Category: pyridine-derivatives

Synthetic Route of 122851-69-8, 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. 122851-69-8, name is 3-Bromo-2-(chloromethyl)pyridine. A new synthetic method of this compound is introduced below.

A solution of cis-4-(2,3,6-trifluorophenyl)cyclohexanol (3.66 g) in THF (100 ml)was cooled to 0C, 60% sodium hydride (1.272 g) was added, and the mixture wasstirred under a calcium chloride tube dry atmosphere at room temperature for 10 min.To the reaction mixture was added 3-bromo-2-(chloromethyl)pyridine (4.92 g), and themixture was stirred at 70C for 3 hr. Water was added to the mixture at room temperature,and the mixture was extracted with ethyl acetate. The organic layer waswashed with saturated brine, dried over anhydrous sodium sulfate, and the solvent wasevaporated under reduced pressure. The residue was purified by silica gel chromatography(ethyl acetate/hexane) to give the title compound (3.73 g).MS, found: 401.0,403.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,122851-69-8, 3-Bromo-2-(chloromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; FUJIMOTO Tatsuhiko; RIKIMARU Kentaro; FUKUDA Koichiro; SUGIMOTO Hiromichi; MATSUMOTO Takahiro; TOKUNAGA Norihito; HIROZANE Mariko; (166 pag.)WO2017/135306; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 920979-05-1, Adding some certain compound to certain chemical reactions, such as: 920979-05-1, name is 5-(Trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid,molecular formula is C9H5F3N2O2, 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 920979-05-1.

10.3 5-(Trifluoromethyl)pyrrolo[3,2-b]pyridine-2-ethyl carboxylate; 1 mL (18.71 mmol) of concentrated sulfuric acid is added to a solution of 0.2 g (0.87 mmol) of 5-trifluoromethyl-pyrrolo[3,2-b]pyridine-2-carboxylic acid, obtained in Stage 10.2, in 10 mL of ethanol. It is stirred under reflux for 20 hours then the solution is cooled, and concentrated at reduced pressure. The resultant residue is then taken up in 50 mL of dichloromethane then washed successively with 20 mL of a saturated aqueous solution of sodium bicarbonate, 40 mL of water and 20 mL of saturated aqueous solution of sodium chloride, dried over sodium sulfate and then concentrated at reduced pressure. We obtain 0.19 g of product, which is used as it is in the next stage.

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. 920979-05-1, 5-(Trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SANOFI-AVENTIS; US2010/41634; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 120739-77-7, 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. 120739-77-7, name is N-((6-Chloropyridin-3-yl)methyl)ethanamine, molecular formula is C8H11ClN2, 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.

352.0 g of n-butyl acetate and 102.9 g of a 35% potassium carbonate aqueous solution were charged in a 1-L separable flask. The solution was cooled to 4C, 48.8 g of 1,1-dichloro-2-nitroethene (net weight 40.6 g) was added dropwise while stirring over 30 minutes, and 44.8 g of 2-chloro-5-(ethylaminomethyl)pyridine (net weight 44.4 g) was subsequently added dropwise over 3 hours. The reaction mixture was stirred at -4C for 15 minutes, 60.6 g of a 40% methyl amine solution was added dropwise over 3 hours, and the stirring was further continued for 4 hours. The obtained reaction mixture was warmed to 15C and extracted four times with 51.5 g, 40.3 g, 30.0 g, and 30.0 g of water, and the obtained four extracted aqueous layers were combined. The combined aqueous layer was extracted four times with 75.0 g of 5-ethyl-2-methylpiridine at 15C, and the obtained four extracted 5-ethyl-2-methylpyridine layers were combined (amount of the recovered aqueous layer 1, 247.8 g). After washing the combined 5-ethyl-2-methylpyridine layer with 50.0 g of a saturated sodium sulfate solution (amount of the recovered aqueous layer 2, 66.0 g), 800 g of n-heptane was added thereto and concentrated at 4.5 kPa, 25 to 35C until the amount of the residual solution was 345 g. 20.0 g of 5-ethyl-2-methylpyridine was added to the concentrated mass, and the mixture was maintained at 40C for 1 hour followed by filtration to remove insoluble matters. The obtained filtrate was flushed down with 10.0 g of 5-ethyl-2-methylpyridine to a 500-ml separable flask, the temperature was adjusted to 35C. Then 0.01 g of seed crystals of (1E)-N-[(6-chloro-3-pyridinyl)methyl]-N-ethyl-N’-methyl-2-nitro-1,1-ethenediamine was added and the mixture was cooled to 15C over 5 hours, and subsequently cooled at -10C over 10 hours for crystallization. The crystalline mass was further stirred at -10C for 3 hours and filtered (recovered filtrate amount, 304.1 g). The obtained crystals were washed with 300.0 g of n-butyl acetate which had been cooled to -10C (recovered washing amount, 305.9 g). The washed crystals were dried at 2.7 kPa, 40C for 4 hours to obtain 45.3 g of (1E)-N-[(6-chloro-3-pyridinyl)methyl]-N-ethyl-N’-methyl-2-nitro-1,1-ethenediamine at a content of 98.9%

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 120739-77-7, N-((6-Chloropyridin-3-yl)methyl)ethanamine.

Reference:
Patent; Sumitomo Chemical Company, Limited; EP2186802; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 89364-04-5, 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.89364-04-5, name is 3-Bromo-4-nitropyridine, molecular formula is C5H3BrN2O2, molecular weight is 202.9935, as common compound, the synthetic route is as follows.

Under a nitrogen atmosphere, was added 0.05mol A-1,0.06mol raw material B-1, was added a mixed solvent (180ml THF to a three-necked flask of 500ml, 90ml H2O) was dissolved, nitrogen was stirred for 1 hour and then added 0.1mol K2CO3, 0.0005mol Pd (PPh3)4And heated to 80 , 20 hours, the reaction was observed by thin layer chromatography (TLC), until the reaction was complete.After cooling to room temperature, extracted with methylene chloride was added to the reaction system, liquid separation, the organic phase was spin evaporated under reduced pressure until no fraction.The resulting material was purified by silica gel column, to give the intermediate C-1.

The chemical industry reduces the impact on the environment during synthesis 89364-04-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Jiangsu March Optoelectric Technology Co., Ltd.; Li Chong; Chen Haifeng; Zhang Zhaochao; Xu Haojie; (47 pag.)CN110372715; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 86521-05-3, 2-((Trimethylsilyl)ethynyl)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, Safety of 2-((Trimethylsilyl)ethynyl)pyridine, blongs to pyridine-derivatives compound. Safety of 2-((Trimethylsilyl)ethynyl)pyridine

2-Ethynyl-pyridineA solution of 2-trimethylsilanylethynyl-pyridine (3.05 g, 14 mmol) in MeOH (8.5 mL) was added dropwise to potassium hydroxide solution (1 N, 14 mL) and the reaction mixture was stirred at room temperature for 1 h and then acidified with HC1 (3 N, 8.5 mL) and the mixture concentrated. The residue was then diluted with water and make alkaline with solid sodium carbonate, extracted with diethyl ether and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, diethylether) afforded the title compound (1.3 g, 75%) as a brown liquid. MS: m/e = 176.0[M+H]+.

The synthetic route of 86521-05-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HERNANDEZ, Maria-Clemencia; LUCAS, Matthew C.; THOMAS, Andrew; WO2012/62687; (2012); 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 183483-29-6, name is 2-(2-Bromopyridin-4-yl)acetic acid. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 2-(2-Bromopyridin-4-yl)acetic acid

To a solution of 2-(2-bromo-4-pyridyl)acetic acid (300 mg, 1.39 mmol), diisopropylethylamine (538 mg, 4.17 mmol) and HATU (634 mg, 1.67 mmol) in DCM (15 mL) was added ethyl 2-amino-2-methyl-propanoate (256 mg, 1.53 mmol, HCl salt) and the reaction mixture was stirred at 20 C for 16 hours. On completion, the reaction mixture was concentrated in vacuo. The residue was purified by silica gel chromatography (petroleum ether:ethyl acetate = 1:1) to give the title compound (430 mg, 94% yield) as a light yellow solid. LCMS: (ES+) m/z (M+H)+= 329.0, tR = 0.679.1H NMR (400MHz, CDCl3) delta = 8.33 (d, J = 5.2 Hz, 1H), 7.45 (d, J = 1.2 Hz, 1H), 7.22 (dd, J = 1.2, 5.2 Hz, 1H), 6.27 (br. s., 1H), 4.20 (q, J = 7.2 Hz, 2H), 3.49 (s, 2H), 1.57 (s, 6H), 1.26 (t, J = 7.2 Hz, 3H)

With the rapid development of chemical substances, we look forward to future research findings about 183483-29-6.

Reference:
Patent; RAZE THERAPEUTICS, INC.; MAINOLFI, Nello; (215 pag.)WO2018/106636; (2018); 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. 131747-62-1, name is 3-(Trifluoromethyl)pyridine-2-carboxaldehyde, the common compound, a new synthetic route is introduced below. Safety of 3-(Trifluoromethyl)pyridine-2-carboxaldehyde

N-((6- Azaspiro[2.5]octan-l-yi)methyl)-6-(2-chioro-5-fluorophenyi)pyridazm-3-aniine hydrochloride salt (11 mg, 0.028 mmol) was suspended in DCM (1 raL) and 3-(trifluoromethyl)pyridine-2- carbaldehyde (24 mg, 0.14 mmol) was added and allowed to stir at r.t. for 5 min, after which time sodium triacetoxyborohydride (30 mg, 0.14 mmol) was added. The resulting solution was stirred at r.t. overnight, after which time the reaction mixture was quenched with sat. NaHCO-j, and extracted with 3: 1 chloroform/IP A. Organic extracts were filtered through a phase separator, and concentrated. Crude residue was purified by RP-HPLC, and fractions containing product were basified with sat. NaHCQs, and extracted with 3: 1 chloroform/IP A. Organic extracts were filtered through a phase separator and concentrated to give the title compound as a colorless oil (6.2 mg, 44%). -WJR (400 MHz, CDCI3) delta 8.80 (dd, J= 4.6, 0.8 Hz, 1H), 7.95 (dd, J = 8.0, 1.2 Hz, 1H), 7,61 (d, ./ 9.3 Hz, I I I). 7,48 (dd, J = 9:2, 3, 1 Hz, 1H), 7,41 (dd, ,/ 8.8, 5,0 Hz, 1 1 1). 7.31 (dd, J= 7.8, 4.8 Hz, 1H), 7,07 – 7.02 (m, 1 1 1). 6.68 (d, J= 9.3 Hz, H i). 4.83 (t, ./ 4.6 Hz, 1H), 3,83 (s, 2H), 3,52 – 3.41 (m, 2H), 2,67 – 2.62 (m, 2H), 2.50 – 2,45 (m, 21 1). 1.83 – 1,78 (m, 1H), 1,69 – 1.65 (m, I I I). 1 ,49 – 1 ,46 (m, 1 1 1). 1.25 – 1 ,20 (m, H i). 1.05 – 0,97 (m, IH), 0.61 (dd, J= 8.4, 4.6 Hz, IH), 0,28 (t, ,/ 4,9 Hz, H i), ES-MS [M+H]+ = 506.2,

The synthetic route of 131747-62-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VANDERBILT UNIVERSITY; LINDSLEY, Craig, W.; BRIDGES, Thomas, M.; CONN, P., Jeffrey; BENDER, Aaron, M.; ENGERS, Darren, W.; (130 pag.)WO2019/14427; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 65873-72-5, 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. 65873-72-5, name is 6-Methoxynicotinaldehyde, molecular formula is C7H7NO2, 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 25 : 1-(3,4-Difluorobenzyl)-5-(phenoxymethyl)pyridin-2(1H)-one (Final Compound 16-03) ;Step 1 : (6-Methoxypyridin-3-yl)methanol According to Scheme 16 Method A: A solution of 6-methoxynicotinaldehyde (leq, 2.19mmol, 0.30g) and LiAlH4 (0.5eq, 1.05mmol, 0.04g) in THF (10mL) was stirred for 30 min. at 0C and overnight at room temperature. After the addition of AcOEt, the reaction mixture was diluted with water. The organic layer was washed with saturated NH4Cl solution, dried over Na2SO4, filtered and evaporated. The resulting crude residue was purified by silica gel chromatography (AIT Flashsmart prepacked column 25g SiO2) using CH2Cl2/AcOEt 80/20 to afford (6-methoxypyridin-3-yl)methanol (1.80mmol, 0.26g, 90%) as a pale oil. LC (XTerra RP18, 3.5mum, 3.0x50mm Column): RT = 1.86min; MS m/z (CI) [MH]+= 140.

According to the analysis of related databases, 65873-72-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; ADDEX PHARMACEUTICALS S.A.; WO2006/30032; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1018505-59-3 , The common heterocyclic compound, 1018505-59-3, name is 5-(4-Ethylpiperazin-1-yl)pyridin-2-amine, molecular formula is C11H18N4, 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.

The 4 – (2 – chloro -3 – fluoro – pyrazine amino) -2 – pyrimidine formic acid (1.35 g 1.2 eq), 5 – (4 – ethyl – piperazine -1 – yl) – piperidine -2 – amino (0.81 g 1 eq) and triethylamine (500 mul) in DMF (15 ml) in, then added HBTU (1.51 g 1.5 eq). The mixture stirring at room temperature to 16 hours, then EtOAc (50 ml) and saturated NaHCO3Solution (15 ml), and for separating each layer of EtOAc (2 × 15 ml) extraction the aqueous layer, the combined organic layer dried (MgSO4), filtering and evaporation to dryness, the residue through the column chromatography purification, and to obtain white solid compound of 1.42 g (yield: 62%).

The synthetic route of 1018505-59-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangxi Runze Pharmaceutical Co., Ltd.; Liao Niansheng; Zou Mingming; Hu Xiande; Sui Rongchun; Xu Man; (14 pag.)CN108689997; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 886365-06-6, 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 886365-06-6, name is Methyl 5-bromo-4-methylpicolinate. This compound has unique chemical properties. The synthetic route is as follows.

5-Bromo-4-methyl-pyridine-2-carboxylic acid methylamide 5-Bromo-4-methyl-pyridine-2-carboxylic acid methylamide: To 5-Bromo-4-methyl-pyridine-2-carboxylic acid methyl ester (200 mg, 0.869 mmol) and methylamine (135 mg, 11.34 mmol) was added (CH3)3Al (0.6 mg, 0.008 mmol). The mixture was placed in a sealed tube and heated at 100 C. for 1 h, after which the mixture was cooled, quenched with water, and extracted with EtOAc. The organic phase was dried, concentrated, and purified by column chromatograph to give 5-Bromo-4-methyl-pyridine-2-carboxylic acid methylamide (130 mg, 65%) as an off-white solid.

According to the analysis of related databases, 886365-06-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Alam, Muzaffar; Du Bois, Daisy Joe; Hawley, Ronald Charles; Kennedy-Smith, Joshua; Minatti, Ana Elena; Palmer, Wylie Solang; Silva, Tania; Wilhelm, Robert Stephen; US2011/71150; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem