Category: pyridine-derivatives

Related Products of 886364-86-9, 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. 886364-86-9, name is 5-Bromo-4-methylpicolinonitrile. A new synthetic method of this compound is introduced below.

A mixture of (±)-trans-N-(6-bromo-8-chloroisoquinolin-3-yl)-2-cyanocyclopropane-1-carboxamide (125 mg, 0.571 mmol), bis(pinacolato)diboron (222 mg, 0.856 mmol), potassium acetate (168 mg, 1.711 mmol), and Pd(dppf)Cl2 (42.2 mg, 0.0571 mmol) in 1,4-dioxane (3 mL) was heated in a microwave at 130 C. for 45 minutes to give (±)-(8-chloro-3-((trans-2-cyanocyclopropane-1-carboxamido)isoquinolin-6-yl)boronic acid. LCMS (ESI): [M+H]+=316.0. (0975) 5-Bromo-4-methylpicolinonitrile (168 mg, 0.856 mmol) and sodium carbonate (1 mol/L) in water (2.85 ml, 2.852 mmol) were then added. The reaction mixture was heated in a microwave at 90 C. for 55 minutes. The organic layer was purified with silica gel column chromatography (0.5 to 9% methanol in dichloromethane) to give (±)-(trans-N-(8-chloro-6-(6-cyano-4-methylpyridin-3-yl)isoquinolin-3-yl)-2-cyanocyclopropane-1-carboxamide (187 mg, 86.5% yield). LCMS (ESI) [M+H]+=388.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,886364-86-9, 5-Bromo-4-methylpicolinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Lainchbury, Michael; Gancia, Emanuela; Seward, Eileen; Madin, Andrew; Favor, David; Fong, Kin Chiu; Hu, Yonghan; Good, Andrew; US2018/282282; (2018); 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.105250-16-6, name is (2-Methylpyridin-4-yl)methanol, molecular formula is C7H9NO, molecular weight is 123.15, as common compound, the synthetic route is as follows.category: pyridine-derivatives

Example S4: Preparation of 4- (2-Methyl-pyridin-4-yl)-2H-pyrazol-3-ylamine; a) To a stirred mixture of 4-hydroxymethyl-2-methyl-pyridine [CAS No. 105250-16-6] (3.37 g, 27.4 mmol), potassium cyanide (3.56 g, 54.7 mmol) and 18-crown-6 (0.72 g, 2.74 mmol) in acetonitrile (75 ml) was added dropwise at 15-20C a solution of tributylphosphine (7.16 g, 30.1 mmol) in acetonitrile (25 ml). The reaction mixture was stirred at room temperature for 25 h, poured into water (100 ml) and extracted with ethyl acetate (3 x 100 ml). The combined organic layers were washed with water (3 x 100 ml), brine (100 ml) dried (MgSO4) and evaporated. The crude product was further purified by column chromatography on silica gel (ethyl acetate) to yield 4-cyanomethyl- 2-methyl-pyridine (2.26 g, 62%) as a brown oil

At the same time, in my other blogs, there are other synthetic methods of this type of compound,105250-16-6, (2-Methylpyridin-4-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-ROCHE AG; WO2005/40171; (2005); 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.113118-81-3, name is 5-Bromonicotinaldehyde, molecular formula is C6H4BrNO, molecular weight is 186.0061, as common compound, the synthetic route is as follows.Computed Properties of C6H4BrNO

Intermediate 22(E)-3-Bromo-5-(3-methoxystyryl)pyridine. To a solution of diethyl 3- methoxybenzylphosphonate (5 g, 19.36 mmol) in dimethylformamide (50 mL) at room temperature was added sodium methoxide (2.092 g, 38.7 mmol) and 18-Crown- 6 (2.047 g, 7.74 mmol). After stirring at room temperature for 5 min, the reaction was cooled to 0C and treated with 5-bromonicotinaldehyde (4.32 g, 23.23 mmol) as a solid in one portion. The ice bath was removed and the reaction stirred at room temperature for 2 h. The reaction was poured into water (500 mL) with vigorous stirring. The resulting suspension was extracted with diethyl ether, washed with water (3X), then brine, dried over magnesium sulfate, and concentrated to an oil which crystallized upon standing. The solid was triturated with a minimum of ethanol (ca. 12 mL) and placed in the freezer for 72 h. The resulting solid was broken up with a spatula, collected by filtration, and rinsed with a minimum of cold ethanol to give 3.79 g (68%) as a white crystalline solid. ¾-NMR (CDC13> 500MHz) delta 8.64 (d, J=1.8, IH), 8.57 (d, J=2.1, IH), 8.00 (dd, J=2.1, 1.8, IH), 7.33 (dd, J=7.9, 7.9, IH), 7.10-7.20 (m, 2H), 7.07 (m, IH), 7.01 (d, J=16.5, IH), 6.91 (dd, J=7.6, 2.1, IH), 3.88 (s, 3H). 13C-NMR (CDC13, 126 MHz) delta 160.1, 149.5, 146.7, 137.7, 135.1, 134.8, 132.4, 130.0, 123.7, 121.1, 1 19.6, 1 14.4, 112.2, 55.4. Mass spec: 290.14 (MH)+..

At the same time, in my other blogs, there are other synthetic methods of this type of compound,113118-81-3, 5-Bromonicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DEGNAN, Andrew P.; HUANG, Hong; SNYDER, Lawrence B.; YANG, Fukang; GILLMAN, Kevin W.; PARKER, Michael F.; WO2012/64603; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 17288-35-6 ,Some common heterocyclic compound, 17288-35-6, molecular formula is C8H6N2O2, 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 mixture of 1H-pyrrolo [3 ,2-bj pyridine15 2-carboxylic acid (69 mg, 426 imol, 1 eq), HATU (162 mg, 426 imol, 1 eq), TEA (86 mg, 851 imol, 119 tL, 2 eq) in 2 mL of DMF was stirred at 15C for 0.5 hour, then compound 30(110 mg, 426 imol, 1 eq, HC1 salt) was added at 15C and the mixture was stirred at 15C for 11.5 hours. The mixture was filtered and the filtrate was purified by prep-HPLC (TFA condition) to give 53.5 mg of compound 418 (98 imol, 23% yield, 95.0% purity, TFA salt) as a brown solid. ?H NMR (400MHz, METHANOL-c/4) oe = 8.67 (d, J=5.6 Hz, 1H), 8.62 (d, J=8.3 Hz, 1H), 7.78(dd, J5.7, 8.3 Hz, 1H), 7.69 – 7.27 (m, SH), 7.22 – 6.90 (m, 1H), 3.90 (br s, 1H), 3.66 – 3.48(m, 2H), 3.07 – 2.76 (m, 1H), 2.38 – 2.03 (m, 2H), 2.01 – 1.67 (m, 4H), 1.44 (br t, J=3.7 Hz,2H), 1.42-1.30 (m, 4H), 1.27 (brt,J=7.OHz, 2H), 1.29- 1.24(m, 1H)LCMS (ESI+): m/z 403.3 (M+H)

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. 17288-35-6, 1H-Pyrrolo[3,2-b]pyridine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AQUINNAH PHARMACEUTICALS, INC.; BURNETT, Duane, A.; VACCA, Joseph, P.; (310 pag.)WO2018/119395; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 950670-18-5, name is 3-Bromo-5-fluoropicolinonitrile. A new synthetic method of this compound is introduced below., COA of Formula: C6H2BrFN2

To a suspension of 6-cyclopropyl-2-[(3R)-piperidin-3-yl]-1,2-dihydroisoquinolin-1-one (100.0 mg, 0.33 mmol) in DMF (2 mL) DIPEA (0.2 mL, 0.99 mmol) and 3-bromo-5- fluoropyridine-2-carbonitrile (75 mg, 0.36 mmol) were added. The mixture was stirred at 90C for 3 h, and then it was purified by silica NH flash chromatography with 20 to 100% ethyl acetate in cyclohexane to give 3-bromo-5-[(3R)-3-(6-cyclopropyl-1-oxo-1,2-dihydroisoquinolin- 2-yl)piperidin-1-yl]pyridine-2-carbonitrile (126.0 mg, 85% yield) as a white solid. MS found for C23H21BrN4O as (M+H)+ 449.1, 451.1.

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, 950670-18-5, 3-Bromo-5-fluoropicolinonitrile.

Reference:
Patent; PHARMACYCLICS LLC.; ATALLAH, Gordana, Babic; CHEN, Wei; JIA, Zhaozhong, J.; POZZAN, Alfonso; RAVEGLIA, Lucal, Francesco; ZANALETTI, Riccardo; (815 pag.)WO2016/196776; (2016); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1101120-37-9, 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.1101120-37-9, name is Pyrazolo[1,5-a]pyridin-5-amine, molecular formula is C7H7N3, molecular weight is 133.15, as common compound, the synthetic route is as follows.

Decarboxylation of ester 3l (1.29 g, 2.98 mmol), except with carrying out the aqueous extraction from pH 12, gave pyrazolo[1,5-a]pyridin-5-amine (7l) as a pale brown solid (310 mg, 78%). 1H NMR delta (400 MHz, CDCl3) 8.23 (d, J = 7.4 Hz, 1H), 7.79 (d, J = 2.0 Hz, 1H), 6.58 (d, J = 2.4 Hz, 1H), 6.22 (dd, J = 7.4, 2.4 Hz, 1H), 6.13 (d, J = 2.0 Hz, 1H), 3.81 (s, 2H). LC-MS (APCI+) 134 (MH+, 100%). A solution of NaNO2 (27 mg, 0.39 mmol) in water (1 mL) was added dropwise to a solution of 7l (40 mg, 0.30 mmol) and CuCl (74 mg, 0.75 mmol) in concentrated HCl (1 mL) at 0 C over 2 min. After 30 min, the reaction mixture was heated to 80 C for 15 min, and then cooled to room temperature, basified to pH 10 with 1 M NaOH, filtered through a plug of celite and washed with CH2Cl2. The layers of the filtrate were separated and the aqueous layer extracted with CH2Cl2. The combined extracts were dried (Na2SO4) and the solvent removed in vacuo. Chromatography (eluting with hexanes: EtOAc 3:1) gave 5-chloropyrazolo[1,5-a]pyridine (7o) as a white solid (6 mg, 13%). 1H NMR delta (400 MHz, CDCl3) 8.38 (d, J = 7.4 Hz, 1H), 7.95 (d, J = 2.2 Hz, 1H), 7.53 (d, J = 1.8 Hz, 1H), 6.71 (dd, J = 7.4, 2.2 Hz, 1H), 6.47 (d, J = 1.8 Hz, 1H). LC-MS (APCI+) 153 (MH+ with 35Cl, 100%), 155 (MH+ with 37Cl, 30%). Vilsmeier reaction of 7o (6 mg, 0.039 mmol) gave 4o as a white solid (7 mg, 100%).

Statistics shows that 1101120-37-9 is playing an increasingly important role. we look forward to future research findings about Pyrazolo[1,5-a]pyridin-5-amine.

Reference:
Article; Kendall, Jackie D.; O’Connor, Patrick D.; Marshall, Andrew J.; Frederick, Raphael; Marshall, Elaine S.; Lill, Claire L.; Lee, Woo-Jeong; Kolekar, Sharada; Chao, Mindy; Malik, Alisha; Yu, Shuqiao; Chaussade, Claire; Buchanan, Christina; Rewcastle, Gordon W.; Baguley, Bruce C.; Flanagan, Jack U.; Jamieson, Stephen M.F.; Denny, William A.; Shepherd, Peter R.; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 69 – 85;,
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. 155790-01-5, name is 5-Bromo-N,4-dimethyl-3-nitropyridin-2-amine, the common compound, a new synthetic route is introduced below. Safety of 5-Bromo-N,4-dimethyl-3-nitropyridin-2-amine

5-Bromo-N2,4-dimethylpyridine-2,3-diamineTo a solution of 5-bromo-N,4-dimethyl-3-nitropyridin-2-amine (1000 mg, 4.06 mmol) in EtOH (20 mL) at RT, SnCI2-2 H20 (3668 mg, 16.26 mmol) was added. The reaction mixture was stirred for 1 h. The solvent was evaporated under reduce pressure and saturated NaHC03solution was added to pH=7 then it was extracted with EtOAc (3×40 mL), and the combined organic layers were washed once with brine. The organic layer was concentrated to give 720 mg (82%) of the title compound. LC-MS m/z 216.0, 218.0 (M+H)+, 0.54 (ret. time).

The synthetic route of 155790-01-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; BOEHM, Jeffrey Charles; DAVIES, Thomas Glanmor; WOOLFORD, Alison Jo-anne; GRIFFITHS-JONES, Charlotte Mary; WILLEMS, Hendrika Maria Gerarda; NORTON, David; SAXTY, Gordon; HEIGHTMAN, Thomas Daniel; LI, Tindy; KERNS, Jeffrey K.; DAVIS, Roderick S.; YAN, Hongxing; WO2015/92713; (2015); 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. 15854-87-2, name is 4-Iodopyridine, molecular formula is C5H4IN, 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. name: 4-Iodopyridine

General procedure: A mixture of aryl halide (1.0 mmol), K4[Fe(CN)6](0.22 mmol), 0.05 g [PS-ttet-Pd(II)], and sodium carbonate(1.0 mmol) was stirred in 5 cm3 DMF at 120 C for 1 h under an argon atmosphere. To the aryl nitrile compound generated in situ was added sodium azide (1.5 mmol) and the mixture was stirred at 120 C for appropriate time. After completion of the reaction (as indicated by TLC), the catalyst was centrifuged, washed with EtOH and the residue was diluted with 35 cm3 ethyl acetate and 20 cm3 HCl(4 N) and stirred vigorously. The resultant organic layer was separated and the aqueous layer was extracted with 25 cm3 ethyl acetate. The combined organic layer was washed with 8 cm3 water and concentrated to give a crude product. Column chromatography using silica gel gave thepure product. All products were characterized by 1H NMR and melting point which were in agreement with literature

With the rapid development of chemical substances, we look forward to future research findings about 15854-87-2.

Reference:
Article; Tajbakhsh, Mahmood; Alinezhad, Heshmatollah; Nasrollahzadeh, Mahmoud; Kamali, Taghi A.; Monatshefte fur Chemie; vol. 147; 12; (2016); p. 2135 – 2142;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1082040-63-8, Adding some certain compound to certain chemical reactions, such as: 1082040-63-8, name is 3-Iodo-1H-pyrazolo[3,4-c]pyridine,molecular formula is C6H4IN3, 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 1082040-63-8.

B. Tert-butyl 2-(3-iodo-I H-pyrazolo[3,4-c]pyridi n-I -yI)acetateTo a suspension of 3-iodo-IH-pyrazolo[3,4-c]pyridine (6.24 g, 22.9 mmol) and potassium carbonate (7.29 g, 52.7 mmol) in CH3CN (50 mL) was added dropwise at RT tert-butyl 2- bromoacetate (4.06 mL, 27.5 mmol). The resulting mixture was refluxed for 2 h. The mixture was cooled to RT and filtered, the solid was washed with CH3CN and the filtrate was concentrated and purified by flash column chromatography on silica gel (c-hexane/EtOAc 4:1, then 2:1, then 1:1) to afford the title compound. MS (LC/MS): 360.0 [M+H]+; tR (HPLC conditions d): 2.93 mm.

According to the analysis of related databases, 1082040-63-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; ALTMANN, Eva; HOMMEL, Ulrich; LORTHIOIS, Edwige Liliane Jeanne; MAIBAUM, Juergen Klaus; OSTERMANN, Nils; QUANCARD, Jean; RANDL, Stefan Andreas; VULPETTI, Anna; WO2014/2051; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 59576-26-0, 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 59576-26-0, name is 1-(4-Methylpyridin-2-yl)ethanone. This compound has unique chemical properties. The synthetic route is as follows.

Step 1: In a high pressure vial charged with a solution of 1-(4-methylpyridin-2-yl)ethanone (1.0 equiv.) and EtOH (0.1 equiv) in DCM (2.0M) was added DAST (2.5 equiv.). The reaction was heated to 30 oC and heated for 48 hrs. LCMS analysis indicated the formation of the desired product (MH+?157.9, Rt?0.54 min). The reaction was diluted with DCM and quenched with NaHCO3, slowly at 0oC. The phases were separated and the aqueous layer was washed with DCM (2×). The combined organics were dried over MgSO4, filtered, and concentrated. The crude material was purified via flash chromatography over silica gel eluting with heptanes and 0-100percent ethyl acetate gradient. Isolated 2-(1,1-difluoroethyl)-4-methylpyridine in 27percent yield. LCMS (m/z) (M+H)=157.9, Rt=0.54.

According to the analysis of related databases, 59576-26-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; Barsanti, Paul A.; Burger, Matthew; Lou, Yan; Nishiguchi, Gisele; Polyakov, Valery; Ramurthy, Savithri; Rico, Alice; Setti, Lina; Smith, Aaron; Taft, Benjamin; Tanner, Huw; DiPesa, Alan; Yusuff, Naeem; US2014/275003; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem