Category: pyridine-derivatives

Related Products of 129768-95-2, 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. 129768-95-2, name is (4-Methylpyridin-2-yl)methanamine. A new synthetic method of this compound is introduced below.

4-methyl-2-(pyrrolidin-2-one-1-yl)methyl pyridine g 3.66 (0.03 moles) of 4-methyl-2-aminomethyl pyridine were dissolved in 60 ml of dry CHCl3, ml 16.8 of triethylamine were added and the resulting solution was cooled at -20C. g 4 (0.036 moles) of 4-chlorobutyrroylchloride were then dropped in, on stirring and cooling, at such a rate to keep the temperature at -20C. The reaction was completed by stirring at room temperature for 2 hours, TLC CHCl3/MeOH/NH3; 94.5/5/0.5. The reaction mixture was poured in 40 ml of 20% Na2CO3; the organic layer was separated and the aqueous layer was extracted twice with CH2Cl2. The collected organic phases were dried on Na2SO4, filtered and evaporated i.v. The crude oil obtained was dissolved in 300 ml THF dry and under nitrogen atmosphere, at 0C, g 1.3 of NaH 80% and ml 1 of HMPT were added.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,129768-95-2, (4-Methylpyridin-2-yl)methanamine, and friends who are interested can also refer to it.

Reference:
Patent; Smithkline Beecham Farmaceutici S.p.A.; EP447704; (1991); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 192447-58-8, 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. 192447-58-8, name is 2,6-Dibromo-N,N-dimethylpyridin-4-amine, molecular formula is C7H8Br2N2, 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.

(1) Production of 2-bromo-4-dimethylamino-6-[3-(trifluoromethyl)phenoxy] pyridine as an intermediate 3-(trifluoromethyl) phenol (1.4 g, 0.0071*1.2 mol) was dissolved in DMF (about 20 ml). Further, sodium hydride (0.30 g (ca. 60% in mineral oil), 0.0071*1.06 mol) and then 2,6-dibromo-4-dimethylamino pyridine (2.00 g, 0.0071 mol) were added to the obtained solution. The resultant solution was refluxed for about 6 hours, and thereafter allowed to stand for cooling to room temperature. The obtained reaction solution was distributed in hexane-saturated sodium bicarbonate water. The organic phase separated from the solution was washed with saturated brine, dried with anhydrous sodium sulfate, concentrated and purified by silica gel column chromatography (eluding solution: ethyl acetate/hexane). The purified product was subjected recrystallization using hexane, thereby obtaining an aimed product. Yield weight: 1.67 g; yield percentage: 65%; solid; melting point: 61 to 66 C.; 1H-NMR (60 MHz, CDCl3, delta): 2.86 (6H, s), 6.88 (1H, d, J=2 Hz), 6.38 (1H, d, J=2 Hz), 6.9-7.5 (4H, complex).

According to the analysis of related databases, 192447-58-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kureha Kagaku Kabushiki Kaisha; US6200933; (2001); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 19346-44-2, 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 19346-44-2, name is 2-Fluoro-3-nitro-5-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

LiHMDS l.5M in THF (2.6 mL; 3.84 mmol) was added dropwise at 5C to a solutionof 4-methyl-3-(hydroxymethyl)morpholine (420 mg; 3.20 mmol) in Me-THF (12 mL).After 30 mi 2-fluoro-5-methyl-3-nitropyridine (500 mg; 3.20 mmol) was quickly added and the reaction mixture was allowed to warm to room temperature and stirredrt overnight. LiHMDS 1 .5M in THF (854 p1; 1.28 mmol) was added at 0C and the mixture was stirred at rt for 5h. The reaction mixture was poured onto iced water, a10% aqueous solution of K2C03 and extracted with EtOAc. The organic layer was decanted, washed with water, dried over MgSO4, filtered and evaporated to give 733 mg of crude. The crude was purified by chromatography over silica gel (SiOH, GraceResolv, 12 g, Mobile phase DCM/MeOH/NH4OH, Gradient from: 99% DCM, 1% MeOH, 0.1% NH4OH to 97% DCM, 3% MeOH, 0.3% NH4OH). The pure fractionswere collected and the solvent was evaporated to give 544 mg of intermediate 445 (64% yield, yellow solid).

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 19346-44-2, 2-Fluoro-3-nitro-5-methylpyridine.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier Alexis Georges; GROSS, Gerhard Max; JACOBY, Edgar; MEERPOEL, Lieven; KULAGOWSKI, Janusz Jozef; MACLEOD, Calum; MANN, Samuel Edward; GREEN, Simon Richard; HYND, George; (476 pag.)WO2017/125534; (2017); 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. 902837-39-2, name is 3-Bromo-5-iodopyridin-4-amine. This compound has unique chemical properties. The synthetic route is as follows. name: 3-Bromo-5-iodopyridin-4-amine

(E)-4-(4-Amino-5-bromopyridin-3-yl)but-3-en-2-one To a solution of 3-Bromo-5-iodopyridin-4-amine (150 mg, 0.502 mmol) in DMF (1.5 mL) were added 3-buten-2-one (0.061 mL, 0.753 mmol), triethylamine (0.097 mL, 0.703 mmol), tri-o-tolylphosphine (12 mg, 0.040 mmol) and palladium(II)acetate (4.51 mg, 0.020 mmol) under nitrogen. The mixture was stirred at 90 C. overnight before it was diluted with water and EtOAc and the layers were separated. The organic layer was washed with water, dried over MgSO4, filtered and the filtrate concentrated in vacuum. The resulting brown oil was purified by chromatography on silica gel (biotage, CH2Cl2/EtOH, 100:0 to 94:6) to give the product (51 mg, purity around 60%) as a yellow solid, which was used in the next step without further purification.

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, 902837-39-2, 3-Bromo-5-iodopyridin-4-amine.

Reference:
Patent; Merck Patent GmbH; Cancer Research Technology, Ltd.; SCHIEMANN, Kai; BLAGG, Julian; MALLINGER, Aurelie; RINK, Christian; SEJBERG, Jimmy; HONEY, Mark; (139 pag.)US2016/16951; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 118289-16-0, 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 118289-16-0, name is 2-Bromopyridine-4-methanol. This compound has unique chemical properties. The synthetic route is as follows.

149 g (1714 mmol) of manganese dioxide is added in measured quantities to 28.0 g (148.9 mmol) of 2-bromo-4-hydroxymethyl-pyridine in 500 ml of dichloromethane within 6 hours. Then, stirring is continued at room temperature for 48 hours. It is suctioned off over Celite and concentrated by evaporation. 16.4 g of solidifying white oil accumulates.

According to the analysis of related databases, 118289-16-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Huth, Andreas; Zorn, Ludwig; Krueger, Martin; Ince, Stuart; Thierauch, Karl Heinz; Menrad, Andreas; Haberey, Martin; Hess-Stumpp, Holger; US2005/54654; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 722550-01-8, 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.722550-01-8, name is 4-(Pyrrolidin-1-yl)pyridin-2-amine, molecular formula is C9H13N3, molecular weight is 163.22, as common compound, the synthetic route is as follows.

To a stirred solution of (4,S)-7-(2-methylpyridin-4-yl)-2,3,4,5-tetrahydro-l,4- methanopyrido[2,3-£][l,4]diazepine (300 mg, 1.189 mmol in THF (30 mL) ) were added triethylamine (0.829 mL, 5.94 mmol) and triphosgene (353 mg, 1.189 mmol) under nitrogen, stirred at RT for 1 h. To this 4-(pyrrolidin-l-yl)pyridin-2-amine (388 mg, 2.378 mmol) was added and stirred at 70 C for 16 h. (TLC eluent: 10% MeOH in DCM, 1^:0.4, UV active). The reaction mixture was cooled to rt, partitioned between water and ethyl acetate (3X30 mL). The combined organic layer was washed with brine solution, dried over anhydrous Na2SC”4, filtered and filtrate was evaporated to get crude compound. The crude compound was purified by flash column chromatography (using neutral alumina and eluted at 20% EtOAc in pet ether) to afford the desired product (4,S)-7-(2-methylpyridin-4- yl)-N-(4-(pyrrolidin-l-yl)pyridin-2-yl)-3,4-dihydro-l,4-methanopyrido[2,3- £][l,4]diazepine-5(2H)-carboxamide (251 mg, 0.561 mmol, 47.2 % yield) as an off white solid. LCMS (m/z): 442.3 [M+H]+, Rt = 4.78 min.1H NMR (400 MHz, CDC13): delta 13.27 (s, 1 H), 8.60 (d, J = 5.3 Hz, 1 H), 8.28 (s, 1 H), 8.00 (d, J = 5.9 Hz, 1 H), 7.72 (dd, J = 5.5, 1.8 Hz, 1 H), 7.59 (d, J = 7.9 Hz, 1 H), 7.50 – 7.38 (m, 2 H), 6.19 (dd, J = 5.9, 2.3 Hz, 1 H), 5.70 (dd, J = 6.0, 3.2 Hz, 1 H), 3.39 (q, J = 6.2, 4.8 Hz, 3 H), 3.26 (s, 1 H), 3.27 – 3.12 (m, 3 H), 3.00 (dd, J = 12.0, 3.3 Hz, 1 H), 2.74 (s, 3 H), 2.32 (dddd, J = 14.0, 10.0, 6.2, 4.2 Hz, 1 H), 2.15 – 1.97 (m, 5 H).

Statistics shows that 722550-01-8 is playing an increasingly important role. we look forward to future research findings about 4-(Pyrrolidin-1-yl)pyridin-2-amine.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ELLIS, James Lamond; EVANS, Karen Anderson; FOX, Ryan Michael; MILLER, William Henry; SEEFELD, Mark Andrew; (766 pag.)WO2016/79709; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 56673-34-8 ,Some common heterocyclic compound, 56673-34-8, molecular formula is C5H4BrNS, 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.

5-Bromo-2-(cyclopropylmethylthio)pyridine To a solution of 5-bromopyridine-2-thiol (3.9 g) in THF (100 mL) was added NaH (1.24 g) at 0 C. and the mixture was stirred at 0 C. for 0.5 h. Then (bromomethyl)cyclopropane (2.79 g) was added. The mixture was allowed to warm to r.t. and stirred for 6 hours. The mixture was poured into ice water (200 mL) and extracted with EA (100 mL*3). The combined organic phases were washed with brine (50 mL) and then dried over Na2SO4. After filtration and evaporation of the solvent, the residue was purified by SGC (eluent: PE) to provide the subtitle compound. MS ESI+: m/z=244 [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. 56673-34-8, 3-Bromo-6-mercaptopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SANOFI; SCHWINK, Lothar; BOSSART, Martin; GLOMBIK, Heiner; GOSSEL, Matthias; KADEREIT, Dieter; KLABUNDE, Thomas; MAIER, Thomas; STENGELIN, Siegfried; US2014/99333; (2014); 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. 178421-21-1, name is Ethyl 6-chloro-5-methylpicolinate, the common compound, a new synthetic route is introduced below. Recommanded Product: 178421-21-1

Stage 1: (6-chloro-5-methylpyridin-2-yl)methanol 0.40 g of sodium borohydride (10.5 mmol) is added in portions to a solution of 1.20 g of 6-chloro-5-methylpyridine-2-carboxylic acid ethyl ester (6.00 mmol) and 10 ml of ethanol maintained at room temperature. The mixture is stirred for 4 hours and then the mixture is poured into an aqueous solution of sodium chloride and the mixture is extracted with ethyl acetate. The organic phase is dried over sodium sulfate, filtered and concentrated under vacuum. The title product is isolated by chromatography on a silica column (eluent: chloroform). 0.69 g of a colorless oil is recovered. Yield: 73% 1 H NMR (CDCl3) delta: 2.37 (s, 3H); 4.70 (s, 2H); 2.94 (s; broad); 7.17 (d, 1H); 7.55 (d, 1H)

The synthetic route of 178421-21-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pierre Fabre Medicament; US6020345; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 909717-95-9, name is Ethyl 4-methoxypyrazolo[1,5-a]pyridine-3-carboxylate, molecular formula is C11H12N2O3, 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. Application In Synthesis of Ethyl 4-methoxypyrazolo[1,5-a]pyridine-3-carboxylate

A mixture of the product from step 2 (500 mg, 126 rnmol) in 40% HBr (20 mL) was stirred at 120C for 16 hours. After cooling to RI, the mixture was concentrated in vacuo to give a residue, which was neutralized with saturated NaHCO3 aqueous solution to pH 7, extracted with the mixed solvent (DCM: iPropanol = 4: 1) (500 mL x 3). The organic layer was combined, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified bysilica chromatography (10% methanol in DCM) to give the title compound (290.0 mg) as yellow oil. LRMS mlz (M+H) 135,1 found, 135.1 required.

With the rapid development of chemical substances, we look forward to future research findings about 909717-95-9.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIVERTON, Nigel; KUDUK, Scott D.; BESHORE, Doug C.; MENG, Na; LUO, Yunfu; (127 pag.)WO2016/101119; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1092286-30-0 ,Some common heterocyclic compound, 1092286-30-0, molecular formula is C7H6ClNO2, 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.

5-Chloro-2-methyl-nicotinic acid (4.15 g, 24.2 mmol) is placed in a flask with DCM (100 mL) and oxalyl chloride (3.68 g, 29 mmol). DMF (200 muL) is added and the reaction mixture is stirred at r.t. for 1 hour (gas evolution). The mixture is filtered and the solvent is removed in vacuo to afford the title product which is used in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1092286-30-0, its application will become more common.

Reference:
Patent; Beattie, David; Colson, Anny-Odile; Culshaw, Andrew James; Sharp, Lisa; Stanley, Emily; Sviridenko, Lilya; US2010/35898; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem