M-Boc)-i-H]

Statistics shows that 113770-88-0 is playing an increasingly important role. we look forward to future research findings about 3-Fluoro-4-cyanopyridine.

Reference:
Patent; ACTURUM LIFE SCIENCE AB; SVENSSON, Mats A; WEIGELT, Dirk; WO2014/184248; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem