Category: pyridine-derivatives

Reference of 578007-66-6 , The common heterocyclic compound, 578007-66-6, name is 5-Bromo-3-iodo-2-methoxypyridine, molecular formula is C6H5BrINO, 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 1: tert-Butyl (1-(4-((5-bromo-2-methoxypyridin-3- yl)ethynyl)phenyl)cyclobutyl)carbamate: To a degassed solution of 5-bromo-3-iodo-2- methoxypyridine (823 mg, 2.62 mmol) in triethylamine (8.0 mL) at 0 C was added Pd(PfBu3)2 (1 10.4 mg, 6 mol%), Cul (5.0 mg, 1 mol%) and terf-butyl (1-(4- ethynylphenyl)cyclobutyl)carbamate (71 1 mg, 2.62 mmol). The brown suspension was stirred for 56 hours at room temperature before the reaction mixture was suspended in dichloromethane and washed with brine, dried over magnesium sulphate, filtered and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (gradient 10 to 25% EtOAc in hexane) to give the title compound as a white solid (1.04 g, 87%). H-NMR (500 MHz, CDCI3) delta 8.14 (d, 1 H), 7.84 (d, 1 H), 7.52 (dd, 2H), 7.41 (d, 2H), 5.13 (bs, 1 H), 4.01 (s, 3H), 2.50-2.56 (m, 4H), 2.09-2.14 (m, 1 H), 1.84-1.90 (m, 1 H), 1.36 (bs, 9H).

The synthetic route of 578007-66-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMAC DISCOVERY LIMITED; BELL, Mark, Peter; O’DOWD, Colin, Roderick; ROUNTREE, James, Samuel, Shane; TREVITT, Graham, Peter; HARRISON, Timothy; MCFARLAND, Mary, Melissa; WO2011/55115; (2011); A1;,
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. 777931-67-6, name is 3-Bromo-2-chloro-6-methoxypyridine, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

Into a 100-mL vial maintained with an inert atmosphere of nitrogen, to a solution of 3-bromo-2-chloro-6-methoxypyridine (2.00 g, 8.900 mmol, 1.00 equiv.) in 1,4-dioxane (20 mL), added Pd(dppf)Cl2.CH2Cl2 (0.36 g, 0.450 mmol, 0.05 equiv.), Zn(CH3)2 (17 mL, 17.000 mmol, 2.00 equiv.). The resulting solution was stirred 16 h at 90 C. The mixture was concentrated under vacuum. The residue product was purified by chromatogram on silica gel with ethyl acetate/petroleum ether (2:98) to yield 2-(6-(1-ethyl-4-fluoro-1H-indazol-6-yl)-2-methoxypyridin-3-yl)-3-methylbutanal as yellow oil. Mass spectrum (ESI, m/z): Calculated for C7H8ClNO, 158.0 [M+H], found 157.8.

The synthetic route of 777931-67-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica NV; Zhang, Xuqing; Macielag, Mark J.; (179 pag.)US2019/47959; (2019); A1;,
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Pyridine | C5H5N – PubChem

Related Products of 89364-04-5 ,Some common heterocyclic compound, 89364-04-5, molecular formula is C5H3BrN2O2, 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 1: 3-(4-bromophenyl)-4-nitropyridine To a stirred solution of 3-bromo-4-nitropyridine (100 g, 492.6 mmol), (4-bromophenyl)boronic acid (98.6 g, 492.6 mmol), and potassium carbonate (203.9 g, 1.47 mol) in toluene (1000 ml)-water (100 ml) was added tetrakis(triphenylphosphine)palladium (14.8 g, 12.8 mmol) at room temperature under nitrogen atmosphere; the mixture was degassed with nitrogen three times. The resulting mixture was stirred at 50 C. overnight. TLC showed the reaction was complete. The solid was removed through filtration and washed with ethyl acetate (100 ml*3). The organic layer was collected and the aqueous layer was extracted with ethyl acetate (100 ml*2). The combined organic layers were washed with brine (400 ml), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a crude residue which was purified by silica gel pad (eluted with 10-33% ethyl acetate in hexane) to afford 3-(4-bromophenyl)-4-nitropyridine (89 g, yield 65%) as 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. 89364-04-5, 3-Bromo-4-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Arvinas, Inc.; Crew, Andrew P.; Berlin, Michael; Flanagan, John J.; Dong, Hanqing; Ishchenko, Alexey; (559 pag.)US2018/125821; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 130473-26-6, 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 130473-26-6, name is 1H-Pyrrolo[2,3-c]pyridine-5-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

C174 (500 mg, 3.42 mmol) is dissolved in 1.5 mL formic acid. The solution is cooled to in an ice bath, 30% aqueous hydrogen peroxide (722 muL, 6.8 mmol) is added drop-wise, and the reaction is stirred 1 h in an ice bath, and allowed to stand overnight at 5 C. The mixture is diluted with water, the solid is collected, washed with water and is dried to give 522 mg of an off-white solid. The formate salt is added to 7 mL water, 3 mL 2N NaOH is added, and the pH is adjusted to 3 with 5% aqueous HCl. The precipitate is collected and is dried to afford 1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid (C176) (67% yield). HRMS (FAB) calculated for C8H6N2O2+H: 163.0508, found 163.0507 (M+H)+.

According to the analysis of related databases, 130473-26-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wishka, Donn G.; Reitz, Steven Charles; Piotrowski, David W.; Groppi JR., Vincent E.; US2003/45540; (2003); A1;,
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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. 122306-01-8, name is (6-Bromopyridin-3-yl)methanol, molecular formula is C6H6BrNO, 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. COA of Formula: C6H6BrNO

To a mechanically-stirred solution of 78.12 g of thionyl chloride in 450 mL of acetonitrile at 15 C. was added a solution of 160.75 g of 3-hydroxymethyl-6-bromopyridine in 446 mL of acetonitrile over 30 minutes. The temperature rose to 22 C. during the addition, and the reaction mixture was stirred for 15 minutes at room temperature. The mixture was cooled in an ice bath, and a solution of 70 g of NaOH in 1.4 L of water was added at such a rate that the temperature did not exceed 15 C. 603 mL of toluene was added to the mixture and stirred rapidly. The layers were separated. The aqueous phase was reextracted with toluene. The combined organic phase was concentrated in vacuo to give 181.61 g of 3-chloromethyl-6-bromopyridine.

With the rapid development of chemical substances, we look forward to future research findings about 122306-01-8.

Reference:
Patent; G. D. Searle & Co.; US5420270; (1995); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 74695-44-6, 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. 74695-44-6, name is 5,7-Dichlorothieno[3,2-b]pyridine, molecular formula is C7H3Cl2NS, 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.

(1) A mixture of 5,7-dichlorotheno[3,2-b]pyridine (0.52 g), triethylamine (0.90 mL), 4-(methylsulfonyl)piperidine mono hydrochloride (0.62 g), and ethylene glycol (1.1 mL) was stirred at 120C for 6 h. Ethylene glycol (4.0 mL) and 1,4-dioxane (4.0 mL) were added, and the mixture was further stirred at room temperature for 16 h. The reaction mixture was diluted with ethyl acetate and washed with saturated brine. The organic layer was dried with anhydrous magnesium sulfate, and then silica gel was added to the organic layer. Silica gel and the desiccant were removed by filtration, the filtrate was concentrated under reduced pressure, and the resulting solids were washed with a mixture solution of ethyl acetate and diisopropyl ether. The resulting solids were purified by silica gel column chromatography (ethyl acetate/hexane = 1:1-1:0) to obtain 5-chloro-7-(4-(methylsulfonyl)piperidin-1-yl)thieno[3,2-b]pyridine (0.11 g).

According to the analysis of related databases, 74695-44-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Taisho Pharmaceutical Co. Ltd.; Nissan Chemical Industries, Ltd.; EP2003131; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1256808-59-9, 5-Fluoro-3-methylpicolinic acid, 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, 1256808-59-9, blongs to pyridine-derivatives compound. Application In Synthesis of 5-Fluoro-3-methylpicolinic acid

5-Fluoro-3-methylpicolinic acid (200 mg, 1.29 mmol) was suspended in dichloromethane (4 mL), the suspension was cooled to 0-5C (ice bath) and oxalyl chloride (435 mg, 300 mu, 3.43 mmol) as well as a drop of a mixture of dimethylformamide and toluene (1 :3, v/v) were added. The mixture was stirred for 1 h at room temperature. Then, it was concentrated in vacuo at 40C, the residue was treated with n-heptane (4 mL) and again concentrated and dried in vacuo (40C, 5 mbar) to afford 5-fluoro-3-methylpicolinoyl chloride as dark brown oil (220 mg). After that, tert-butyl ((4aR,5R,9R)-5-(6-amino-3-fluoropyridin-2-yl)-5,8,8-trimethyl- 9-oxido-2,3 ,4,4a,5 ,8-hexahydro- [ 1 ,4] thiazino [2, 1 -f] [ 1 ,2] thiazin-7-yl)carbamate (Int- 17 A A, 100 mg, 228 muiotaetaomicron) was dissolved in dichloromethane (4 mL), the solution cooled to 0-5C (ice bath) and N,N-diisopropylethylamine (75.5 mg, 100 mu, 584 muiotaetaomicron) was added, followed by a solution of 5-fluoro-3-methylpicolinoyl chloride (vide supra, 50 mg, 288 muiotaetaomicron) in dichloromethane (1 mL). The reaction mixture was stirred at 0-5C for 1.5 h. Then, ethanol (100 mu) was added, the mixture was stirred for 45 min at room temperature, poured onto a saturated aqueous solution of sodium hydrogencarbonate (15 mL) and extracted with dichloromethane (1 x 30 mL, 2 x 20 mL). The combined extracts were dried (sodium sulfate) and concentrated in vacuo. The crude was purified by column chromatography (silica gel, 50 g, eluting with ethyl acetate / n-heptane, gradient 60:40 to 80:20) to afford, after drying in vacuo (50C, 5 mbar), the title compound as a white foam (115 mg, 88% yield). HPLC (method LCMS_gradient) tR = 3.2 min. 1H NMR (CDC13, 400 MHz): delta 1.48 (s, 9 H), 1.79 (s, 3 H), 1.80-2.01 (m, 3 H), 1.85 (s, 3 H), 1.96 (d, J = 1.2 Hz, 3 H), 2.31-2.48 (m, 1 H), 2.83 (s, 3 H), 3.35-3.45 (m, 1 H), 3.56-3.68 (m, 1 H), 4.07-4.14 (m, 1 H), 7.40 (ddd, J = 0.6, 2.7, 8.8 Hz, 1 H), 7.55 (dd, J = 8.9, 10.9 Hz, 1 H), 8.38 (d, J = 2.6 Hz, 1 H), 8.41 (dd, / = 3.0, 8.9 Hz, 1 H), 10.41 (br s, 1 H), 11.23 (br s, 1 H, exch). MS (ES+) m/z 577.3 [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,1256808-59-9, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; CUENI, Philipp; DOLENTE, Cosimo; GUBA, Wolfgang; HAAP, Wolfgang; KUGLSTATTER, Andreas; OBST SANDER, Ulrike; PETERS, Jens-Uwe; ROGERS-EVANS, Mark; VIFIAN, Walter; WOLTERING, Thomas; (231 pag.)WO2016/55496; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 176526-00-4, 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 176526-00-4, name is 2-(Pyridin-4-yl)benzaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

6.5. Synthesis of (S)-2-Amino-3-(4-{6-[2,2,2-trifluoro-1-(2-pyridin-4-yl-phenyl)-ethoxy]-pyrimidin-4-yl}-phenyl)-propionic acid Tetrabutylammonium fluoride (0.027 ml; 1.0 M solution in tetrahydrofuran) was added to a solution of 2-pyridin-4-yl-benzaldehyde (500 mg, 2.73 mmol) and trifluoromethyltrimethylsilane (TMSCF3) (485 mul, 3.28 mmol) in 5 ml of THF at 0 C. The formed mixture was warmed up to room temperature and stirred at room temperature for 4 hours. The reaction mixture was then treated with 5 ml of 1N HCl and stirred at room temperature overnight. The solvent was evaporated to dryness, 9 ml of 1M sodium carbonate aqueous solution was added, the aqueous phase was extracted with chloroform (3*10 ml), and the combined organic layer was washed with water, dried over MgSO4. The organic solvent was evaporated to give 300 mg of 2,2,2-trifluoro-1-(2-pyridin-4-yl-phenyl)ethanol, yield: 43%.

According to the analysis of related databases, 176526-00-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jin, Haihong; Shi, Zhi-Cai; Tunoori, Ashok; Wang, Ying; Zhang, Chengmin; Devasagayaraj, Arokiasamy; US2008/153852; (2008); A1;,
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. 145255-19-2, name is 5-Aminopyridine-2-carboxamide, the common compound, a new synthetic route is introduced below. Application In Synthesis of 5-Aminopyridine-2-carboxamide

[1160] 50 mg (0.121 mmol) of 2-[4-(5-chloro-2-cyano- phenyl)-5-methoxy-2-oxopyridin-1 (2H)-yl] -3 -(5-methyl-i, 2,4-oxadiazol-3-yl)propanoic acid (racemate) and 25 mg(0.181 mmol, 1.5 eq.) of 5-aminopyridine-2-carboxamide were initially charged in 1.0 ml of pyridine, 114 jtl (0.4 82 mmol, 50% in ethyl acetate, 4.0 eq.) of T3P were added and the mixture was stirred at 500 C. for 1.5 h. The reaction mixture was cooled, 4 ml of water and 4 ml of saturated aqueous sodium hydrogencarbonate solution were added and the mixture was stirred for 10 mm. The suspension was filtered with suction and washed with water and three times with 2 ml each time of acetonitrile, and then the filtrate was lyophilized Yield: 51 mg (80% of theory).11161] LC/MS [Method 1]: R=0.81 mm; MS (ESIpos):mlz=534 (M+H),11162] ?H-NMR (400 MHz, DMSO-d6): oe [ppm]=10.90(s, 1H), 8.85 (d, 1H), 8.21 (dd, 1H), 8.05-8.00 (m 2H), 7.98(d, 1H), 7.75-7.67 (m, 2H), 7.56-7.50 (m, 2H), 6.51 (s, 1H),5.98 (dd, 1H), 3.80-3.62 (m, 5H), 2.53 (s, 3H)

The synthetic route of 145255-19-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ROeHRIG, Susanne; JIMENEZ-NUNEZ, Eloisa; SCHLEMMER, Karl-Heinz; TERSTEEGEN, Adrian; TELLER, Henrik; HILLISCH, Alexander; HEITMEIER, Stefan; SCHMIDT, Martina Victoria; ACKERSTAFF, Jens; STAMPFUss, Jan; (87 pag.)US2017/291892; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 64951-08-2 ,Some common heterocyclic compound, 64951-08-2, 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 l-(3-((5-aminopyridin-3-yl)amino)-5-methyl-5H-chromeno[4,3- c]pyridin-8-yl)pyrrolidin-2-one (60 mg, 0.14 mmol, HC1 salt), imidazo[l,2-a]pyridine-2- carboxylic acid (34 mg, 0.21 mmol) and EDCI.HC1 (41 mg, 0.21 mmol) in pyridine (2 mL) was stirred at 50 C for 2 h. The reaction mixture turned into white suspension from yellow solution. LCMS (Rt = 0.750 min; MS Calcd: 531.2; MS Found: 532.1 [M+H]+). The reaction mixture was diluted with water (25 mL), and then extracted with EtOAc/THF (25 mL x3, 1/1). The combined organic layer was washed with saturated aqueous NaHCCh (25 mL), brine (25 mL), dried over anhydrous Na2S04 and concentrated. The residue was triturated with MeCN (10 mL), then further purified by prep-HPLC (0.225% FA as an additive). Most of the MeCN was removed under reduced pressure and the remaining part was lyophilized to give N-(5-((5- methyl-8-(2-oxopyrrolidin-l-yl)-5H-chromeno[4,3-c]pyridin-3-yl)amino)pyridin-3- yl)imidazo[l,2-a]pyridine-2-carboxamide (29.8 mg, yield: 40%) as ayellow solid. (1680) NMR (400 MHz, DMSO-rie) d 1.56 (3H, d, J= 6.5 Hz), 2.01-2.11 (2H, m), 2.52-2.54 (2H, m), 3.85 (2H, t, J= 7.9 Hz), 5.29 (1H, q, J= 6.4 Hz), 6.79 (1H, s), 7.05 (1H, td, J= 6.8, 1.1 Hz), 7.33 (1H, dd, J= 8.7, 2.1 Hz), 7.39-7.44 (2H, m), 7.69 (1H, dd, J= 9.2, 0.9 Hz), 7.90 (1H, d, J= 8.8 Hz), 8.58 (1H, s), 8.59 (1H, t, J= 2.3 Hz), 8.65 (1H, td, J= 6.8, 1.1 Hz), 8.69 (1H, d, J= 2.3 Hz), 8.70 (1H, s), 8.78 (1H, t, J= 2.3 Hz), 9.52 (1H, brs), 10.51 (1H, brs).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,64951-08-2, its application will become more common.

Reference:
Patent; PETRA PHARMA CORPORATION; KESICKI, Edward A.; LINDSTROeM, Johan; PERSSON, Lars Boukharta; VIKLUND, Jenny; FORSBLOM, Rickard; GINMAN, Tobias; HICKEY, Eugene R.; DAHLGREN, Markus K.; GERASYUTO, Aleksey I.; (391 pag.)WO2019/126730; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem