Pyridine-derivatives

Electric Literature of 130115-85-4, 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. 130115-85-4, name is 5-Bromo-6-chloropyridin-3-ol, molecular formula is C5H3BrClNO, 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 diethyl azodicarboxylate (1.89 mL, 12.0 mmol) in THF (30 mL) was added triphenylphosphine (3.15 g, 12.0 mmol) at 0C, and the reaction mixture was stirred for 0.5 hour. 1-BOC-(S)-pyrrolidinemethanol (2.41 g, 12.0 mmol) and 5-bromo-6-chloropyridine-3-ol (2.09 g, 10.0 mmol) were then added. The reaction mixture was allowed to warm to room temperature overnight. The solvent was removed, and the residue was chromatographed on a silica gel column, eluting with EtOAc/hexane (1:5 and 1:2) to afford an oil (3.80 g, 97%). MS (CI/NH3) m/z 391,393 (M+H)+. 1H NMR (DMSO-d6, 300 MHz) delta 1.65-2.05 (m, 4H), 3.20-3.35 (m, 2H), 3.95-4.15 (m, 3H), 7.98 (d, J = 2.9 Hz, 1H), 8.21 (d, J = 2.9 Hz, 1H).

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 130115-85-4, 5-Bromo-6-chloropyridin-3-ol.

Reference:
Patent; Abbott Laboratories; EP1047690; (2004); B1;,
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.139022-25-6, name is Imidazo[1,2-a]pyridine-6-carboxylic acid, molecular formula is C8H6N2O2, molecular weight is 162.15, as common compound, the synthetic route is as follows.Product Details of 139022-25-6

(5-(([2 ‘-Bipyridin]-3-yloxy)methyl)-4,5-dihydroisoxazol-3-yl)methanamine hydrochloride (±) (product of step-2, 0.320 g, 0.997 mmol) was reacted with imidazo[l,2- a]pyridine-6-carboxylic acid (0.193 g,1.197 mmol) in presence of BOP reagent (0.485 g, 1.096 mmol) and DIPEA (0.525 mL, 2.991 mmol ) in DMF (10 mL) at room temperature for 16 h. The reaction mixture was diluted with water (10 mL) extracted with ethyl acetate (50 mL) and washed with water (4 x 50 mL). The organic phase was dried over sodium sulphate and concentrated under reduced pressure to get a residue. The residue was purified by combiflash column chromatography (dichloromethane/methanol/triethylamine = 91/8/1) to afford the title compound (0.150 g, 35%) as a solid. LCMS: nt/z 428.7 [M+H] +; HPLC: 97.93 % ; NMR (400 MHz, DMSO-de): delta 9.16 – 9.12 (d, / = 1.8 Hz, 1H), 9.11 (s, 1H), 9.05 – 8.99 (t, / = 5.5, 5.5 Hz, 1H), 8.61 – 8.54 (dt, / = 3.3, 1.5, 1.5 Hz, 1H), 8.37 – 8.31 (d, / = 4.5 Hz, 1H), 8.30 – 8.25 (m, 1H), 8.11 (s, 1H), 7.68 – 7.60 (m, 4H), 7.51 – 7.45 (dd, / = 7.9, 4.8 Hz, 1H), 7.45 – 7.39 (dd, / = 8.4, 4.6 Hz, 1H), 5.01 – 4.91 (dq, / = 10.4, 5.6, 5.6, 5.4 Hz, 1H), 4.28 – 4.12 (m, 4H), 3.27 – 3.15 (dd, / = 17.6, 11.2 Hz, 1H), 3.00 – 2.86 (dd, / = 17.7, 7.1 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,139022-25-6, Imidazo[1,2-a]pyridine-6-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; CHIKKANNA, Dinesh; KHAIRNAR, Vinayak; (74 pag.)WO2016/12958; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 128372-89-4, 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. 128372-89-4, name is tert-Butyl 2-oxo-5,6-dihydropyridine-1(2H)-carboxylate, molecular formula is C10H15NO3, 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.

General procedure: A dried Schlenk flask was charged with arylboronic acid (3, 0.4 mmol), [Rh(L1)(OH)]2 (L1=(S,S)-Ph-thpe, 3.8 mg, 0.005 mmol), KHF2 (3.2 mg, 0.04 mmol), and 1 mL of anhydrous toluene under argon. The resulting mixture was stirred at room temperature for 30 min. 1-N-Boc-2-oxo-5,6-dihydropyridine (2c, 39.4 mg, 0.2 mmol) in toluene (1 mL) was added. Seven minutes later, 0.1 mL of isopropanol was added. After being stirred at room temperature for 2 h, the reaction was quenched with saturated aq NH4Cl, extracted with ethyl acetate (20 mL×3), and the combined organic phases were washed with brine, dried with anhydrous Na2SO4, filtered, and concentrated. The residue was purified by silica gel (300-400 mesh) column chromatography to afford 4.

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 128372-89-4, tert-Butyl 2-oxo-5,6-dihydropyridine-1(2H)-carboxylate.

Reference:
Article; He, Zhi-Tao; Wei, Ya-Bing; Yu, Hong-Jie; Sun, Cai-Yun; Feng, Chen-Guo; Tian, Ping; Lin, Guo-Qiang; Tetrahedron; vol. 68; 45; (2012); p. 9186 – 9191;,
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. 113293-71-3, name is (6-Aminopyridin-3-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H8N2O

To a stirring suspension of (6-aminopyridin-3-yl)methanol (1 .24 mg, 10.0 mmol) and ethyl 2-chloro-3-hydroxyacrylate, potassium salt (29) (3.76 g, 20.0mmol) in EtOH (10 mL) at room temperature was added cone sulfuric acid (1 0.0 mmol) dropwise. The reaction mixture was stirred at room temperature for 15 minutes and pyridine (0.92 g, 12.0 mmol) was added. The resulting mixture was heated at 85 C overnight. The reaction was cooled to room temperature and the solvent was concentrated. The residue was taken in water and the solution was adjusted to pH 8 with saturated sodium bicarbonate. The crude product was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The crude product ethyl 6- (hydroxymethyl)imidazo[1 ,2-a]pyridine-3-carboxylate (59) was purified by silica chromatography. 1 H NMR (400MHz, c/6-DMSO) delta 9.16 (d, J = 6.8 Hz, 1 H), 8.26 (s, 1 H), 7.67 (s, 1 H), 7.19 (dd, J = 1 .6, 6.8 Hz, 1 H), 5.57 (t, J = 6.4 Hz, 1 H), 4.63 (d, J = 6.0, 2H), 4.36 (q, J = 7.2 Hz, 2H), 1 .35 (t, J = 6.8 Hz, 3H). MS m/z 221 .1 (M+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, 113293-71-3, (6-Aminopyridin-3-yl)methanol.

Reference:
Patent; IRM LLC; LOREN, Jon; LI, Xiaolin; LIU, Xiaodong; MOLTENI, Valentina; NABAKKA, Juliet; NGUYEN, Bao; PETRASSI, Hank Michael James; YEH, Vince; RUCKER, Paul Vincent; WO2013/33203; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 133427-08-4, 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.133427-08-4, name is Imidazo[1,2-a]pyridine-8-carboxylic acid, molecular formula is C8H6N2O2, molecular weight is 162.15, as common compound, the synthetic route is as follows.

Step E: Preparation of (4-(2,4-Difluorophenethyl)piperazin-l-yl)(imidazo[l,2- alpha]pyridin-8-yl)methanone (Compound 3).To a solution of imidazo[l,2-alpha]pyridine-8-carboxylic acid (36.6 mg, 226 mumol), l-(2,4- difluorophenethyl)piperazine hydrochloride (45.0 mg, 150 mumol) and triethylamine (210 mul, 1504 mumol) in DMF (0.75 mL) was added 1-propylphosphonic acid anhydride solution (50% in ethyl acetate, 183 muL, 0.301 mmol). The mixture was stirred for 2 h, quenched with water and purified by preparative HPLC/MS. The resultant lyophilate was dissolved in DCM, treated with MP-carbonate resin (-200 mg). The mixture was stirred for 30 min and filtered to remove the resin. The solvent was removed under reduced pressure to afford the title compound as a white solid (33.0 mg).

Statistics shows that 133427-08-4 is playing an increasingly important role. we look forward to future research findings about Imidazo[1,2-a]pyridine-8-carboxylic acid.

Reference:
Patent; ARENA PHARMACEUTICALS INC.; WO2009/23253; (2009); A2;,
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. 147149-98-2, name is 4-Amino-2-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 147149-98-2

POCl3 (98.85 mg, 0.65 mmol) was added to a mixture of 1-(2-methylimidazo[1,2-a]pyridin-5-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid (100 mg, 0.32 mmol), 2-(trifluoromethyl)pyridin-4-amine (52.26 mg, 0.32 mmol), pyridine (127.49 mg, 1.61 mmol) in CH2Cl2 (3 mL) at rt. The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was quenched with 20 mL sat. K2CO3 aq, and extracted with CH2Cl2 (20 mL*3). The organic layer was separated and concentrated under reduced pressure. It was purified by preparative high-performance liquid chromatography (35% to 65% (v/v) CH3CN and H2O with 0.05% ammonia hydroxide). The pure fractions were collected and the organic solvent was concentrated under reduced pressure. The aqueous layer was lyophilized to dryness to give the desired product as a white solid. (80 mg, purity: 99.5%, yield: 54.3%). LCMS (ESI) m/z M+1: 454.9. 1H NMR (400 MHz, DMSO-d6) delta ppm 2.32 (s, 3H), 7.08 (s, 1H), 7.32 (d, J=7.06 Hz, 1H), 7.41 (dd, J=9.04, 7.28 Hz, 1H), 7.75 (d, J=9.04 Hz, 1H), 7.94 (dd, J=5.73, 1.76 Hz, 1H), 8.21 (d, J=1.76 Hz, 1H), 8.65 (s, 1H), 8.69 (d, J=5.29 Hz, 1H), 11.29 (s, 1H).

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, 147149-98-2, 4-Amino-2-(trifluoromethyl)pyridine.

Reference:
Patent; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1206979-33-0, 6-Chloro-1H-pyrazolo[4,3-c]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, Product Details of 1206979-33-0, blongs to pyridine-derivatives compound. Product Details of 1206979-33-0

To a mixture of tert-butyl 4-(6-bromopyridin-2-yl)-6-methoxy-6-methyl-1,4-diazepane-1-carboxylate (530 mg, 1.33 mmol) and 6-chloro-1H-pyrazolo[4,3-c]pyridine (203 mg, 1.33mmol) in 1,4-dioxane (30 mL) was added Cul (101 mg, 0.53 mmol), N1,N2-dimethylethane-1,2-diamine (94 mg, 1.06 mmol), and K2CO3 (734 mg, 5.32 mmol). The mixture was heated at 100C, which was monitored by LCMS. After completion of the reaction, it was concentrated under reduced pressure. The crude material was purified by silica gel chromatography using petroleumether:EtOAc (3:1~1:1) as eluting solvents to afford tert-butyl 4-(6-(6-chloro-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-6-methoxy-6-methyl-1,4-diazepane-1-carboxylate as yellow solid. (446 mg, 71%). MS (ESI) m/z: 473 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1206979-33-0, 6-Chloro-1H-pyrazolo[4,3-c]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; DO, Steven; HU, Huiyong; KOLESNIKOV, Aleksandr; TSUI, Vickie, H.; WANG, Xiaojing; WO2014/1377; (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 1122-71-0, name is 6-Methyl-2-pyridinemethanol. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

A mixture of 6-methyl-2-pyridylmethanol (145 mg, 1.17 mmol) and sodium hydroxide (63 mg, 1.57 mmol) in benzene (15 mL) was heated to reflux for 3 hours with stirring under nitrogen atmosphere and then cooled to 25 C. followed by the addition of compound 133 (0.30 g, 0.785 mmol) at same temperature. The mixture was heated to reflux for 12 hours, concentrated under vacuum and diluted with water (20 mL). The mixture was then extracted with EtOAc (2*20 mL). The combined organic layers were washed with water (2*10 mL), dried over anhydrous sodium sulphate and concentrated under vacuum. The residue thus obtained was purified by column chromatography (70-80% EtOAc-Hexane) to afford the title compound E30 as a hygroscopic solid (257 mg, 70%). HPLC: Inertsil ODS 3V (250*4.6 mm) 5 microns [solvent A=0.01 M KH2PO4 (pH 7.0); solvent B=CH3CN], Gradient elution program: T/% B=0/60, 10/60, 25/80, 40/80, 45/60, 50/60; 268 nm, Rt 23.93 min, 99.14% purity; MS (CI): m/z 469 (M+, 100).

With the rapid development of chemical substances, we look forward to future research findings about 1122-71-0.

Reference:
Patent; Timmer, Richard T.; Alexander, Christopher W.; Pillarisetti, Sivaram; Saxena, Uday; Yeleswarapu, Koteswar Rao; Pal, Manojit; Reddy, Jangalgar Tirupathy; Krishma Reddy, Velagala Venkata Rama Murali; Sesila Sridevi, Bhatlapenumarthy; Kumar, Potlapally Rajender; Reddy, Gaddam Om; US2004/209882; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 67139-79-1 ,Some common heterocyclic compound, 67139-79-1, molecular formula is C7H4Cl2N2, 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.

Step 2; Synthesis of 4-(2 4-Dichloro-benzeloxy)-5-(2, 4-dichloro-benzyloxamethyl .- 2- (4, 6-dichloro-pyrrolo [3, 2-c] pyridin-1-yl-3-methyl-tetrahydro-furan-3-ol; To a solution of the base prepared in step 1 above (1.01 g, 5.4 mmol) in 150 mL anhydrous acetonitrile under argon at room temperature was added sodium hydride (60%, 260 mg, 6.5 mmol). The solution was allowed to stir for 4 h. To a solution of the ss-D-1-O-methyl-2, 3, 5,-tri (2,4-dichlorobenzyl)-ribofuranose (sugar Y) (1.11 g, 2.2 mmol) in 75 mL anhydrous dichloromethane under argon at 0C was added 0.86 mL HBr (30%) dropwise. The resulting solution was allowed to stir at 0 for 1 h and then at room temperature for 3 h. The solution was then evaporated in vacuo and coevaporated with toluene. The residue was dissolved in 50 mL anhydrous acetonitrile and added to the solution of the sodium salt of base prepared in Step 1 above. The combined mixture was stirred at room temperature for 24 h, and then evaporated to dryness. The residue was dissolved in EtOAc, and washed with water. The water was extracted 3x with EtOAc. The combined organic extracts were washed with brine and dried with Na2S04. The solvent was removed in vacuo. Column chromatography with silica gel using 30% ethyl acetate in hexane was used for final purification. The title nucleoside was isolated as a dark brown oil (724.3 mg, 51%).

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. 67139-79-1, 4,6-Dichloro-1H-pyrrolo[3,2-c]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GENELABS TECHNOLOGIES, INC.; WO2003/93290; (2003); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 7205-46-1, Adding some certain compound to certain chemical reactions, such as: 7205-46-1, name is 6-Chloro-1-methyl-1H-imidazo[4,5-c]pyridine,molecular formula is C7H6ClN3, 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 7205-46-1.

6-Chloro-l-methyl-lH-imidazo[4,5-c]pyridine (2.52 g, 0.015 mol) was stirred with 4,5- bis(diphenylphosphino)-9,9-dimethylxanthene (0.86 g, 0.0015 mol), sodium-tert-butoxide (2.16 g, 0.0225 mol) and 4-(4-methoxybenzyloxy)-2-methylaniline (3.68 g, 0.015 mol) in dry dioxane (50 mL) under N2 (g) for 30 minutes. Tris(dibenzylideneacetone)dipalladium(0) (0.68 g, 0.00075 mol) was added and the mixture was stirred at 100C for 4.5 h. The mixture was concentrated in vacuo and the residue was treated with water (50 mL) and extracted into EtOAc (2 x 300 mL). The combined extracts were washed with brine, dried (MgSO i), filtered and concentrated in vacuo to give a solid which was recrystalised from isopropanol to give the desired compound. [00306] NMR delta (ppm)(DMSO-d6): 8.43 (1 Eta, d, ArH), 7.98 (1 H, s, NH), 7.75 (1 H, s, ArH), 7.39 (2 H, d, ArH), 7.27 (1 H, d, ArH), 7.00-6.90 (3 H, m, ArH), 6.82 (1 H, dd, ArH), 6.38 (1 H, d, ArH), 5.00 (2 H, s, CH), 3.77 (3 H, s, CH3), 3.64 (3 H, s, CH3), 2.17 (3 H, s, CH3).

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. 7205-46-1, 6-Chloro-1-methyl-1H-imidazo[4,5-c]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GALAPAGOS NV; MENET, Christel; SCHMITT, Benoit; GENEY, Raphael; DOYLE, Kevin; PEACH, Joanne; PALMER, Nicholas; JONES, Graham; HARDY, David; DUFFY, James; WO2013/117649; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem