Pyridine-derivatives

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

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

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

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

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

Application of 54221-96-4 ,Some common heterocyclic compound, 54221-96-4, molecular formula is C7H7NO2, 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.

6-Methoxy-2-pyridinecarboxaldehyde (1.0 mL, 8.31 mmol) and 2-naphthylamine (1.19 g,8.33 mmol) were dissolved in 25 mL of anhydrous methanol and the resulting mixture washeated at reflux temperature for 6 h. The solvent was removed under reduced pressure togive brown solids. Yield: 1.58 g (72percent). Anal. Calcd (percent) for C17H14N2O (M = 262.31 g mol?1): C,77.84; H, 5.38; N, 10.68. Found: C, 77.88; H, 5.43; N, 10.71. FT-IR (KBr, cm?1): 3439(w), 3051(w),2976(w), 2840(w), 1632(m), 1586(s), 1569(m), 1508(w), 1467(s), 1438(m), 1413(w), 1350(w),1334(m), 1321(m), 1267(s), 1229(w), 1208(w), 1167(w), 1151(m), 1120(w), 1078(w), 1032(m),985(w), 961(w), 911(w), 887(w), 860(s), 824(m), 808(s), 750(s), 734(w), 666(w), 626(w), 603(w),523(w), 504(w), 478(w), 430(w). 1H NMR (400 MHz, CDCl3): delta 8.63 (s, 1H, CH = N), 7.52?7.87(m, 7H, Naphthalene-H), 6.84?7.02 (m, 3H, Py-H3,4,5), 4.03 (s, 3H, ?OCH3) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,54221-96-4, its application will become more common.

Reference:
Article; Dong, Yu-Wei; Wang, Ping; Fan, Rui-Qing; Chen, Wei; Wang, A-Ni; Yang, Yu-Lin; Journal of Coordination Chemistry; vol. 70; 11; (2017); p. 1953 – 1972;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 677728-92-6, 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 677728-92-6, name is 2-Fluoropyridine-5-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 24: (trans-4-{ri-(5-formylpyridin-2-yl)piperidin-4-yl1oxy|cvclohexyl)acetic acidA mixture of [trans-4-(piperidin-4-yloxy)cyclohexyl] acetic acid (0.8 g, 3.32 mmol), 3- fluoro-5-formylpyridine (0.415 g, 3.32 mmol) and sodium bicarbonate (1.67 g, 19.89 mmol) in NMP (6 ml) was heated at 110C in an oil bath over night under N2. The reaction mixture was cooled to room temperature then concentrated under vacuum. The residual was applied onto a silica gel column and eluted with acetone/dichloromethane 0-100%. This resulted in 0.28 g (24.4%) of: (trans-4-{[l-(5-formylpyridin-2-yl)piperidin-4-yl]oxy}cyclohexyl)acetic acid as a white solid. LC-MS (ES, m/z): Ci9H26N204: 346; Found: 347 [M+H]+.

According to the analysis of related databases, 677728-92-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INTERVET INTERNATIONAL B.V.; DE VITA, Robert, J.; HONG, QingMei; LAI, Zhong; DYKSTRA, Kevin, D.; YU, Yang; LIU, Jian; SPERBECK, Donald; JIAN, Tianying; GUIADEEN, Deodial; XU-QIANG YANG, Ginger; WU, Zhicai; HE, Shuwen; TING, Pauline, C.; ASLANIAN, Robert; KUETHE, Jeffrey, T.; BALKOVEC, James, M.; KUANG, Rongze; ZHOU, Gang; WU, Heping; WO2012/164071; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1174229-72-1, Ethyl 2-(6-aminopyridin-3-yl)acetate, 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, 1174229-72-1, blongs to pyridine-derivatives compound. Recommanded Product: 1174229-72-1

A 20-mL vial was charged with 4-chloro-2-(3-chlorophenyl)-6- cyclopropylpyrimidine (0.380 g, 1.43 mmol), ethyl 2-(6-aminopyridin-3-yl)acetate (0.410 g, 2.27 mmol), palladium acetate (0.016 g, 0.071 mmol), rac-BINAP (0.069 g, 0.11 mmol) and cesium carbonate (1.17 g, 3.58 mmol) in dioxane (10 mL) under argon. The reaction mixture was heated to 110 C under microwave irradiation for 1.25 h. The reaction mixture was cooled, and diluted with ethyl acetate and filtered through celite. The filtrate was washed with saturated sodium chloride (2 x 10 mL), dried over sodium sulfate, filtered, and the filtrate concentrated under reduced pressure. The residue was purified by chromatography on silica using hexanes/ethyl acetate (10:0 to 0: 10) as eluent to afford the title compound (0.504 g, 86%) as an off-white solid. MW = 408.88. M.p. 133-135 C. ]H NMR (DMSO- , 500 MHz) delta 10.13 (s, 1H), 8.31-8.29 (m, 1H), 8.27 (dt, / = 7.0, 1.5 Hz, 1H), 8.22 (d, / = 2.0 Hz, 1H), 7.75-7.68 (m, 2H), 7.62 (br s, 1H), 7.59-7.52 (m, 2H), 4.10 (q, / = 7.5 Hz, 2H), 3.68 (s, 2H), 2.07 (septet, / = 4.5 Hz, 1H), 1.21 (t, / = 7.0 Hz, 3H), 1.14-1.10 (m, 2H), 1.06-1.00 (m, 2H); APCI MS m/z 409 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1174229-72-1, its application will become more common.

Reference:
Patent; TETRA DISCOVERY PARTNERS, LLC.; GURNEY, Mark, E.; HAGEN, Timothy, J.; MO, Xuesheng; VELLEKOOP, A.; ROMERO, Donna, L.; CAMPBELL, Robert, F.; WALKER, Joel, R.; ZHU, Lei; WO2014/66659; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6188-23-4, 6-Bromoimidazo[1,2-a]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, Recommanded Product: 6188-23-4, blongs to pyridine-derivatives compound. Recommanded Product: 6188-23-4

A mixture of the compound of example 1 (1.0 g, 5.08 mmol) and t-butyl 4-(5-(4, 4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1-carboxylate (1.97 g, 5.08 mmol) were treated with [1 ,1 ‘-bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.124 g, 0.152 mmol) and sodium carbonate (2.15 g, 20.30 mmol) in dry dimethylformamide (100 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 1.05 g (54.68 %); 1H NMR (DMSO-d6, 300 MHz): delta 1.39 (s, 9H, 3CH3), 3.44 (s, 4H, 2CH2), 3.55 (s, 4H, 2CH2), 6.95 (d, 1H, J=8.7 Hz, Ar), 7.50-7.62 (m, 3H, Ar), 7.87 (d, 1H, J=2.4 Hz, Ar), 7.90 (s, 1H, Ar), 8.46 (d, 1H, J=2.4 Hz, Ar), 8.83 (s, 1H, Ar); MS (ES+): m/e 380 (M+1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6188-23-4, 6-Bromoimidazo[1,2-a]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; PIRAMAL ENTERPRISES LIMITED; SHARMA, Rajiv; GHOSH, Usha; MORE, Tulsidas; KULKARNI, Mahesh; BAJAJ, Komal; BURUDKAR, Sandeep; RIZVI, Zejah; WO2014/80241; (2014); 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 13472-81-6, name is 3,5-Dibromo-2-hydroxypyridine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C5H3Br2NO

3,5-Dibromo-2-hydroxypyridine (9.36 g, 37 mmol; purchased from Tokyo Chemical Industry Co., Ltd.), 1,4-butane sultone (6.58 g, 48.3 mmol), and NaOH (1.97 g, 49.3 mmol) were added to 160 mL of ethanol, and the mixture was stirred for 24 h at 60 C. The white precipitate was separated by filtration, and recrystallization from THF containing a small amount of water gave Monomer-1 (7.17 g, 47%). 1H NMR (300 MHz, D2O) delta: 7.93 (d, J = 2.4 Hz, 1H), 7.77 (d, J = 2.4 Hz, 1H), 3.90 (t, J = 6.9 Hz, 2H), 2.78 (t, J = 7.5 Hz, 2H), 1.71 (m, 2H), 1.60 (m, 2H). IR (KBr) 1656, 1593, 1188, 1052 cm-1. Anal. Calcd for C9H10Br2NNaO4S: C, 26.30%; H, 2.45%; Br, 38.88%; N, 3.41%; S, 7.80%. Found: C, 25.80%; H, 2.52%; Br, 39.04%; N, 3.34%; S, 7.71%.

With the rapid development of chemical substances, we look forward to future research findings about 13472-81-6.

Reference:
Article; Yamamoto, Takakazu; Takei, Tohru; Kumagai, Naoto; Harada, Yosuke; Ohki, Takumi; Kudoh, Yasuo; Kojima, Takahiro; Koizumi, Take-Aki; Shiramizu, Kohei; Abe, Masahiro; Oota, Masashi; Polymer; vol. 53; 26; (2012); p. 5995 – 5999;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem