Month: April 2022

Adding a certain compound to certain chemical reactions, such as: 75893-75-3, 6-Cyclopropylnicotinic acid, 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, 75893-75-3, blongs to pyridine-derivatives compound. Formula: C9H9NO2

Step-6: Synthesis of N-[3-bromo-2-[[tert-butyI(dimethyl)siIyl]oxymethyl]phenyl]-6- cyclopropyl-pyridine-3-carboxamide: To a solution of 6-cyclopropylpyridine-3-carboxylic acid (0.5 g, 3.06 mmol), 3-bromo-2-[[tert- butyl(dimethyl)silyl]oxymethyl]aniline (1.16 g, 3.67 mmol) and HOBt (0.495 g, 3.67 mmol) in DCM (15 mL) was added NMM (0.5 mL, 4-59 mmol) and EDCI.HCl (0.876 g, 4.59 mmol). The reaction mixture was stirred at room temperature for 16 h. After completion of the reaction (as indicated by TLC), water (10 mL) was added to it and extraction was carried out using DCM (50 mL x 2). The combined organic layers were washed with brine (50 mL), dried over anhydrous Na2S04, filtered and concentrated under reduced pressure. The residue was purified using column chromatography (Si02, 10% ethyl acetate in hexanes) to afford title compound (0.5 g, 35%). LCMS: m/z 461.2 (M + 1)+. NMR (400 MHz, CDC13) delta 0.15 (s, 6H), 0.87 (s, 9H), 1.05-1.10 (m, 2H), 1.1 1-1.51 (m, 2H), 2.06-2.16 (m, 1H), 5.1 1 (s, 2H), 7.19-7.23 (aromatics, 2H), 7.33 (d, J = 8.0 Hz, 1H), 8.03 (dd, J = 8.0, 2.0 Hz, 1H), 8.33 (d, J = 8.0 Hz, 1H), 8.99 (d, J = 2.0 Hz, lH), 9.99 (s, lH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,75893-75-3, its application will become more common.

Reference:
Patent; ADVINUS THERAPEUTICS LIMITED; THAKKAR, Mahesh; KOUL, Summon; BHUNIYA, Debnath; SINGH, Umesh; WO2013/157021; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 372198-69-1, 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 372198-69-1, name is Ethyl 6-bromoimidazo[1,2-a]pyridine-3-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of ethyl 6-bromoimidazo[l,2-a]pyridine-3-carboxylate (180 mg, 0.67 mmol) THF (2 mL) and methanol (2 mL) was added LiOH (56 mg 1.34 mmol) in water (2 mL) and stirred at 60 C overnight. After removal of volatile solvent by rotary evaporation, the mixture was diluted with water and acidified to pH 4 with an aqueous solution of IN HC1. The resulting precipitate was collected by filtration, washed with water, and dried under vacuum to afford the title compound (108 mg, 67%). This intermediate was used in subsequent reactions without further purification. LC-MS: single peak at 254 nm, MH+ calcd. for C8H6BrN202: 241, obtained: 241.

According to the analysis of related databases, 372198-69-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FENG, Yangbo; CHEN, Yen Ting; SESSIONS, Hampton; MISHRA, Jitendra K.; CHOWDHURY, Sarwat; YIN, Yan; LOGRASSO, Philip; LUO, Jun-Li; BANNISTER, Thomas; SCHROETER, Thomas; WO2011/50245; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1092286-30-0, 5-Chloro-2-methyl-3-pyridinecarboxylic acid, 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: 1092286-30-0, blongs to pyridine-derivatives compound. Recommanded Product: 1092286-30-0

5-Chloro-2-methylnicotinoyl chloride5-Chloro-2-methyl-nicotinic acid (4.15 g, 24.2 mmol) was placed in a flask with DCM (100 ml) and oxalyl chloride (3.68 g, 29 mmol). DMF (200muIota) was added and the reaction mixture was stirred at RT for 1 hour (gas evolution). The mixture was filtered and the solvent was removed in vacuo to afford the title product which was used without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1092286-30-0, 5-Chloro-2-methyl-3-pyridinecarboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; BEATTIE, David; BRUCE, Ian; COLSON, Anny-Odile; CULSHAW, Andrew James; SHARP, Thomas; WO2011/95450; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 72093-04-0, 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. 72093-04-0, name is 3-Chloro-4-methylpyridine. A new synthetic method of this compound is introduced below.

EXAMPLE 32 Compound CM A solution of diisopropylamine (1.23 mL) in dry tetrahydrofuran (15 mL) is stirred and cooled to -70 C. under a nitrogen atmosphere. To this is added a 2.5M solution of n-butyl lithium in hexanes (3.52 mL) at -70 C. The mixture is stirred for 30 minutes then a solution of 3-chloro-4-methylpyridine (1.02 g) in dry tetrahydrofuran (10 mL) is added. The mixture is stirred for a further 40 minutes. A solution of 3-cyclopentyloxy-4,N-dimethoxy-N-methylbenzamide (2.23 g) in dry tetrahydrofuran (10 mL) is added and the mixture stirred at -70 C. for 30 minutes, -40 C. for 30 minutes, 0 C. for 30 minutes, and room temperature for 1 hour. A mixture of ethanol and hydrochloric acid 19:1 (40 mL) is added and then the reaction mixture is partitioned between brine (40 mL) and diethyl ether (40 mL). The ethereal phase is dried over sodium sulfate and concentrated in vacuo to give a pale yellow solid (3.0 g). The solid is triturated with diethyl ether and then purified by flash chromatography (ethyl acetate eluent on a silica column) to give a solid (1.6 g). The solid is triturated with diethyl ether, collected and dried to afford 1-(3-cyclopentyloxy-4-methoxyphenyl)-2-(3-chloropyrid-4-yl)ethanone (1.35 g) as a cream solid m.p. 124-125 C. ?Elemental analysis: C,66.2; H,5.89; N,4.12%; calculated for C19 H20 ClNO3: C,65.99; H,5.83;[N,4.05%.]

At the same time, in my other blogs, there are other synthetic methods of this type of compound,72093-04-0, 3-Chloro-4-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; Rhone-Poulenc Rorer Limited; US5935978; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1030632-94-0, 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. 1030632-94-0, name is 5-Ethyl-2-(trifluoromethyl)pyridine, molecular formula is C8H8F3N, 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.

Step 3. Preparation of 5-(1-Bromoethyl)-2-trifluoromethylpyridine N-Bromosuccinimide (1.78 g, 0.01 mol) was added to anhydrous fresh methylene chloride (60 mL) at room temperature under an atmosphere of nitrogen. Once dissolved, the solution was cooled to 0 C. The 5-ethyl-2-trifluoromethyl-pyridine pyridine (1.75 g, 0.01 mol) was dissolved in a small amount of anhydrous methylene chloride and was added via syringe followed by zirconium tetrachloride (117 mg, 0.5 mmol). The ice bath was taken away and the mixture allowed to stir at room temperature overnight. TLC showed complete reaction (9:1, hexane:EtOAc). The reaction mixture was quenched with saturated sodium bicarbonate (25 mL). The organic layer was separated and washed with brine and dried (MgSO4). The residue was purified by column chromatography (1:20, EtOAc:Hex) to give the product, 2.04 g (80%), as a pale yellow liquid; 1H NMR (CDCl3) delta 8.77 (s, 1H), 7.97 (d, 1H), 7.69 (d, 1H), 5.21 (q, 1H), 2.08 (d, 3H)

According to the analysis of related databases, 1030632-94-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Heller, Stephen T.; Ross, Ronald; Irvine, Nicholas M.; Renga, James M.; Zettler, Mark M.; Erndt, Kim E.; US2008/132705; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 130473-26-6, 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 130473-26-6 as follows.

C174 (500 mg, 3.42 mmol) is dissolved in 1.5 mL formic acid. The solution is cooled in an ice bath, 30% aqueous hydrogen peroxide (722 muL, 6.8 mmol) is added drop-wise, and the reaction is stirred 1 h in an ice bath, and allowed to stand overnight at 5 C. The mixture is diluted with H2O, the solid is collected, washed with H2O and is dried to give 522 mg of an off-white solid. The formate salt is added to 7 mL H2O, 3 mL 2N NaOH is added, and the pH is adjusted to 3 with 5% aqueous HCl. The precipitate is collected and is dried to afford 1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid (C176) (67% yield). HRMS (FAB) calculated for C8H6N2O2+H: 163.0508, found 163.0507 (M+H). Example 23(i) can be obtained by coupling either exo-[2.2.1]-3-Amine or endo-[2.2.1]-3-Amine with C176.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,130473-26-6, its application will become more common.

Reference:
Patent; Walker, Daniel Patrick; Piotrowski, David W.; Jacobsen, Eric Jon; Acker, Brad A.; Wishka, Donn G.; Reitz, Steven Charles; Groppi JR., Vincent E.; US2003/153595; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 23628-31-1 , The common heterocyclic compound, 23628-31-1, name is 6-Aminopicolinic acid, molecular formula is C6H6N2O2, 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 solution of 2-amino-6-pyridinecarboxylic acid (6.0 g, 43.5 mmol) in ethanol (150 mL) was added thionyl chloride (12.0 g, 101 mmol) at 0 C. The resulting reaction mixture was stirred at reflux for 12 h. Upon cooling to room temp, the reaction mixture was concentrated under reduced pressure. Saturated aqueous Na2CO3 solution was added until the pH of the solution reached 9. The mixture was concentrated under reduced pressure and dichloromethane (150 mL) was added to the resulting residue. The mixture was stirred vigorously at room temp for 30 min and then filtered. The filtrate was concentrated under reduced pressure to afford ethyl 6-aminopicolinate (5.5 g, 76 % yield)

The synthetic route of 23628-31-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; CASAUBON, Rebecca, L.; NARAYAN, Radha; OALMANN, Christopher; VU, Chi, B.; WO2013/59587; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 18699-87-1, 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. 18699-87-1, name is 2-Methyl-3-nitropyridine. A new synthetic method of this compound is introduced below.

EXAMPLE 2; 3-{4-[3-(2-Fluoro-5-trifluoromethylphenyl)-ureido]phenyl}-1H-pyrrolo[3,2-b]pyridine-2-carboxamide; Method b:; Ethyl 3-(3-nitropyridin-2-yl)-2-oxopropionate 121.7 g of ethyl oxalate and then 15.8 g of 2-methyl-3-nitropyridine in solution in 100 ml of ethanol are added to a solution of sodium ethanolate, prepared by adding 4 g of sodium to 400 ml of ethanol stirred under argon. The reaction mixture is stirred for 15 hours and the solid formed is filtered off, washed successively with 100 ml of ethanol and 100 ml of diisopropyl ether, and then filter-dried. The solid is taken up in 300 ml of ethanol and acidified with a 5N hydrochloric acid solution. The solid obtained is filtered off, washed with 50 ml of a 5N hydrochloric acid solution and then with 100 ml of ethanol, and filter-dried. After drying under vacuum, 18.7 g of ethyl 3-(3-nitro yridine-2-yl)-2-oxopropionate are obtained, the characteristics of which are as follows: MS (ES+) spectrum: m/z=239 [MH]+Melting point=38 C. (Koefler bench). 1H NMR spectrum (400 MHz, DMSO-d6, delta in ppm): 1.30 (t, J=7.0 Hz, 3H); 4.29 (q, J=7.0 Hz, 2H); 7.12 (s, 1H); 7.57 (dd, J=5.5 and 8.5 Hz, 1H); 8.66 (broad d, J=8.5 Hz, 1H); 8.85 (broad d, J=5.5 Hz, 1H); 14.9 (broad m, 1H). IR spectrum (KBr): 1722; 1644; 1560; 1532; 1346; 1231; 1141; 1024 and 777 cm-1

At the same time, in my other blogs, there are other synthetic methods of this type of compound,18699-87-1, 2-Methyl-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; AVENTIS PHARMA S.A.; US2007/259910; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 18513-79-6, 1,2,3,6-Tetrahydropyridine hydrochloride, 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, Computed Properties of C5H10ClN, blongs to pyridine-derivatives compound. Computed Properties of C5H10ClN

The foregoing 3-oxide can also be obtained as follows: 40 g. of 1,2,5,6-tetrahydropyridine hydrochloride and 30 g. of sodium dicyanamide are suspended in 400 ml. of n-butanol and 30 ml. of water and heated to reflux overnight. The mixture is cooled and filtered and the filtrate is evaporated. The residue is digested in 100 ml. of water and the solid substance is filtered off and recrystallized from o-xylene, there being obtained pure 1-(1,2,5,6-tetrahydropyridine)-3-cyanoguanidine having a melting point of 131-133 C.

The synthetic route of 18513-79-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-La Roche Inc.; US4276417; (1981); A;,
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. 77145-64-3, name is 2-Chloro-6-(methylthio)pyridine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C6H6ClNS

(Example 15) 2-chloro-6-methylthiopyridine (1.00 g, 6.26 mmol) and succinimide (62 mg, 0.63 mmol) were mixed with toluene (20 mL). 10% aqueous solution of sodium hypochlorite (11.6 g, 15.7 mmol) was added dropwise to the mixture at 0 to 5C, and it was stirred for 1 hour. After that, ethyl acetate (10 mL), water (10 mL) and sodium sulfite (473 mg, 3.76 mmol) were added to the mixture, and it was stirred. After stirring and separation, an organic layer was concentrated under reduced pressure, and the residue was subjected to purification by means of a silica gel column to obtain 2-chloro-6-methylsulfonylpyridine (1.18 g, yield: 98%). 1H-NMR (300MHz, CDCl3) delta 3.26 (3H, s), 7.57-7.60 (1H, m), 7.90-8.05 (2H, m)

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, 77145-64-3, 2-Chloro-6-(methylthio)pyridine.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2003116; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem