Pyridine-derivatives

Application of 13362-78-2, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 13362-78-2 as follows.

A mixture of ZnSO4* 7H2O (0.05mmol, 0.010g), H2L (0.025mmol ,0.006g), DPE (0.025mmol 0.005g), NaOH (0.025mmol,0.001g) and H2O (8mL) was sealed in a Teflon-lined autoclave and heated at 120 °C for 3 days,then followed by slow cooling to room temperature. The yield of the colorless block crystals is ca.68percent based on H2L. Elemental Anal. Found:C, 55.8;H,3.5;N,8.1percent. Calcd. for ZnC25H21N3O7: C,55.5;H,3.9;N,7.8percent. IR(cm1) (seeFig.S1): 3325(s),3061(m),1637(s),1568(s),1418(m),1387(s),1336(m),1281(m),1194(s),1148(w),1037(m),1017(m),964(m),842(s),769(m),671(m),549(s),462(m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13362-78-2, its application will become more common.

Reference:
Article; Yan, Xingxiu; Qiu, Xiandeng; Yan, Zhishuo; Li, Hongjiang; Gong, Yun; Lin, Jianhua; Journal of Solid State Chemistry; vol. 237; (2016); p. 313 – 322;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 889676-37-3 ,Some common heterocyclic compound, 889676-37-3, molecular formula is C6H5BrN2O, 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 1-11: tert-Butyl 6-r5-carbamoylpyridin-2-ylV4-oxospirorchroman-2,4′-pirhoeridmel-r-carboxylatel’-tert-butoxycarbonyl-6-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)spiro[chroman-2,4′-piperidm]-4-one (40.0 g, 90.0 mmol), 6-chloronicotinamide (17.0 g, 108 mmol), Pd(PPh3)4 (5.21 g, 4.51 mmol), and aqueous 2M Na2CO3 (100 ml) solution were suspended in dioxane (300 ml) and heated at 100C for 16 h. The reaction mixture was diluted with CEtaCI3 and H2O, the aqueous layer was extracted with CHCI3. The combined organic layer was washed with brine, dried over MgSCvj. and silicagel. The desiccant was removed through celite filtration and the filtrate was concentrated under reduced pressure. The resulting residue was purified by crystallization (CHCI3 -EtOAc) to obtain the intended compound as a colorless solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,889676-37-3, its application will become more common.

Reference:
Patent; BANYU PHARMACEUTICAL CO.,LTD.; JONA, Hideki; SHIBATA, Yoshihiro; YAMAKAWA, Takeru; WO2010/2010; (2010); 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.1210419-26-3, name is Methyl 6-bromo-5-fluoropicolinate, molecular formula is C7H5BrFNO2, molecular weight is 234.02, as common compound, the synthetic route is as follows.Formula: C7H5BrFNO2

Intermediate 19-5 5-Fluoro-6-(1-methyl-1H-pyrazol-4-yl)pyridine-2-carboxylic acid (1369) (1370) 500 mg of methyl 6-bromo-5-fluoropyridine-2-carboxylate were reacted analogously with 533 mg (1.2 equiv.) of 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole in the microwave at 120 C. for 90 min. This gave 380 mg (80% of theory) of the title compound as a crude product. (1371) UPLC-MS (Method A1): Rt=0.72 min (1372) MS (ESIpos): m/z=222 (M+H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1210419-26-3, Methyl 6-bromo-5-fluoropicolinate, and friends who are interested can also refer to it.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; BOTHE, Ulrich; SIEBENEICHER, Holger; SCHMIDT, Nicole; ROTGERI, Andrea; BOeMER, Ulf; RING, Sven; IRLBACHER, Horst; GUeNTHER, Judith; STEUBER, Holger; LANGE, Martin; SCHAeFER, Martina; (191 pag.)US2016/311833; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 55314-16-4 , The common heterocyclic compound, 55314-16-4, name is 1-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one, molecular formula is C10H12N2O, 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.

3- [(Aminoiminomethyl)amino] -4-methyl-benzoic acid methylester mononitrate (10 g),3-(Dimethylamino)-1-(pyridine-3-yl)prop-2-en-1-one (7.3 g), sodium hydroxide (1.7 g) was added to 1-butanol (100 mL) in a round bottom flask under nitrogen atmosphere. The reaction mass was heated to reflux temperature and stirred for 12 his. Then the reaction mass was cooled to 25-35C and iN sodium hydroxide solution (1.5 g in 37 mLof DM wter) was added to it over a period of 20 mm. The reaction mass was heated to reflux temperature (120-125C) and then cooled to 25-35C. iN hydrochloric acid. (3.3 mL in 37 mL of DM water) was added to the reaction mass at 25-35C and stirred for an hour. The material formed was filtred, washed with DM water? and then dried under vacuum at 50-55C to provide the title compound (8.7 g).

The synthetic route of 55314-16-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LAURUS LABS PRIVATE LIMITED; CHAVA, Satyanarayana; GORANTLA, Seeta Rama Anjaneyulu; INDUKURI, Venkata Sunil Kumar; MOTURU, Venkata Rama Krishna Murthy; JAMJANAM, Srivardhana Rao; SELA, Venkata Purushottama Siva Prasad; WO2015/87343; (2015); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 39890-95-4 , The common heterocyclic compound, 39890-95-4, name is 2-Chloro-6-(trifluoromethyl)pyridine, molecular formula is C6H3ClF3N, 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 solution of 2-chloro-6-(trifluoromethyl)pyridine (1.0 g, 5.5 mmol), piperazine (1.4 g, 16.0 mmol), and triethylamine (1.5 mL, 11.0 mmol) were mixed in DMF (10 mL) in a dealed tube. The mixture was heated at 100 C. overnight. The reaction mixture was concentrated and chromatographed on silica gel (ethyl acetate to EA/MeOH/Et3N=9:1:0.5) to give 1.05 g of the desired product. MS calculated for C10H12F3N3: (M+H) 232.1; found 232.1.

The synthetic route of 39890-95-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xue, Chu-Biao; Zheng, Changsheng; Feng, Hao; Xia, Michael; Glenn, Joseph; Cao, Ganfeng.; Metcalf, Brian W.; US2006/4018; (2006); 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. 934758-27-7, name is 2-Amino-6-bromopyridin-3-ol, the common compound, a new synthetic route is introduced below. Quality Control of 2-Amino-6-bromopyridin-3-ol

A solution of 2-amino-6-bromopyridin-3-ol (500 mg, 2.29 mmol) in DMF (5 mL) was treated with potassium carbonate (367.5 mg, 2.66 mmol). 2-Bromo-2,2-difluoro- acetyl chloride (566 mg, 2.93 mmol) was added dropwise over 10 minutes with cooling in an ice-water bath. The reaction mixture was warmed to room temperature over 3 h, then heated at 50C for 18 h. The resulting mixture was concentrated under reduced pressure, then EtOAc (5 mL) and water (5 mL) were added. The organic layer was separated and washed with 2M aqueous HC1 (5 mL), saturated aqueous NaHC03 solution and brine, then dried (MgSC^). The crude material was concentrated under reduced pressure. (0855) Trituration of the resulting brown oil with DCM afforded the title compound (180 mg, 26%) as an orange solid. Method B HPLC-MS: MH+ mlz 264/266, RT 1.91 minutes (100%)

The synthetic route of 934758-27-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UCB BIOPHARMA SPRL; BRACE, Gareth Neil; CHOVATIA, Prafulkumar Tulshibhai; FOULKES, Gregory; JOHNSON, James Andrew; JONES, Severine Danielle; KROEPLIEN, Boris; LECOMTE, Fabien Claude; LOKE, Pui Leng; LOWE, Martin Alexander; MANDAL, Ajay; NORMAN, Timothy John; PALMER, Christopher Francis; PEREZ-FUERTES, Yolanda; PORTER, John Robert; SMYTH, Donald; TRANI, Giancarlo; UDDIN, Muhammed; ZHU, Zhaoning; (207 pag.)WO2016/198400; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 407-20-5 ,Some common heterocyclic compound, 407-20-5, molecular formula is C5H3BrFN, 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.

To a stirred solution of diisopropylamine (0.48 mL, 0.0034 mol) in dry tetrahydrofuran (10 mL) was added 1.6 M rc-butyl lithium in hexane (2.39 mL, 0.00369 mol) drop wise under nitrogen atmosphere at -78 C and stirred for 30 min at -78 C. To the above stirred mixture was added a solution of 3-bromo-5-fiuoropyridine (0.5 g, 0.00284 mol) in dry tetrahydrofuran at -78 C and stirred for 45 min. After 45 min, a solution of hexachloroethane in dry tetrahydrofuran was added to the above reaction mixture at -78 C and stirred for 30 min at -78 C. The reaction mixture was slowly warmed to RT and stirred for 1 h. The reaction was quenched with saturated solution of ammonium chloride (10 mL) and extracted with diethyl ether (25 mL x 3). The combined organic layer was washed with water, saturated aqueous sodium chloride solution, dried over anhydrous sodium sulphate and evaporated. The obtained crude was purified with silica gel chromatography by hexane to afford the title compound. lH NMR (400 MHz,CDC13) delta: 8.58 (s, 1 H), 8.43 (s, 1 H). MS (M+l): 209.9.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,407-20-5, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ElexoPharm GmbH; HOYT, Scott, B.; PETRILLI, Whitney Lane; LONDON, Clare; XIONG, Yusheng; TAYLOR, Jerry Andrew; ALI, Amjad; LO, Michael; HENDERSON, Timothy, J.; HU, Qingzhong; HARTMANN, Rolf; YIN, Lina; HEIM, Ralf; BEY, Emmanuel; SAXENA, Rohit; SAMANTA, Swapan Kumar; KULKARNI, Bheemashankar, A.; WO2012/148808; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1462-86-8, 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.1462-86-8, name is 3-Aminopicolinic acid, molecular formula is C6H6N2O2, molecular weight is 138.12, as common compound, the synthetic route is as follows.

Step B. 2-(I-Naphthalenyl)-H-pyrido[3,2-d][1,3]oxazin-4-one; 1-Naphthalenecarbonyl chloride (400 mg, 2.1 mmol) in CH2C12 (2 mL) was added into a solution of 3-amino-2-pyridinecarboxylic acid (277 mg , 2.0 mmol) and diisopropylethylamine (284 mg, 2.2 mmol) in DMF (10 mL) at 0 C. The reaction mixture was allowed to stir overnight at room temperature, and was then treated with diisopropylethylamine (284 mg, 2.2 mmol) and HATU (837 g, 2.2 mmol). After stirring for 1 h at room temperature, the reaction mixture was heated at 50 C to provide the title compound which was used in Step A. MS (ESI) (M+H)+ 274.79

Statistics shows that 1462-86-8 is playing an increasingly important role. we look forward to future research findings about 3-Aminopicolinic acid.

Reference:
Patent; AstraZeneca AB; WO2005/115987; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 571189-49-6 ,Some common heterocyclic compound, 571189-49-6, molecular formula is C10H16N4, 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.

To Compound 50 0.060 g (0.205 mmole) was added 5-(4-methylpiperazin-1-yl)pyridin- 2-amine (35.42 mg, 0.9 eq) followed by the addition of 1,4-dioxane (3 mL). After degassing with nitrogen, Pd2dba3 (12 mg), BINAP (16 mg) and sodium tert-butoxide (24 mg) were added.The contents were then heated at 90 degrees in a CEM Discovery microwave for 3 hrs. Thereaction was then loaded onto a silica gel column and purified by eluting with DCM/MeOH (0-15%). ?HNMR (600 MHz, DMSO-d6) oe ppm 0.75 (t, J7.47 Hz, 3 H) 0.91 (d, J6.73 Hz, 3 H)1.04 – 1.20 (m, 2 H) 1.80 – 1.98 (m, 1 H) 2.77 (d, J=3.81 Hz, 3 H) 2.94 – 3.90 (m, 10 H) 4.54 -4.68 (m, 1 H) 7.06 – 7.23 (m, 2 H) 7.56 – 7.75 (m, 1 H) 7.90 – 8.12 (m, 2 H) 8.29 (s, 1 H) 9.07 (s,1 H) 10.98- 11.74(m,2H). LCMS(ESI)435(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. 571189-49-6, 5-(4-Methylpiperazin-1-yl)pyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; G1 THERAPEUTICS, INC.; STRUM, Jay, Copeland; BISI, John, Emerson; ROBERTS, Patrick, Joseph; SORRENTINO, Jessica, Ann; (304 pag.)WO2016/40848; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1620-72-0, 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 1620-72-0, name is 2-Methyl-6-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

2-methyl-6-(trifluoromethyl)pyridine (100 mg, 0.620 mmol) was dissolved in CC14 (3 mL), and N-bromosuccinimide (NBS) (110 mg, 0.620 mmol) and 1,1′- azobis(cyclohexanecarbonitrile) (VAZO, 8 mg, 0.031 mmol) were added thereto, followed by heating and stirring at 90 C for 15 hrs. The reaction solution was filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by MPLC (Hex/EA = 5:1) to obtain the title compound as white solid (42.5 mg, yield: 28.4%). 1H NMR (300MHz, CDC13) delta 4.60 (2H, s), 7.61 (1H, d), 7.68 (1H, d), 7.90 (1H, t)

According to the analysis of related databases, 1620-72-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SK CHEMICALS CO., LTD.; KIM, Seon-Mi; KIM, Jae-Sun; LEE, Minhee; LEE, So-Young; LEE, Bong-Yong; SHIN, Young Ah; PARK, Euisun; LEE, Jung A; HAN, Min-Young; AHN, Jaeseung; YOO, Taekyung; KIM, Hun-Taek; WO2013/129879; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem