Pyridine-derivatives

Synthetic Route of 850429-51-5, 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. 850429-51-5, name is Ethyl 6-amino-5-bromonicotinate, molecular formula is C8H9BrN2O2, 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.

A) To a solution of ethyl 6-amino-5-bromonicotinate (2.31 g, 10 mmol) in tetrahydrofuran (20 mL) at RT was added LAH (10 mL, IM in tetrahydrofuran) dropwise. After stirring for Ih, the mixture was quenched with water (0.2 mL) and the resultant precipitate was filtered and washed with ethyl acetate. The filtrate was concentrated in vacuo to afford (6-amino-5-bromopyridin-3-yl)methanol (2.0 g, 99%) as a solid. LC/MS; (M+H)+ = 203, 205 (1 : 1 ratio). 1H NMR (CD3OD, 300 MHz) delta 7.79 (s, IH), 7.67 (s, IH), 4.35 (br S, 2H).

According to the analysis of related databases, 850429-51-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/60907; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 147740-04-3, Adding some certain compound to certain chemical reactions, such as: 147740-04-3, name is Ethyl 1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate,molecular formula is C10H12N2O2, 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 147740-04-3.

d) 2,3-Dihydro-1H-pyrrolo[3,4-c]pyridine dihydrochloride 10.4 g (51 mmol) of ethyl 2,3-dihydro-1H-pyrrolo-[3,4-c]pyridine-2-carboxylate are refluxed for 15 hours together with 100 ml of concentrated hydrochloric acid. The batch is evaporated, and the crystalline residue is stirred with acetone. The product is filtered off with suction and dried in the air. Yield: 9.8 g (100percent of theory)

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. 147740-04-3, Ethyl 1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bayer Aktiengesellschaft; US5312823; (1994); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 709652-82-4 , The common heterocyclic compound, 709652-82-4, name is 2-Amino-5-bromonicotinonitrile, molecular formula is C6H4BrN3, 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.

Example 126 Step 1: (6-amino-5-cyanopyridin-3-yl)boronic acid and 2-amino-5-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)nicotinonitrile To a stirred solution of 2-amino-5-bromonicotinonitrile (100 mg, 0.51 mmol) and 1,2- dimethoxyethane (4 mL) in a microwave vial equipped with a stirbar was added bis(pinacolato diborane) (175 mg, 0.66 mmol), potassium acetate (149 mg, 1.52 mmol) and 1,1′- bis(diphenylphosphino)ferrocene-palladium(II)dichloride (21 mg, 0.025 mmol). The mixture was purged with nitrogen gas for 5 min and the reaction mixture was stirred at 90 C for 3 h. The reaction mixture was filtered through a celite bed and washed with dichloromethane (10 mL). The filtrate was concentrated to dryness in vacuo affording a crude mixture of (6-amino-5-cyanopyridin-3-yl)boronic acid and 2-amino-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)nicotinonitrile used for the next step without any further purification. Step 2: 2-amino-5-(4-cyclopropyl-6,6-dimethyl-8,9-dihydro-6H-[l,4]oxazino[4,3-e]purin-2- yl)nicotinonitrile 2-chloro-4-cyclopropyl-6,6-dimethyl-8,9-dihydro-6H-[l,4]oxazino[4,3-e]purine (50 mg, 0.18 mmol) and a crude mixture of (6-amino-5-cyanopyridin-3-yl)boronic acid and 2-amino-5-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)nicotinonitrile (120 mg) was dissolved in acetonitrile (2.5 mL) and degassed water (0.5 mL) in a microwave vial equipped with a stirbar. To the solution was added bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (12.7 mg, 0.018 mmol), potassium acetate (25 mg, 0.25 mmol) and sodium carbonate (27 mg, 0.25 mmol) and the mixture was microwaved at 140 C for 40 min. The reaction mixture was filtered through a celite bed and washed with dichloromethane (10 mL). The filtrate was concentrated to dryness in vacuo. The resulting residue was purified by RP-HPLC affording 2-amino-5-(4-cyclopropyl-6,6-dimethyl-8,9-dihydro-6H- [l,4]oxazino[4,3-e]purin-2-yl)nicotinonitrile (4.1 mg, 6%, two steps): LCMS RT = 5.07 min, m/z = 362.2 [M + H]+.

The synthetic route of 709652-82-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; HUESTIS, Malcolm; KELLAR, Terry; PATEL, Snahel; SHORE, Daniel; SIU, Michael; (260 pag.)WO2016/142310; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1019021-85-2, 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.1019021-85-2, name is 6-Fluoroimidazo[1,2-a]pyridine-3-carboxylic acid, molecular formula is C8H5FN2O2, molecular weight is 180.1359, as common compound, the synthetic route is as follows.

Oxalyl chloride (10 mL, 1 10 mmol) was added dropwise to a stirred suspension of 6- fluoroimidazo[1 ,2-a]pyridine-3-carboxylic acid (24b) (2 g, 1 1 mmol) and catalytic amounts of DMF in dichloromethane (20 mL). After 5 hours, the solvent was evaporated and the solid was suspended in dry DCE (20 mL) and added to a stirred solution of 3- amino-4-methylbenzonitrile (1 .45 g, 1 1 mmol) and DIEA (6 mmol) in DCE (1 0 mL) at 0 C. After the addition, the reaction was heated at 60 C for 5 hours. The mixture was subjected to standard aqueous work and silica purification to give N-(5-cyano-2- methylphenyl)-6-fluoroimidazo[1 ,2-a]pyridine-3-carboxamide (39) as a solid. 1 H NMR (400MHz, c/6-DMSO) delta 10.14 (s, 1 H), 9.45 (dd, J = 5.2, 2.0 Hz, 1 H), 8.62 (s, 1 H), 7.90 – 7.87 (m, 2 H), 7.68-7.63 (m, 1 H), 7.53 (d, J = 8.0 Hz, 1 H), 2.37 (s, 3H). MS m/z 295.1 (M+1 ) +.

Statistics shows that 1019021-85-2 is playing an increasingly important role. we look forward to future research findings about 6-Fluoroimidazo[1,2-a]pyridine-3-carboxylic acid.

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

Adding a certain compound to certain chemical reactions, such as: 69045-78-9, 2-Chloro-5-(trichloromethyl)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: 2-Chloro-5-(trichloromethyl)pyridine, blongs to pyridine-derivatives compound. Recommanded Product: 2-Chloro-5-(trichloromethyl)pyridine

2000 kg of 2-chloro-5-trichloromethylpyridine was placed in a glass-lined chlorination kettle.Then adding catalyst to the reactorThe 150kg reactor is heated with a heat transfer oil.When the temperature rises to 130 C, chlorine gas is introduced into the reactor to control the amount of chlorine.The reaction temperature was controlled at 180 C. The reaction time is usually 100 hours.After the reaction is completed, the temperature is lowered to 50 C, and the catalyst is filtered off.After the 2,3-dichloro-5-trichloromethylpyridine was metered, it was fluorinated in a fluorination kettle.

The synthetic route of 69045-78-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong Huimeng Biological Technology Co., Ltd.; Xiao Caigen; Liu Shuwen; (7 pag.)CN107935920; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 13362-30-6, 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 13362-30-6, name is Ethyl 2-aminoisonicotinate. This compound has unique chemical properties. The synthetic route is as follows.

[1- [5-CHLORO-2- (4-METHOXY-BENZYLOXY)-PHENYL]-PENTANE-1,] 4-dione (1.04g, 2. [9MMOL)] and 2- amino-isonicotinic acid ethyl ester (0.54g, 3. [2MMOL)] (Linschoten et [AL,] W00066557) were heated in toluene (0. 5ml) in a sealed vessel at [150C] for 12 hours. Upon cooling, the residue was purified by chromatography on silica gel with isohexane/EtOAc (15%) as eluant, to give the title compound (510mg, 36%). [1H] NMR [(400MHZ,] CDCl3) 1.31 (3H, t, J=7.5Hz), 2.29 (3H, s), 3.79 (3H, s), 4.29 (2H, q, J=7.5Hz), 4.59 (2H, s), 6.12 (1H, d, J=3.5Hz), 6.32 (1H, d, J=3.5Hz), 6.58 (1H, broad d, J=9Hz), 6.79 (2H, d, J=8.5Hz), 6.98 (2H, d, J=8.5Hz), 7.05 (1 H, dd, J=3,9Hz), 7.26 (1 H, d, under CDCI3), 7.40 (1 H, broad s), 7.66 (1 H, dd, J=1.5, 7Hz), 8.52 (1 H, d, J=7Hz). LC/MS t=4.01 min [MH+] 477/479

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 13362-30-6, Ethyl 2-aminoisonicotinate.

Reference:
Patent; GLAXO GROUP LIMITED; WO2003/101959; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 59020-10-9 ,Some common heterocyclic compound, 59020-10-9, molecular formula is C17H31NSn, 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 alcohol 348 (310 mg, 1.21 mmol), 3- (tributyl) stannylpyridine (446 mg, 1.21 mmol), Pd (DPPF) 2CL2 (59 mg, 0.072 mmol), copper (I) chloride (12 mg), lithium chloride (305 mg, 7.20 mmol) in DMSO (3.0 mL) was degassed by argon and then was stirred at 60C for 16 h. The reaction was quenched by the addition of H20 (50 mL), NH40H (0.2 mL), EtOAc (150 mL) and CH2C12 (20 mL). The mixture was passed through celite. The organic layer was washed with water (50 ML x 3), dried with NA2S04, and the residue was purified by flash- chromatography (eluant: MEOH/CH2CL2, 2/100), to give 488 (265 mg). Data for 488 : 1HNMR (300 MHz, CDC13) : 8 8.88 (s, 1H), 8.63 (d, J= 4 Hz, 1H), 7.92 (d, J= 8 Hz, 1H), 7.89 (d, J= 8 Hz, 2H), 7.64 (d, J= 8 Hz, 1H), 7.41 (dd, J= 8,5 Hz, 1H), 4.92 (dddd, J= 12,8, 3,3 Hz, 1H), 3.92 (dd, J= 12,3 Hz, 1H), 3.72 (dd, J= 12,5 Hz, 1H), 3.44 (dd, J= 17,11 Hz, 1H), 3. 33 (dd, J = 17,8 Hz, 1H).

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. 59020-10-9, 3-(Tributylstannyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RIB-X PHARMACEUTICALS, INC.; WO2004/29066; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 89282-03-1, 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. 89282-03-1, name is 3-Iodopyridin-4-ol, molecular formula is C5H4INO, 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.

3-Iodo-4-hydroxypyridine (0.500 g, 2.250 mmol) was reacted with allyl bromide (0.409 g, 3.380 mmol), potassium carbonate (0.780 g, 5.630 mmol) and potassium iodide (0.016 g, 0.100 mmol) in acetone (20 mL) at reflux temperature for 2 h. Then reaction mixture was cooled to room temperature, filtered and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexanes/ethyl acetate = 90/10) to get the title compound (0.400 g, 67%) as a liquid. LCMS: nt/z 261.9 [M+l] +; NMR (300 MHz, DMSO-d6) delta 7.86-7.85 (d, / =2.4Hz, 1H), 7.31-7.28 (m, 1H), 6.41-6.38 (d, / =7.2 Hz, 1H), 5.97-5.86 (m, 1H), 5.43-5.40 (dd, / =9.6, 1.5 Hz, 1H), 5.29-5.25 (dd, / = 10.8, 1.0 Hz, 1H), 4.40-4.38 (m, 2H).

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 89282-03-1, 3-Iodopyridin-4-ol.

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

Synthetic Route of 127446-34-8 , The common heterocyclic compound, 127446-34-8, name is N-(6-Chloro-3-formylpyridin-2-yl)pivalamide, molecular formula is C11H13ClN2O2, 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 : Sodium thiomethoxide (1 .37 g, 19.5 mmol, 1 .50 eq) is added to N-(6-chloro-3-formyl- pyridin-2-yl)-2,2-dimethyl-propionamide (Org Process Res. Dev. 2009, 13, 555) (1 .87 g, 7.79 mmol) in THF (50 mL) in a round-bottom flask and the solution is stirred at 50 C for 2 h. The reaction mixture is diluted with EtOAc and washed with brine. The organic layer is dried over MgS04, filtered and concentrated under reduced pressure to afford intermediate 5001 A.

The synthetic route of 127446-34-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FADER, Lee; LEPAGE, Olivier; BAILEY, Murray; BEAULIEU, Pierre Louis; BILODEAU, Francois; CARSON, Rebekah; GIROUX, Andre; GODBOUT, Cedrickx; MOREAU, Benoit; NAUD, Julie; PARISIEN, Mathieu; POIRIER, Martin; POIRIER, Maude; SURPRENANT, Simon; THIBEAULT, Carl; WO2013/152063; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 58539-65-4, 2-Methylnicotinamide, 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: 58539-65-4, blongs to pyridine-derivatives compound. Recommanded Product: 58539-65-4

Oxalyl chloride (1.90 mL, 21.8 mmol) was added to 2-methyl nicotinic acid (1.50 g, 10.9 mmol) in anhydrous dichloromethane (20 mL) with triethylamine (1.6 mL, 11.5 mmol) and the reaction mixture was kept at room temperature overnight before the solvent was removed. THF was added to the residue and ammonia gas was bubbled through for 2 h. The THF was removed and the residue was dissolved into methanol and water and the pH was adjusted to 10.0 with potassium carbonate. The mixture was concentrated. After column chromatography the desired amide was isolated (1.10 g, 73.8%).NaH (0.428 g, 10.7 mmol, 60% in mineral oil) was added to 4-hydroxy-3,5-dimethylbenzonitrile (1.50 g, 10 mmol) in anhydrous DMF (8 mL). Benzyl bromide (1.83 g, 10.7 mmol) was added and the reaction was kept at room temperature overnight. The reaction mixture was poured into water. The isolated solid was further washed with hexane to yield the desired ether building block (2.0 g, 84.3%). It was used in the next reaction without further purification. The above amide (0.65 g, 4.77 mmol) in anhydrous THF (15 mL) was added drop-wise to BuLi (7.5 mL, 1.60 M) at -20 C. The reaction mixture was kept at this temperature for 1 h and then the above ether building block (1.13 g, 4.77 mmol) in THF (20 mL) was added drop-wise at -20 C. and the reaction was stirred for 1.5 h. The reaction temperature was increased to room temperature and continued for a further 1 h. Water (20 mL) was added and the mixture was stirred for a while before the solvent was removed and the residue was purified by column chromatography to yield the desired intermediate (0.50 g, 29.4%). A 50 mL flask was charged with the above described intermediate (0.50 g, 0.0014 mol) and pyridine hydrogen chloride (2.4 g, 0.014 mol) and the mixture was heated to 180 C. for 1.5 h. The mixture was cooled and poured into methanol (4 mL), then filtered. The collected solid was further washed with ethyl acetate and dried to give 7-(4-hydroxy-3,5-dimethylphenyl)-1,6-naphthyridin-5(6H)-one (350 mg, 82.7%) as an HCl salt. Selected data: MS (ES) m/z: 266; MP>350 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,58539-65-4, 2-Methylnicotinamide, and friends who are interested can also refer to it.

Reference:
Patent; Wong, Norman C.W.; Tucker, Joseph E.L.; Hansen, Henrik C.; Chiacchia, Fabrizio S.; McCaffrey, David; US2008/188467; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem