Day: September 14, 2021

Reference of 72990-37-5 ,Some common heterocyclic compound, 72990-37-5, molecular formula is C6H4ClNO, 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.

Reference Production Example 4 To a mixture of 1.53 g of 3-chloroisonicotinaldehyde and 5 ml of ethanol was gradually added 0.40 g of sodium borohydride under ice-cooling, and the mixture was stirred under ice-cooling for 1 hour, and subsequently at room temperature for 1 hour. Saturated brine was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The organic layers were combined and dried over magnesium sulfate. The resulting mixture was concentrated under reduced pressure to obtain 1.40 g of (3-chloropyridin-4-yl)methanol. 1H-NMR (CDCl3) delta: 8.54-8.49 (m, 2H), 7.55-7.51 (m, 1H), 4.83 (d, J=4.4 Hz, 2H), 2.34-2.29 (br m, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,72990-37-5, its application will become more common.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; Iwakoshi, Mitsuhiko; Takyo, Hayato; US2013/90353; (2013); 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 1211540-79-2, name is 2,3-Dihydro-1H-pyrrolo[3,2-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C7H8N2

To a solution of 2,3-dihydro-1 H-pyrrolo[3,2-b]pyridine (9.05 g, 75.3 mmol) and dichloropyrimidine (12.3 g, 75.3 mmol) in te/t-butanol (90 mL) and toluene (90 mL) was added cesium carbonate (37.6g). The mixture was degassed with a stream of nitrogen gas. Bis(triphenylphosphine)palladium(ll) dichloride (1.59 g) was added and the mixture was again degassed with nitrogen for several minutes. The resulting mixture was heated at reflux (115 degrees Celsius) for 18 hours. The mixture was cooled to room temperature, diluted with ethyl acetate and the mixture was filtered through diatomaceous earth. The filtrate was concentrated in vacuo to an oil. This oil was dissolved in 2-methyl tetrahydrofuran (400 mL) and 300 mL of 1 N aqueous hydrochloric acid was added. The aqueous layer was separated and extracted twice with 2-methyl tetrahydrofuran. The combined organic extracts were washed with water. The combined aqueous layers were cooled in an ice bath and triethylamine was added slowly until the pH was adjusted to 8 to 9. A precipitate formed and these solids were collected by filtration. The aqueous filtrate was extracted twice with 2-methyl tetrahydrofuran. These combined organic extracts were washed with brine, dried over sodium sulfate, filtered and the filtrate was concentrated in vacuo. The residue was combined with the previously collected solids, dissolved in 2-methyl tetrahydrofuran and concentrated in vacuo. The reside was purified by flash chromatography using 330 g of silica gel, eluting with a gradient mixture of heptane and ethyl acetate (50 to 100% over 30 min and then 100% ethyl acetate for 30 min) to give 1-(6-chloro-5-methylpyrimidin-4-yl)-2,3- dihydro-1 H-pyrrolo[3,2-b]pyridine as an off-white solid (25.5 g). 1H NMR (400 MHz, deuterochloroform) delta 2.27 (s, 3 H) 3.29 (t, J=8.39 Hz, 2 H) 4.18 (t, J=8.39 Hz, 2 H) 7.03 (dd, J=8.10, 4.98 Hz, 1 H) 7.20 (dd, J=8.10, 1.27 Hz, 1 H) 8.07 (dd, J=5.08, 1.37 Hz, 1 H) 8.47 (s, 1 H)

With the rapid development of chemical substances, we look forward to future research findings about 1211540-79-2.

Reference:
Patent; PFIZER INC.; DAROUT, Etzer; DENINNO, Michael, Paul; FUTATSUGI, Kentaro; GUIMARAES, Cristiano, Ruch, Werneck; LEFKER, Bruce, Allen; MASCITTI, Vincent; MCCLURE, Kim, Francis; MUNCHHOF, Michael, John; ROBINSON, Ralph, Pelton, Jr.; WO2010/128414; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1659-31-0, 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. 1659-31-0, name is Dipyridin-2-yl carbonate. A new synthetic method of this compound is introduced below.

Under nitrogen atmosphere, to a stirred mixture of (4-cyclohexylphenyl)-methanol (0.3 g, 1.58 mmol) in dry CH2C12 (2 mL), DMAP (0.019 g, 0.16 mmol) and di-2-pyridyl- carbonate (0.41 1 g, 1.90 mmol) were added. The reaction mixture was left to react at rt for 15 h, then diluted with CH2C12 and washed first with a saturated NH4C1 solution (3.0 mL) and subsequently with a saturated NaHC03 solution (3X3 mL). The organic fraction was dried over Na2S04, filtered and concentrated to dryness to afford a colorless oil (0.464 g, 95%), as a mixture (ratio 1.8: 1) of (4-cyclohexylphenyl)-methyl-2-pyridyl carbonate and (4- cyclohexylphenyl)-methy 1-2 -oxopyridine-1 -carboxylate. The mixture of isomers was not separated and used in the next step without any further purification. MS (ESI) m/z 350 [M- K]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1659-31-0, Dipyridin-2-yl carbonate, and friends who are interested can also refer to it.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; IIT – ISTITUTO ITALIANO DI TECNOLOGIA; UNIVERSITY DEGLI STUDI DI URBINO; UNIVERSITA DEGLI STUDI DI PARMA; PIOMELLI, Daniele; BANDIERA, Tiziano; MOR, Marco; TARZIA, Giorgio; BERTOZZI, Fabio; PONZANO, Stefano; WO2013/78430; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 70201-42-2, 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.70201-42-2, name is 3,5-Dibromoisonicotinaldehyde, molecular formula is C6H3Br2NO, molecular weight is 264.9, as common compound, the synthetic route is as follows.

To a solution of cesium carbonate (9.20 g, 28.2 mmol) and 4-phenylphenol (2.40 g, 14.1 mmol) in anhydrous THF (100 mL) under an inert atmosphere was added a solution of 3,5-dibromopyridine-4-carboxaldehyde (7.48 g, 28.2 mmol) in THF (25 mL). The reaction mixture was heated at reflux for 4 hours then was allowed to cool to room temperature. The reaction mixture was filtered and the solvent was removed in vacuo. The residue was diluted with EtOAc, washed with aqueous sodium bicarbonate, washed with brine, and dried over sodium sulfate then filtered and the solvent removed in vacuo. Purification by silica gel (eluting with 20% EtOAc: heptane) followed by recrystallization from heptane afforded 3- (bipfienyl-4-yloxy )-5-bronio-pyridine-4-carbaldehyde (4.39 g, 12.4 mmol, 87%); (at)H-NMR (DMSO-d6, 400 MHz) : 8 7.23 (m, 2H), 7.38 (m, 1H), 7.47 (m, 2H), 7.66 (m, 2H), 7.73 (m, 2H), 8.43 (s, 1H). RP-HPLC (Table 1, Method i) R(at) = 3.72 min.

Statistics shows that 70201-42-2 is playing an increasingly important role. we look forward to future research findings about 3,5-Dibromoisonicotinaldehyde.

Reference:
Patent; ABBOTT LABORATORIES; WO2005/110410; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 100-48-1, Isonicotinonitrile, 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, 100-48-1, blongs to pyridine-derivatives compound. COA of Formula: C6H4N2

General procedure: 0.01mol nitrile dissolved in 10 ml ethanol. After that, 0.011 mol hydroxylamine hydrochloride, 10 ml water and 1.23g sodium acetate was added as followed, stirred in room temperature for 0.5 h then refluxed in 50-60 for 8 h. The ethanol was mostly evaporated in vacuum and then the aqueous residue was extracted with CH2Cl2 three times. The combined organic layer was dried over MgSO4 and evaporated to dryness to afford the desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,100-48-1, its application will become more common.

Reference:
Article; Su, Dongshan; Duan, Haifeng; Wei, Zhonglin; Cao, Jungang; Liang, Dapeng; Lin, Yingjie; Tetrahedron Letters; vol. 54; 50; (2013); p. 6959 – 6963;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 105752-11-2, 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.105752-11-2, name is 3-Amino-4-iodopyridine, molecular formula is C5H5IN2, molecular weight is 220.0111, as common compound, the synthetic route is as follows.

2,6-dichloro-[3,4′-bipyridin]-3′-amine (i64): To a stirred solution of 4-iodopyridin-3-amine (2 g, 9.0 mmol) in 1 ,4-dioxane (84 ml_), (2,6- dichloropyridin-3-yl) boronic acid (2.4 g, 12.5 mmol) and K3P04 (5.6 g, 26.0 mmol) solution in water (28 mL) were added and the reaction was degassed with argon for 20 min. PdCI2(PPh3)2 (0.7 g, 0.99 mmol) was added and the reaction was heated in a sealed tube at 100C for 16 h. The progress of the reaction was monitored by TLC. After completion, the reaction was diluted with water and filtered. The aqueous layer was extracted with ethyl acetate. The organic layer was separated, dried over anhydrous sodium sulphate and concentrated under reduced pressure. The crude product was purified by silica gel (100:200 mesh) column chromatography using 2% methanol in dichloromethane as eluent to afford 2,6-dichloro-[3,4′-bipyridin]-3′-amine (64) (1 .08 g, Yield 51 %). 1 H NMR (400 MHz, DMSO-d6) delta 5.26 (s, 2H), 6.93 (d, J = 4.9 Hz, 1 H), 7.51 -7.68 (m, 1 H), 7.79- 7.89 (m, 2H), 8.08 (s, 1 H), MS (ESI) m/e (M+1 )+: 240.00

Statistics shows that 105752-11-2 is playing an increasingly important role. we look forward to future research findings about 3-Amino-4-iodopyridine.

Reference:
Patent; UCB BIOPHARMA SPRL; MERCIER, Joel; PROVINS, Laurent; VERMEIREN, Celine; SABNIS, Yogesh Anil; (106 pag.)WO2016/124508; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 955369-63-8, 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.955369-63-8, name is Ethyl 2-(6-bromopyridin-2-yl)acetate, molecular formula is C9H10BrNO2, molecular weight is 244.09, as common compound, the synthetic route is as follows.

To a mixture of ethyl 2-(6-bromo-2-pyridyl)acetate (2.00 g, 8.19 mmol) in THF (10 mL), water (10 mL) and MeOH (20 mL) was added LiOH.H2O (1.03 g, 24.5 mmol). Then the reaction mixture was stirred at 20 C for 2 hours. On completion, the reaction mixture was concentrated in vacuo. The residue was acidified by 1.0 N HCl to pH = 3.0, washed with water (150 mL) and extracted with ethyl acetate (3 X 150 mL). The organic layer was dried with Na2SO4, filtered and concentrated in vacuo to give the title compound (1.70 g, 96% yield) as a yellowish solid.1H NMR (400MHz, DMSO-d6) delta = 12.63 (br. s., 1H), 7.86 – 7.71 (m, 1H), 7.59 (d, J = 8.0 Hz, 1H), 7.46 (d, J = 7.6 Hz, 1H), 3.81 (s, 2H).

Statistics shows that 955369-63-8 is playing an increasingly important role. we look forward to future research findings about Ethyl 2-(6-bromopyridin-2-yl)acetate.

Reference:
Patent; RAZE THERAPEUTICS, INC.; MAINOLFI, Nello; (215 pag.)WO2018/106636; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 55304-73-9, 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.55304-73-9, name is 2,6-Dichloro-3-formylpyridine, molecular formula is C6H3Cl2NO, molecular weight is 176, as common compound, the synthetic route is as follows.

Example 27 c. 2-((2,6-dichloropyridin-3-yl)methylamino)-l-(l,3-dimethyl-lH- pyrazol-5-yl)ethanol2,6-Dichloronicotinaldehyde (0.964 g, 5.48 mmol), 2-amino-l -(1,3 -dimethyl- lH-pyrazol- 5-yl)ethanol (0.810 g, 5.22 mmol) and acetic acid (0.149 ml, 2.61 mmol) in methanol (10 mL) was stirred at room temperature for 20 minutes. Methanol (15 mL) was added and cooled to 00C. Sodium cyanoborohydride (0.394 g, 6.26 mmol) was added and the reaction mixture was stirred at 00C for 10 minutes. The solvent was evaporated and the residue was partitioned between dichloromethane and sat. NaHCO3 (aq). The water layer was extracted twice with dichloromethane and the combined organic layer was dried (MgSO4) and concentrated. The crude product was purified by silica column chromatography using a gradient of methanol (0 to 5%) in dichloromethane giving 1.5O g of the title compound (91 % Yield). 1H NMR (500 MHz, DMSO-J6) delta ppm 7.99 (dd, 1 H), 7.52 – 7.63 (m, 1 H), 5.90 (s, 1 H), 5.37 (dt, 1 H), 4.63 – 4.76 (m, 1 H), 3.76 – 3.86 (m, 2 H), 3.65 – 3.75 (m, 3 H), 3.17 (dt, 1 H), 2.69 – 2.87 (m, 2 H), 2.01 – 2.16 (m, 3 H). MS m/z 315, 317, 319 [M+H] +.

Statistics shows that 55304-73-9 is playing an increasingly important role. we look forward to future research findings about 2,6-Dichloro-3-formylpyridine.

Reference:
Patent; ASTRAZENECA AB; LO-ALFREDSSON, Yvonne; PAULSEN, Kim; RAKOS, Laszlo; ROTTICCI, Didier; WALDMAN, Magnus; WO2010/132015; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 2402-78-0 , The common heterocyclic compound, 2402-78-0, name is 2,6-Dichloropyridine, molecular formula is C5H3Cl2N, 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.

A solution of n-BuLi (21.1 ml_, 33.8 mmol, 1.6 M) in THF is cooled to -78C before a solution of 2,6-dichloropyhdine (5.0 g, 33.8 mmol) in THF (36 ml_) is added dropwise over a period of 20 min. The reaction mixture is stirred at -78C for 30 min, and then iodomethane (4.79 g, 33.8 mmol) is added. The mixture is stirred for 30 min before it is quenched with sat. aq. NH4CI solution at -78C. The mixture is extracted with diethyl ether, the org. extract is dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 19:1 to give 2,6-dichloro-4-methyl-pyridine (2.34 g) as a colourless oil containing the regio isomer 2,6-dichloro-3-methyl-pyhdine; LC-MS: tR = 0.89 min, [M+1]+ = 161.97.

The synthetic route of 2402-78-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2009/24905; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 19798-80-2, 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. 19798-80-2, name is 4-Chloropyridin-2-amine, molecular formula is C5H5ClN2, 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.

To a solution of 4-chloropyridin-2-amine (3 g, 23.2 mmol) in DMSO (60 mL) was added sodium methoxide (12.6 g, 232 mmol) and the mixture was then stirred at 150 C for 3 hours then poured into ice-water. The product was extracted with EtOAc (2×100 mL), and the combined organic layers were washed with water (50 mL) and brine (50 mL), dried (Na2S04) and concentrated. The residue was purified by silica gel chromatography using a solvent system of 50% petroleum ether/EtOAc to give 4-methoxypyridin-2-amine (460 mg, 16%) as a yellow solid MS ESI calc’d for C6H8N20 [M + H]+ 125, found 125.

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 19798-80-2, 4-Chloropyridin-2-amine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ANDRESEN, Brian, M.; ANTHONY, Neville, J.; MILLER, Thomas, A.; WO2014/74422; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem