Tag: M.W:100-200

Adding a certain compound to certain chemical reactions, such as: 88312-64-5, Methyl 2-amino-5-nitronicotinate, 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 Methyl 2-amino-5-nitronicotinate, blongs to pyridine-derivatives compound. Safety of Methyl 2-amino-5-nitronicotinate

DMAP (0.744 g, 6.09 mmol, 0.1 equiv) and Boc2O (29.2 g,134 mmol, 2.2 equiv) were successively added portionwise toa suspension of 22 (12.0 g, 60.9 mmol) in freshly distilled THF (200 mL) at room temperature. The solution was stirred at room temperature for 4 h and evaporated in vacuo. The crude product was purified by flash chromatography using PE/DCM/Et3N (86:13:1,v/v/v) to give 23 (22.5 g, 93%) as a colourless solid

At the same time, in my other blogs, there are other synthetic methods of this type of compound,88312-64-5, Methyl 2-amino-5-nitronicotinate, and friends who are interested can also refer to it.

Reference:
Article; Hedou, Damien; Deau, Emmanuel; Harari, Marine; Sanselme, Morgane; Fruit, Corinne; Besson, Thierry; Tetrahedron; vol. 70; 35; (2014); p. 5541 – 5549;,
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 72716-80-4, name is 5,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 5,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

To a suspension of 5,6-dimethyl-2-oxo-l,2-dihydropyridine-3-carbonitrile (5.90 g) in Eta2O(145 ?iL) was added cone. HCl (145 mL) dropwise and the mixture was stirred at ambient temperature for 15 min and at reflux for 60.5 h and concentrated under reduced pressure. The residue was suspended with CHCl3 (150 mL) and MeOH (7.5 mL) and the mixture was heated at 65 0C on a water bath and filtered. The insoluble material was suspended in CHCl3 (100 mL) and MeOH (5 mL) and the mixture was heated at 65 0C on a water bath and filtered. The combined filtrate was concentrated under reduced pressure. To the residue were added MeOH (75 mL) and K2CO3 (5 g) and the mixture was stirred at ambient temperature for 30 min. The insoluble material was filtered and the filtrate was concentrated under reduced pressure. The residue was dissolved in CHCl3 (100 mL) and the insoluble material was filtered. The filtrate was concentrated under reduced pressure to give 5,6- dimethylpyridin-2(lH)-one (2.19 g) as a yellow solid.1HNMR (300 MHz, CDCl3, delta): 2.05 (s, 3H), 2.31 (s, 3H), 6.38 (d, J= 9.2 Hz, IH), 7.26 (d, J= 9.2Hz, IH); ESI MS m/z 124 (M+H-I, 100%).

With the rapid development of chemical substances, we look forward to future research findings about 72716-80-4.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; ARENA PHARMACEUTICALS, INC.; WO2006/35967; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.52605-96-6, name is 2-Chloro-3-methoxypyridine, molecular formula is C6H6ClNO, molecular weight is 143.57, as common compound, the synthetic route is as follows.Computed Properties of C6H6ClNO

A three-necked flask was charged with Compound 1 (5.58 g, 39.0 mmol), N, N-dimethylformamide (60 mL) and sodium methoxide (6.20 g, 115.0 mmol); the reaction was stirred overnight at 60 C.The reaction was cooled to room temperature, water (120 mL) was added and extracted with ethyl acetate (80 mL x 3); the organic phases were combined, washed with water (100 mL x 2) and saturated brine (100 mL), dried over sodium sulfate, . The filtrate was spin-dried to give a yellow liquid, compound 2 (4.0 g, 28.9 mmol, 74%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,52605-96-6, 2-Chloro-3-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; Kanghua (Shanghai) Drug Discovery Co., Ltd.; Ma Jingxiang; (5 pag.)CN107286084; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.76005-99-7, name is 2-Methoxy-4-methylpyridin-3-amine, molecular formula is C7H10N2O, molecular weight is 138.1671, as common compound, the synthetic route is as follows.Recommanded Product: 2-Methoxy-4-methylpyridin-3-amine

(2) 29.4 g of Compound 2 was dissolved in 600 mL of DCM in a 2 L three-necked flask, and 25.0 g of AcOK potassium acetate was added at 0 C., and 43.4 g of Ac2O; about 40min drops completed, adding 11.25g18-crown ether, maintaining the temperature 0 C, 54.9g of isoamyl nitrite is dripped, about 40min drops completed, the natural return to room temperature.After the system has returned to room temperature, it is heated to 65 degrees reflux overnight (about 12 hours).The next day the TLC test material disappeared, NaHCO3The saturated solution was adjusted to pH = 6, the organic phase was separated, the aqueous phase was extracted once with DCM, the organic phases were combined and dried to dryness, then K2CO3The residue was spin-dried with methanol for about 1 h, filtered and spun dry. The dried residue was then treated with EA and saturated brine. The organic phase was dried to give compound 3 (crude) 29 g, 91.3% yield, which was used directly in Next step.TLC information: Raw Rf = 0.8, Product Rf = 0.5.Developing agent: PE: EA = 1: 1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,76005-99-7, 2-Methoxy-4-methylpyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; Si Fenke Si Pharmaceutical Research And Development (Tianjin) Co., Ltd.; Yao Qingjia; Wu Simin; Xu Yangjun; (7 pag.)CN104230811; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 92276-38-5, 6-Bromo-3H-[1,2,3]triazolo[4,5-b]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, SDS of cas: 92276-38-5, blongs to pyridine-derivatives compound. SDS of cas: 92276-38-5

To a stirred solution of 6-bromo-1H-i,2,3-triazolo[4,5-b]pyridine (250 mg, 1.26 mmol) in DMF (5 mL) at rt was added 60% sodium hydride in mineral oil (55 mg, 1.38 mmol) and the mixture was stirred at rt for 30 mins. (2-(Chloromethoxy)ethyl)trimethylsilane (419 mg, 2.51 mmol) was added and the mixture was stirred for 15 h. The reaction mixture was partitioned between water and EtOAc and the aqueous layer was separated and further extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with 0 – 20% EtOAc in hexanes to afford a 1:1 mixture of 6-bromo- 1 -((2- (trimethylsilyl)ethoxy)methyl)- 1H- [1,2,3 ]triazolo [4,5-b]pyridine and 6-bromo-3 -((2- (trimethylsilyl)ethoxy)methyl)-3H- [1,2,3 ]triazolo[4,5 -b]pyridine (240 mg) as an oil, which was not purified further. LC-MS (ESI) mlz 329 and 331 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,92276-38-5, 6-Bromo-3H-[1,2,3]triazolo[4,5-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; AMBIT BIOSCIENCES CORPORATION; HOLLADAY, Mark, W.; LIU, Gang; ROWBOTTOM, Martin, W.; WO2015/31613; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 13466-35-8 ,Some common heterocyclic compound, 13466-35-8, molecular formula is C5H4ClNO, 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 stirred solution of triphenylphosphine (814 mg, 3.10 mmol) in THF (7 ml) was added DIAD (603 mul, 3.10 mmol) at 0 oC. The mixture was stirred at 0 oC for about 10 min. To this mixture were added 3-chloro-2-hydroxypyridine (321 mg, 2.481 mmol) and tert- butyl 7-hydroxy-4-azaspiro[2.5]octane-4-carboxylate (470 mg, 2.068 mmol). The mixture was slowly warmed up to RT and stirred at RT overnight. The reaction was quenched with the addition of MeOH (~ 2 ml), and the mixture was concentrated and purified by Isco CombiFlash system on silica gel column (ISCO RediSep gold column, 80g) using 0-100%EtOAc/hexane to give the title compound as an oil after concentration. LCMS m/z [M+H]+ 283.13.

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. 13466-35-8, 3-Chloro-2-hydroxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CLAUSEN, Dane; FRADERA, Xavier; GUO, Liangqin; HAN, Yongxin; HE, Shuwen; HUANG, Xianhai; KOZLOWSKI, Joseph; LI, Guoqing; LIM, Jongwon; MARTINOT, Theodore, A.; PASTERNAK, Alexander; SCIAMMETTA, Nunzio; VERRAS, Andreas; XIAO, Li; YU, Wensheng; ZHANG, Rui; (146 pag.)WO2020/41100; (2020); A1;,
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. 98121-41-6, name is 3-Amino-5,6-dichloropyridine, molecular formula is C5H4Cl2N2, 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. Recommanded Product: 98121-41-6

EXAMPLE 2D 5-bromo-2,3-dichloropyridine A 5 L flask with mechanical stirrer, thermocouple, and addition funnel was charged with the product of Example 2C (70 g, 429 mmol) and 48% HBraq (240 mL). The suspension was maintained at 0-5 C. as a solution of NaNO2 (32.0g, 464 mmol) in water (100 mL) was added dropwise over 1 hour. Additional water (200 mL) was added and the mixture was stirred for 10 minutes at 0-5 C. The mixture was treated with CuBr (32.6 g, 227 mmol) in portions over 20 minutes followed by additional water to maintain a fluid reaction mixture. The mixture was allowed to warm to room temperature and diluted with water. The mixture was distilled at ambient pressure, until the distillate ran clear (1.5 L collected). The distillate was extracted with EtOAc (3*500 mL) and the combined extracts were washed with brine (100 mL), dried (MgSO4), and concentrated to provide 5-bromo-2,3-dichloropyridine as a solid. 1H NMR (CDCl3, 300 MHz) delta 7.94 (d, J=3 Hz, 1 H), 8.38 (d, J=3 Hz, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 98121-41-6.

Reference:
Patent; Buckley, Michael J.; Ji, Jianguo; US2004/242641; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 65515-39-1 , The common heterocyclic compound, 65515-39-1, name is 2-Methoxy-4,6-dimethylnicotinonitrile, molecular formula is C9H10N2O, 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.

2-methoxy-4,6-dimethyl-nicotinonitrile (1.0 g, 6.166 mmol) was disolved in 30 mL of anhydrous methylene chloride and then added with 6 mL of trifluoro acetic acid and N-iodosuccinimide (2.2 g, 9.248 mmol) in this order while stirring at 0 C under the nitrogen atmosphere and then stirred again at room temperature for about 4 hours. The mixture was added with 60 mL of a saturated solution of sodium carbonate and 60 mL of a saturated solution of Na2S203 and then extracted twice with 80 mL of methylene chloride. The resulting organic layer was dried with anhydrous sodium sulfate, and filtered. A silica gel column chromatography (5% EtOAc/Hexanes) was performed on the resulting residue and 1.67 g (94%) of 5-iodo- 2-methoxy-4,6-dimethyl-nicotinonitrile was obtained in white solid. 1H NMR (300 MHz, CDC13) 5 2.64 (s, 3H), 2.75 (s, 3H), 4.01 (s, 3H).

The synthetic route of 65515-39-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SK CHEMICALS, CO., LTD.; WO2005/63768; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 41288-96-4, Adding some certain compound to certain chemical reactions, such as: 41288-96-4, name is 2-Chloro-5-hydroxypyridine,molecular formula is C5H4ClNO, 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 41288-96-4.

To a stirred solution of 6-chloropyridin-3-ol (3.0 g, 23.2 mmol) in N,N-dimethylformamide (30 mL) was added iodoethane (4.33 g, 27.8 mmol, 2.22 mL), and potassium carbonate (9.60 g, 69.6 mmol) at 0C. The reaction was warmed and stirred at 40 00 for 2 h. The reaction mixture was quenched by addition of water (30 mL) then the mixture was extracted with ethyl acetate (60 mL x 3). The combined organicphases were washed with saturated aqueous sodium chloride solution (30 mL), dried over anhydrous sodium sulfate, filtered and concentrated to give 2-chloro-5-ethoxypyridine (3.30 g, 20.9 mmol, 90 %) as a yellow solid. 1H NMR (400 MHz, ODd3) O 7.97(d, J2.9 Hz, 1H), 7.17- 7.07(m, 2H), 3.99 (q, J7.0 Hz, 2H), 1 .36 (t, J7.0 Hz, 3H).

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. 41288-96-4, 2-Chloro-5-hydroxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; YUMANITY THERAPEUTICS; LUCAS, Matthew; LE BOURDONNEC, Bertrand; WRONA, Iwona; PANDYA, Bhaumik; TIVITMAHAISOON, Parcharee; OZBOYA, Kerem; VINCENT, Benjamin; TARDIFF, Daniel; PIOTROWSKI, Jeff; SOLIS, Eric; SCANNEVIN, Robert; CHUNG, Chee-Yeun; ARON, Rebecca; RHODES, Kenneth; (489 pag.)WO2018/81167; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 63071-12-5, 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.63071-12-5, name is (6-Methoxypyridin-2-yl)methanol, molecular formula is C7H9NO2, molecular weight is 139.15, as common compound, the synthetic route is as follows.

[0529] Synthesis of 2-(chlorometh -6-methoxypyridine: [0530] To a stirred solution of (6-methoxypyridin-2-yl)methanol (0.7 g 5.03 mmol) in CH2CI2 (20 mL) was added SOCl2 (2 mL) at 0 C under inert atmosphere. The resultant reaction mixture was heated up to 50 C and stirred for 2 h. After completion of starting material (by TLC), the volatiles were evaporated under reduced pressure. The residue was quenched with ice cold water and saturated NaHC03 and extracted with EtOAc. Combined organic layer was dried over sodium sulphate, filtered and concentrated in vacuo. The crude material was purified by silica gel column chromatography to afford 2-(chloromethyl)-6-methoxypyridine (180 mg, 24%) as a liquid. 1H-NMR (DMSO d6, 500 MHz): delta 7.72 (t, 1H), 7.12 (d, 1H), 6.87 (d, 1H), 4.64 (s, 2H), 3.82 (s, 3H); LC-MS: 98.62%; 158.0 (M++l); (column; X- select C-18, (50×3.0 mm, 3.5mu); RT 4.12 min. 5mM NH4OAc in water: ACN; 0.50 ml/min); TLC: 10% EtOAc/Hexane (Rf: 0.6).

Statistics shows that 63071-12-5 is playing an increasingly important role. we look forward to future research findings about (6-Methoxypyridin-2-yl)methanol.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew, J.; BURSAVICH, Matthew, Gregory; WO2013/142269; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem