Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 1072-97-5, 5-Bromopyridin-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, 1072-97-5, blongs to pyridine-derivatives compound. category: pyridine-derivatives

Example 4 Preparation of compound 8: 1. An ethanol solution of compound 5 (12400 g in 51 L of ethanol) was added to an appropriately sized stainless steel reactor at room temperature under nitrogen atmosphere. 2. Compound 6 (9500 g) was added as a solid in one portion at room temperature. 3. The reaction mixture was heated to reflux (?78C) and stirred for 1-2 days. 4. The reaction was monitored by HPLC. 5. Upon completion, the reaction mixture was allowed to cool to room temperature. 6. NaOH solution (9884 g solid pellets dissolved in 38 L of water) was added as a stream over a 30 min period at an internal temperature below 35 C. 7. The reaction mixture was heated to reflux (?78C) for 3 to 4 hours. 8. The reaction was monitored by HPLC. 9. Upon completion, the reaction mixture was cooled to an appropriate temperature to start solvent removal. 10. All ethanol (approximately 5 volumes of ethanol) was removed under vacuum at 40 to 45 C. 11. The reaction mixture was cooled to room temperature. 12. Water (57 L; 6 vol) was added at room temperature. 13. The aqueous solution was washed with ethyl acetate (2 x 38 L) to remove all organic impurities. 14. The lower aqueous layer was cooled to 0-5 C and acidified with cone. HCl (?15 L) until reaching pH 1-2. 15. The reaction mixture was stirred for 1 to 2 hours at 0 to 5 C. 16. The mixturewas filtered and the cake was washed with water (2 x 38 L) and acetone (2 x 19L) followed by drying for 1-2 hours. 17. The solid collectedwas transferred back into an appropriately sized reactor. 18. Heptane (95 L; 10 vol) was addedto the reactor; the suspension was stirred for 4 to 5 hours at roomtemperature. 19. The solidwas collected by filtration and washed with heptane (2 x 19 L). 20. The solid (15 kg) was suspended in methanol (75 L; 5 vol) at room temperature for 2 hours. 21. The suspension was filtered and the solid collected was washed with methanol (2x 5L). 22. The solid was dried under vacuum at 50C to constant weight to give compound 8 as an off-white to white solid (10169 g, 83.3 % yield; HPLC purity 99.2%;1HNMR (DMSO-d6, 300 MHz) delta 9.4 (s, 1H), 8.3 (s, 1H), 7.85-7.67 (m, 2H)).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1072-97-5, its application will become more common.

Reference:
Patent; IP Gesellschaft fuer Management mbH; Trinius, Frank; EP2792360; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 14529-54-5, 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. 14529-54-5, name is 3,5-Dibromo-1-methylpyridin-2(1H)-one. A new synthetic method of this compound is introduced below.

Example 130a 5-Bromo-1-methyl-3-(1-methyl-1H-imidazol-4-ylamino)pyridin-2(1H)-one 130a A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 1,4-dioxane (50 mL), 1-methyl-1H-imidazol-4-amine (1.1 g, 11.3 mmol), 3,5-dibromo-1-methylpyridin-2(1H)-one (3.0 g, 11.3 mmol), Pd2(dba)3 (1.0 g, 1.13 mmol), XantPhos (1.3 g, 2.26 mmol), and cesium carbonate (7.3 g, 22.6 mmol). After three cycles of vacuum/argon flush, the mixture was heated at 92 C. for 4.5 hrs. It was then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica-gel column chromatography eluting with dichloromethane/methanol (100:1 to 50:1) to afford 130a (2.4 g, 76%) as a yellow solid. MS-ESI: [M+H]+ 283.1

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14529-54-5, 3,5-Dibromo-1-methylpyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; GENENTECH, INC.; Crawford, James John; Ortwine, Daniel Fred; Wei, BinQing; Young, Wendy B.; US2013/116246; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 571189-49-6, Adding some certain compound to certain chemical reactions, such as: 571189-49-6, name is 5-(4-Methylpiperazin-1-yl)pyridin-2-amine,molecular formula is C10H16N4, 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 571189-49-6.

General procedure: Pd2(dba)3 (86.4mg, 0.09mmol) and Xant-phos (109.2mg, 0.19mmol) were added under N2 to a solution of 154 1E (290.0mg, 0.94mmol), INT-7 (228.6mg, 1.04mmol), and 152 potassium phosphate (400.5mg, 1.88mmol) in 111 1,4-dioxane (10mL). Then the mixture was reacted in the microwave at 150C for 1h. The mixture was cooled to RT, filtered, diluted with water (10mL), and extracted with DCM (10mL×3). The combined organic layers were washed with brine (30mL), dried over anhydrous Na2SO4, concentrated under a vacuum, and purified by preparative thin-layer chromatography to obtain 157 compound 1 (140.3mg; yield, 30%) as a yellow solid.

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. 571189-49-6, 5-(4-Methylpiperazin-1-yl)pyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Yin, Lei; Li, Heng; Liu, Wenjian; Yao, Zhenglin; Cheng, Zhenzhen; Zhang, Huabei; Zou, Hui; European Journal of Medicinal Chemistry; vol. 144; (2018); p. 1 – 28;,
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.63071-10-3, name is (4-Chloropyridin-2-yl)methanol, molecular formula is C6H6ClNO, molecular weight is 143.57, as common compound, the synthetic route is as follows.Computed Properties of C6H6ClNO

Method XXVI(4-chloropyridin-2-yl)methyl methanesulfonateTo a solution of (4-chloropyridin-2-yl)methanol (3 g, 20.90 mmol) in dichloromethane (60 ml) was added triethylamine (2.90 mL, 20.90 mmol) and methanesulfonyl chloride (1.617 mL, 20.90 mmol) at 0 C. The reactionmixture was stirred at 20 C for 30 min. The reaction was quenched with addition of water. The reaction mixture was extracted with dichloromethane and the organic layer dried (magnesiumsulphate) and evaporated.Purification with flash silica chromatography with elution gradient ethylacetate in petroleumeter 20 to 40%. Fractions containing product was evaporated to give the title compound (4.13 g, 89%). m/z (APCI) (M+H)+ 222.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,63071-10-3, (4-Chloropyridin-2-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BENGTSSON, Boel, Ase; BLACKABY, Wesley; CUMMING, John; FAULL, Alan, Wellington; LARSSON, Joakim; NASH, Ian, Alun; OLDHAM, Keith; PAPE, Andrew; WO2011/114148; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 4214-73-7, 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. 4214-73-7, name is 2-Amino-5-cyanopyridine, molecular formula is C6H5N3, 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.

6-aminonicotinonitrile (10 g, 80 mmol) in acetonitrile (300 mL) was treated with a 50% aqueous solution of 2-chloroacetaldehyde (26.4 mL, 210 mmol). The mixture was stirred and heated to reflux. After 6 hours, the mixture was cooled to room temperature. The mixture was concentrated to low bulk (approx. 100 mL), treated with saturated aqueous sodium hydrogencarbonate solution to neutral pH, and then extracted with dichloromethane (2 x 300 mL). The organic layer was dried (MgSO4) and evaporated and the residue was stirred with diethyl ether (200 mL), filtered and dried in vacuum to give the title compound (22.54 g, 94%) as a pale brown solid.LRMS (m/z): 144 (M+1)+.1H-NMR delta (CDCI3): 7.29 (dd, 1 H), 7.71 (d, 1 H), 7.73 (d, 1 H), 7.80 (d, 1 H), 8.61-8.62 (m, 1 H)

According to the analysis of related databases, 4214-73-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Almirall, S.A.; Eastwood, Paul Robert; Gonzalez Rodriguez, Jacob; Bach Tana, Jordi; Pages Santacana, Lluis Miquel; Taltavull Moll, Joan; Caturla Javaloyes, Juan Francisco; EP2338888; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1990-90-5, 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. 1990-90-5, name is 3-Methylpyridin-4-amine, molecular formula is C6H8N2, 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.

The crude 2-(5-chloro-2-fluorophenyl)-4-iodo-5,6,7,8-tetrahydroquinazoline (130 mg, 0.35 mmol, 1 eq) was dissolved in dioxane (5 ml) and to this was added Pd(OAc)2 (4 mg, 0.02 mmol, 0.05 eq) followed by BINAP (16 mg, 0.03 mmol, 0.075 eq), 4-amino-3-picoline (49 mg, 0.45 mmol, 1.3 eq) and Cs2CO3 (170 mg, 0.52 mmol,1.5 eq). The reaction mixture was heated to 80C for 15 h. The reaction mixture was cooled to r.t. and filtered through Celite and the crude material was purified by flash column chromatography (l:l/ethyl acetate:hexane) to afford [2-(5-chloro-2-fluoro- EPO phenyl)-5,6,7,8-tetrahydroquinazolin-4-yl]-(3-methylpyridin-4-yl)-amine, compound of formula (38) (110 mg, 86%)

According to the analysis of related databases, 1990-90-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD.; WO2006/35061; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 55304-72-8 , The common heterocyclic compound, 55304-72-8, name is 2,3,6-Trichloro-5-nitropyridine, molecular formula is C5HCl3N2O2, 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.

5,6-Chloro-iV-(5-cvclopropyl-l//-pyrazol-3-yl)-3-nitropyridine-2-amine To a solution of 2,3,6-trichloro-5-nitropyridine (1.62 g, 7.10 mmol) and DIEA (1.24 ml, 7.1 mmol) in THF (25 ml) was added dropwise a solution of 5-cyclopropyl-lH”-pyrazol-3- amine (0.70 g, 5.68 mmol) in THF (5 ml) at 0 0C. After addition, the reaction mixture was stirred at 25 0C for 24 hours. The solvent was removed under reduced pressure and the resulted residue was purified by column chromatography (hexane : EtOAc = 1.5 : 1) to give the title compound as a yellow solid (0.83 g, 47%). NMR (400 MHz) 12.39 (s, IH), 10.12 (s, IH), 8.77 (d, J= 1.2 Hz, IH), 6.35 (s, IH), 1.95 (m, IH), 0.96 (m, 2H), 0.71 (m, 2H). MS: Calcd.: 313; Found: [M+H]+ 314.

The synthetic route of 55304-72-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/87530; (2006); A1;,
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. 97483-77-7, name is 5-Bromopicolinonitrile. This compound has unique chemical properties. The synthetic route is as follows. Safety of 5-Bromopicolinonitrile

The organically modified hectorite-loaded ionic liquid material prepared by the first embodiment of the present invention (abbreviated as MHIL) is used as a catalyst for catalytic condensation to prepare an intermediate for the treatment of diabetes drugs 5-[(3R)-3-methylperazine Pyrazin-1-yl]pyridine-2-carbonitrile (CN 101400653A),The reaction is shown in Scheme3:5-bromo-2-cyanopyridine (10 mmol, 1.81 g) under nitrogen atmosphere,Catalyst MHIL (0.36g, 20wt%),(R)-(-)-2-methylpiperazine (1.3 g, 13 mmol) was placed in 20 ml of dimethyl sulfoxide at 100-110 C. After 8 h, the reaction liquid was HPLC-detected for substrate 5-bromine- 2-cyanopyridine was not detected. The catalyst was filtered to remove MHIL. The filtrate was added with 20 ml of a 3 M% aqueous solution of methylamine, and then extracted twice with 20 ml of dichloromethane. The methyl chloride layer is concentrated under reduced pressure5-[(3R)-3-methylpiperazin-1-yl]pyridine-2-carbonitrile 1.88 g, yield 93%, HPLC purity 99.86%, LC-MS: m/z = 203.1 [M +H].The organic modified hectorite-loaded ionic liquid material prepared by the invention (abbreviated as MHIL) is used as a catalyst for preparing an intermediate for the treatment of diabetes drugs 5-[(3R)-3-methylpiperazin-1-yl] Pyridine-2-carbonitrile does not require the addition of precious metal palladium as compared to CN 101400653A, and the yield is significantly improved.Although the embodiments of the present invention have been described in detail, it is understood that various changes, modifications and changes may be made in the embodiments of the present invention without departing from the spirit and scope of the invention.

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, 97483-77-7, 5-Bromopicolinonitrile.

Reference:
Patent; Zheng Chuanhua; Lu Xueling; Zhang Lei; (10 pag.)CN109369517; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 78607-36-0, 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.78607-36-0, name is 2-Chloro-3-iodopyridine, molecular formula is C5H3ClIN, molecular weight is 239.44, as common compound, the synthetic route is as follows.

Example 1 :N-(2-(2,6-Dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-yl)cyclopropanecarboxamideStep 1 :2-Chloro-4-iodonicotinaldehydeA mixture of 2-chloro-3-iodopyridine (5.0 g, 21 mmol) in dry THF (30 mL) was slowly added to a cold (-78 C) solution of lithium diisopropylamide (15 mL, 30 mmol) in dry THF (50 mL). The resulting mixture was stirred for 3 h at this temperature. Ethyl formate (4.0 g, 54 mmol) was then added. Stirring was continued for 1.5 h at the same temperature. Water (10 mL) was added to quench the reaction, and then the resulting mixture was warmed to room temperature. 2M HC1 (50 mL) was added and then the THF was removed under reduced pressure. The aqueous residue was extracted with ethyl acetate (2 x 50 mL). The combined organic extracts were washed with brine, dried over Na2S04 and concentrated under reduced pressure. The residue was purified on silica gel (diethyl ether: petroleum ether = 1 : 4) to give the desired product 2-chloro- 4-iodonicotinaldehyde as a yellow solid (3.0 g, 54% yield). NMR (500 MHz, CDC13): delta 10.22 (s, 1H), 8.09 (d, J = 5.0 Hz, 1H), 7.95 (d, J = 5.0 Hz, 1H).

The chemical industry reduces the impact on the environment during synthesis 78607-36-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BLENCH, Toby; GOODACRE, Simon; LAI, Yingjie; LIANG, Yun; MACLEOD, Calum; MAGNUSON, Steven; TSUI, Vickie; WILLIAMS, Karen; ZHANG, Birong; WO2012/66061; (2012); A1;,
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. 78686-79-0, name is Methyl 5-bromo-2-chloronicotinate. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: Methyl 5-bromo-2-chloronicotinate

Compound WX069-1 (7.00 g, 27.95 nmol) wasdissolved in dimethyl sulfoxide solution (50.00 mE) at roomtemperature, followed by the addition of cesium fluoride(8.00 g, 52.67 mmol) at room temperature. The reactionmixture was heated to 550 C. and stirred for 14 hours. Afterthe reaction, the mixture was cooled to room temperature,quenched with saturated brine (10 mE), diluted with water(50 mE) and extracted with ethyl acetate (20 mLx3). Thecolunm c1omatography (eluent: petroleum ether/ethylorganic phases were separated, washed with water (50mEx2) and dried over anhydrous sodium sulfate, followedby filtration. The filtrate was concentrated under reducedpressure. The obtained residue was isolated by silica gelacetate1 00/1 – 100/15, volume ratio) to obtain the targetproduct WX069-2. ?H NMR (400 MHz, CDC13) oe: 8.64-8.31 (m, 2H), 3.98 (s, 3H).

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, 78686-79-0, Methyl 5-bromo-2-chloronicotinate.

Reference:
Patent; SHIJIAZHUANG SAGACITY NEW DRUG DEVELOPMENT CO., LTD.; LUO, Yunfu; YANG, Chundao; LEI, Maoyi; LIU, LING; HU, Guoping; LI, Jian; CHEN, Shuhui; US2019/177318; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem