Tag: M.W:100-200

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 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

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

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 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

Adding a certain compound to certain chemical reactions, such as: 7598-35-8, 2-Bromopyridin-4-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, HPLC of Formula: C5H5BrN2, blongs to pyridine-derivatives compound. HPLC of Formula: C5H5BrN2

To a cooled (0 C.) solution of 2,6-dichloro-4-iodobenzoyl chloride (70 mg, 0.21 mmol) in DMF (2 mL) was added NaH (17 mg, 0.42 mmol). The mixture was stirred for 10 minutes and then 2-bromopyridin-4-amine (40 mg, 0.23 mmol) was added. The resulting mixture was slowly warmed to 25 C., diluted with ethyl acetate (10 mL), quenched with water (1 mL), washed with saturated Na2CO3 and water, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by silica-gel chromatography (Pet Ether/EtOAc=20:1 to 3:1) to afford N-(2-bromopyridin-4-yl)-2,6-dichloro-4-iodobenzamide (40 mg, 40% yield). LCMS (ESI) m/z: 470.9 [M+H+].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7598-35-8, 2-Bromopyridin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; GENENTECH, INC.; US2010/317643; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 136888-21-6, 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. 136888-21-6, name is 2-Chloro-5-fluoro-3-nitropyridine, molecular formula is C5H2ClFN2O2, 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.

In a high-pressure reaction vessel, 2,3-dichloro-5-fluoropyridine 85g (0.5 mol) was added to 200 mL of ammonia water, and the temperature was set at 180 C., and the reaction under high pressure was performed for 24 h. The reaction of the starting material was complete by TLC, and the solvent was swirled to obtain 2- Chloro-5-fluoro-3-aminopyridine 65g;Place 2-chloro-5-fluoro-3-aminopyridine 65 g (0.45 mol) in a 900 mL round-bottomed flask in acetonitrile, and add 450 mL of water buffer solution (0.6 M K2CO3-4¡Á10-4 M EDTA disodium salt). 350 mL (3 mol) of acetonitrile and 290 mL (3 mol) of a 30% H2O2 aqueous solution, and the reaction mixture was stirred at room temperature for 1 hour and extracted with ethyl acetate (3 x 300 mL). The organic layers were combined and dried over anhydrous Na2SO4. The solvent was removed to give a sufficiently pure product, 2-chloro-5-fluoro-3-nitropyridine, 65 g;To a solution of 65 g (0.35 mol) of 2-chloro-5-fluoro-3-nitropyridine in DMSO/H2O (mass ratio 9:1, 3500 mL) was added L-proline 230 g (2 mol), Na2CO3 210 g (2 mol), NaN3 230 g (3.5 mol), sodium ascorbate 350 g (1.75 mol) and CuSO4.5H2O 500 g (2 mol); the mixture was stirred in an oil bath at 70C for 24 hours, and then the mixture was poured into 5000 mL of ice water to give a solid product. Filter and crystallize to obtain 47g of 2-amino-5-fluoro-3-nitropyridine; add 2-amino-5-fluoro-3-nitropyridine to the aqueous solution of sulfuric acid, add a certain amount of chloroacetic acid, and heat to 120C. After TLC monitored the reaction of the raw materials, the reaction mixture was extracted with methylene chloride. The pH of the organic phase was adjusted to 7-8 with a saturated sodium carbonate solution, and the organic phase was concentrated to obtain 2-amino-5-fluoro-pyridine.

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 136888-21-6, 2-Chloro-5-fluoro-3-nitropyridine.

Reference:
Patent; Henan Longhu Biological Co., Ltd.; Mu Kairui; Lei Yansheng; (13 pag.)CN107827887; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 69950-65-8 ,Some common heterocyclic compound, 69950-65-8, molecular formula is C8H7NO3, 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 3-bromo-2-phenyl-7-(trimethylsilyl)pyrazolo[1,5-a]pyridine (18, 550 mg, 1.59 mmol) in THF (4 mL) was added n-butyllithium (0.7 mL, 1.91 mmol, 2.6 mol/L solution in hexane) at -78 C. After stirring at -78 C for 0.5 h, a solution of methyl 6-formylpicolinate (527 mg, 3.19 mmol) in THF (4 mL) was added to the mixture at -78 C. The solution was stirred at room temperature for 1 h, and then the reaction was quenched by the addition of saturated aq. ammonium chloride. The mixture was extracted with ethyl acetate. The organic extracts were washed with brine, dried over sodium sulfate and concentrated in vacuo. The crude material was purified by flash column chromatography on silica gel (hexane:AcOEt = 4:1) to give the title compound 23 as a yellow oil (361 mg, 53%). 1H-NMR (400 MHz, CDCl3) delta 0.63 (9H, s), 4.21 (3H, s), 5.53 (1H, d, J = 2.4 Hz), 6.46 (1H, d, J = 2.4 Hz), 6.99 (1H, dd, J = 6.7, 1.8 Hz), 7.06 (1H, dd, J = 9.1, 6.7 Hz), 7.18 (1H, dd, J = 9.1, 1.8 Hz), 7.41-7.44 (2H, m), 7.62 (2H, tt, J = 7.3, 1.2 Hz), 7.86 (1H, t, J = 7.3 Hz), 8.03-8.07 (2H, m), 8.18 (1H, d, J = 7.3 Hz). IR (ATR) nmax 3417, 2953, 2898, 1720, 1586, 1516, 1439, 1356, 1314, 1243, 1138, 1079, 1029, 992, 892, 833, 759, 706, 634, 582, 506, 419 cm-1. MS (ESI) 432 [M+H]+. HRMS (ESI) calcd for C24H26N3O3Si [M+H]+ 432.17434, found 432.17514.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,69950-65-8, its application will become more common.

Reference:
Article; Nishigaya, Yosuke; Umei, Kentaro; Saito, Yoshifumi; Watanabe, Hiroyuki; Kondo, Tatsuhiro; Kondo, Atsushi; Kawamura, Naohiro; Tatani, Kazuya; Kohno, Yasushi; Tanaka, Nobuyuki; Seto, Shigeki; Bioorganic and Medicinal Chemistry Letters; vol. 27; 17; (2017); p. 4044 – 4050;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 53014-84-9, 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 53014-84-9, name is 2-Methyl-5-formylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

A solution containing the product from Example 6F (0.150 g, 0.65 mmol) in a mixture of toluene (2.5 mL) and methanol (2.5 mL) was treated with the product from Example 13A (0.079 mL, 0.65 mmol), stirred at 50 C. for 16 hours, cooled to 25 C., treated with sodium borohydride (0.049 g, 1.29 mmol), stirred at 25 C. for 1 hour, quenched with 1N NaHCO3 and stirred for 1 hour, and partitioned between ethyl acetate and water. The organic phase was washed with brine and dried over MgSO4, filtered and concentrated. A solution of the concentrate (0.194 g) in 1,2-dichloroethane (10 mL) was treated with N,N-disuccinimidyl carbonate (0.20 g, 0.781 mmol) and triethylamine (0.11 mL, 0.789 mmol), stirred at 25 C. for 16 hours, and partitioned with 10% Na2CO3. The aqueous was extracted with additional chloroform. The combined organic phase was dried over MgSO4, filtered and concentrated. A solution of the concentrate (0.223 g) in dichloromethane (2.5 mL) was treated with trifluoracetic acid (2.5 mL), and the mixture was stirred at 25 C. for 2 hours. The solvent was concentrated to give the title compound (0.379 g) as the trifluoroacetic acid salt, which was used without further purification.

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 53014-84-9, 2-Methyl-5-formylpyridine.

Reference:
Patent; DeGoey, David A.; Flentge, Charles A.; Flosi, William J.; Grampovnik, David J.; Kempf, Dale J.; Klein, Larry L.; US2005/131017; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 73583-37-6 , The common heterocyclic compound, 73583-37-6, name is 4-Bromo-2-chloropyridine, molecular formula is C5H3BrClN, 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.

n-Butyllithium (7.8 mL of a 1.6 M solution with hexanes, 12 mmol) was added to a stirring solution of 4-bromo-2-chloropyridine (1.2 mL, 10 mmol, Alfa Aesar, Ward Hill, MA) and diethyl ether (52 mL) at -78 C. After 30 min, cyclobutanone (3.9 mL, 52 mmol) and water (50 mL) were added sequentially, and then the reaction mixture was warmed to room temperature, partitioned between ethyl acetate and more water, and the layers were separated. The organic material was dried (magnesium sulfate), silica gel (2.0 g) was added, and the volatiles were removed under a vacuum. The residue was subjected to flash chromatography on silica gel (40 g RediSep normal phase column, gradient elution of 0% to 30% ethyl acetate-hexane, Teledyne Isco, Lincoln, NE) to afford l-(2-chloro-4-pyridinyl)cyclobutanol (1.6 g).

The synthetic route of 73583-37-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; ASHTON, Kate; BARTBERGER, Michael D.; BOURBEAU, Matthew Paul; CROGHAN, Michael D.; FOTSCH, Christopher H.; HUNGATE, Randall W.; KONG, Ke; NISHIMURA, Nobuko; NORMAN, Mark H.; PENNINGTON, Lewis D.; REICHELT, Andreas; SIEGMUND, Aaron C.; TADESSE, Seifu; ST. JEAN, David Jr; YANG, Kevin C.; YAO, Guomin; WO2013/173382; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem