Category: pyridine-derivatives

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 159981-19-8, name is 6-(2,2,2-Trifluoroethoxy)nicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 6-(2,2,2-Trifluoroethoxy)nicotinaldehyde

Step 1 – Synthesis of[5-(5-chloro-lH-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-yl]-[6-(2,2,2- trifluoro-ethoxy)-pyridin-3-ylmethyl]-amine (P-0409):; [0254] To 5-(l -benzenesulfonyl-5-chloro-lH-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2- ylamine (599, 124.1 mg, 0.31 mmol, prepared as described in Example 29, Scheme 185) in ethanol (3.00 mL) and acetic acid (0.2 mL) were added 6-(2,2,2-trifluoro-ethoxy)-pyridine-3- carbaldehyde (603, 164.0 mg, 0.80 mmol) and silica supported cyanoborohydride (1.21 mmol/g, 0.700 g). The reaction was irradiated with microwave on 300 watts, 1000C for 150 minutes. To the reaction was added a solution of potassium hydroxide (9.0 M in water, 1.0 mL). The reaction was irradiated with microwave on 300 watts, 100 0C for 10 minutes. The reaction was poured into aqueous potassium carbonate and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 20% to 100% ethyl acetate in hexane to give the desired compound (P-0409, 10.6 mg, 7.6%). MS ESI) [M+H+]+ = 448.4.

With the rapid development of chemical substances, we look forward to future research findings about 159981-19-8.

Reference:
Patent; PLEXXIKON, INC.; WO2008/63888; (2008); A2;,
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. 56026-36-9, name is Methyl 6-(hydroxymethyl)nicotinate, molecular formula is C8H9NO3, 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. Application In Synthesis of Methyl 6-(hydroxymethyl)nicotinate

A mixture of methyl 6-(hydroxymethyl)nicotinate (7 g , 37 mmol) and Mn02 (32,3 g , 372 mmol) in DCM ( 200 mL ) was stirred at 20 C for 4 hours. The mixture was filtered and the filtrate was concentrated. The residue was purified by column chromatography on silica gel (PE/EtOAc = 5/1) to afford methyl 6-formylnicotinate (6 g , 97%).MS-ESI (m/z): 166.2 (M+l) + (LC-MS method C; Ret. time: 0.36 min).

With the rapid development of chemical substances, we look forward to future research findings about 56026-36-9.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WU, Hao; KIM, Ronald M.; LIU, Jian; GAO, Xiaolei; BOGA, Sobhana Babu; GUIADEEN, Deodialsingh; KOZLOWSKI, Joseph; YU, Wensheng; ANAND, Rajan; YU, Younong; SELYUTIN, Oleg B.; GAO, Ying-Duo; LIU, Shilan; YANG, Chundao; WANG, Hongjian; WO2014/114185; (2014); 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. 152460-09-8, name is N-(2-Methyl-5-nitrophenyl)-4-(pyridin-3-yl)pyrimidin-2-amine. A new synthetic method of this compound is introduced below., Quality Control of N-(2-Methyl-5-nitrophenyl)-4-(pyridin-3-yl)pyrimidin-2-amine

170 L of Cone. Hydrochloric acid is charged into the reactor. 70 Kg of stannous chloride dihydrate is charged. Stirred for 10 minutes. Cooled the reaction mass to 0-5C. Added compound of the formula (VI) slowly during 3-4 hours at 0-5 C. reaction mass is brought to 25-35C. Maintained 1 V2 hour at 25-35C. Charged 500 Its of DM water to the reaction mass and charged slowly 400 L of 50% sodium hydroxide solution at 25-3 5C. Reaction mass is extracted with 2 x 250 L chloroform. The chloroform layer is water wash thoroughly and carbon treatment is given . Distilled off chloroform completely under vacuum and charged 20 L ethyl acetate. Cooled to 0-10C. Maintained 1 hour at 0-10C. Centrifuged and washed with 10 L ethyl acetate to provide N-(5-amino-2-methyl phenyl)-4-(3-pyridyl)-2-pyrimidineamine of the formula [VII]Yield: 10 Kg (61.5%)MR: 141-144C.PuritybyHPLC:99.8%.Step -3:The preparation of N-(5-amino-2-methyl phenyl)-4-(3-pyridyl)-2-pyrimidineamine (VII)20 L of Cone. Hydrochloric acid is charged into the reactor. 7 Kg of stannous chloridedihydrate is charged. Stirred for 10 minutes. Cooled the reaction mass to 0-5C. Addedcompound of the formula (VI) slowly during 2-3 hours at 0-5C. reaction mass is broughtto 25-35C. Maintained 3 hours at 25-35C. Charged 500 Its of DM water to thereaction mass and charged slowly 40 L of 50% sodium hydroxide solution at 25-35C.Reaction mass is extracted with 2 x 35 L chloroform. The chloroform layer is waterwash thoroughly and carbon treatment is given . Distilled off chloroform completelyunder vacuum and charged 2 L ethyl acetate. Cooled to 0-10C. Maintained 1 hour at 0-10C. Centrifuged and washed with 1 L ethyl acetate to provide N-(5-amino-2-methylphenyi)-4-(3-pyridyl)-2-pyrimidineamine of the formula [VII]Yield: 0.98Kg(60%)MR: 140-143C.Purity by HPLC: 99.8%.Step -3: The preparation of N-(5-amino-2-methyl phenyl)-4-(3-pyridyl)-2-pyrimidineamine of theformula [VH] 17 L of Cone. Hydrochloric acid is charged into the reactor. 7 Kg of stannous chloride dihydrate is charged. Stirred for 10 minutes. Cooled the reaction mass to 0-5C. Added compound of the formula (VI) slowly during 2-3 hours at 0-5C. reaction mass is brought to 25-35C. Maintained 3 hours at 25-35C. Charged 500 Its of DM water to the reaction mass and charged slowly 40 L of 50% sodium hydroxide solution at 25-35C. Reaction mass is extracted with 2 x 50 L chloroform. The chloroform layer is waterwash thoroughly and carbon treatment is given . Distilled off chloroform completelyunder vacuum and charged 2 L ethyl acetate. Cooled to 0-10C. Maintainedl hour at 0-10C. Centrifuged and washed with 1 L ethyl acetate to provide N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine of the formula [VII]Yield : 0.97 Kg (60%)MR: 140-143C.Purity by HPLC: 99.7%. Step -3 ;The preparation of N-(5-amino-2-methyl phenyl)-4-(3-pyridyl)-2-pyrimidineamine of theformula [VII]19 L of Cone. Hydrochloric acid is charged into the reactor. 7 Kg of stannous chloridedihydrate is charged. Stirred for 10 minutes. Cooled the reaction mass to 0-5C. Addedcompound of the formula (VI) slowly during 2-3 hours at 0-5C. reaction mass is broughtto 25-35C. Maintained 2 1A hour at 25-35C. Charged 500 Its of DM water to thereaction mass and charged slowly 40 L of 50% sodium hydroxide solution at 25-35C.Reaction mass is extracted with 2 x 50 L chloroform. The chloroform layer is waterwash thoroughly and carbon treatment is given . Distilled off chloroform completelyunder vacuum and charged 2 L ethyl acetate. Cooled to 0-10C. Maintained 1 hour at 0-10C. Centrifuged and washed with 1 L ethyl acetate to provide N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine of the formula [VII]Yield: 1.05 Kg (64.5%)MR: 142-144C.Purity by HPLC: 99.85%.

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, 152460-09-8, N-(2-Methyl-5-nitrophenyl)-4-(pyridin-3-yl)pyrimidin-2-amine.

Reference:
Patent; NATCO PHARMA LIMITED; KOMPELLA, Amala; BHUJANGA RAO, Adibhatla, Kali, Sathya; VENKAIAH CHOWDARY, Nannapaneni; WO2004/108699; (2004); 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.102368-13-8, name is 1,1′-Thiocarbonylbis(pyridin-2(1H)-one), molecular formula is C11H8N2O2S, molecular weight is 232.2584, as common compound, the synthetic route is as follows.HPLC of Formula: C11H8N2O2S

Steps b, c : N-((cis)-3-isothiocyanatocyclobutyl)-3-(4-methoxyphenyl)bicyclo[1.1.1]pentane-1-carboxamide. A similar procedure to that described for the synthesis of N-(cis-(3-isothiocyanatocyclobutyl))-5-methoxy-[2,3′-bipyridine]-6′-carboxamide step c) and step d) was followed by using tert-butyl((cis)-3-(3-(4-methoxyphenyl)bicyclo[1.1.1]pentane1carboxamido) cyclobutyl) carbamate (58.0 mg, 0.15 mmol) to produce N-((cis)-3-isothiocyanatocyclobutyl)-3-(4-methoxyphenyl)bicyclo[1.1.1]pentane-1-carboxamide (26.0 mg, 52%). 1H NMR (400 MHz, CDCl3): delta 7.14 (d, J=8.0 Hz, 2H); 6.67 (brs, 1H); 5.75-5.63 (brs, 1H); 4.25-4.13 (m, 1H); 3.90-3.81 (m, 1H); 3.80 (s, 3H); 2.95-2.70 (m, 2H); 2.25 (s, 6H); 2.24-2.15 (m, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,102368-13-8, 1,1′-Thiocarbonylbis(pyridin-2(1H)-one), and friends who are interested can also refer to it.

Reference:
Patent; Northeastern University; Malamas, Michael S.; Makriyannis, Alexandros; Farah, Shrouq I.; Zvonok, Alexander M.; Alapafuja, Shakiru Olajire; (47 pag.)US2019/345132; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 931105-37-2, 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 931105-37-2, name is Methyl 5-bromo-2-fluoronicotinate. This compound has unique chemical properties. The synthetic route is as follows.

To an oven-dried 10 mL vial were added methyl 5-bromo-2-fluoronicotinate (1 g, 4.27 mmol), bis(pinacolato)diboron (217 mg, 0.854 mmol) and potassium acetate (1.258 g, 12.82 mmol). 1,4-Dioxane (20 mL) was introduced into the vial and nitrogen gas was blown through for 10 min. PdCl2(dppf) (0.156 g, 0.214 mmol) was added to the reaction mixture and degassing continued for 10 min. The mixture was heated to reflux at 80 C ON. The reaction mixture was filtered through a pad of Celite to remove the catalyst, and the filter cake was washed with EtOAc twice. The obtained organic solutions were concentrated. The crude residue was purified by flash column chromatography (ISCO, 80 g silica gel column, 20-50% EtOAc/hexanes) to yield methyl 2-fluoro-5-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate (1 g, 3.56 mmol, 83 %) as a white solid. MS ESI m/z 200.0 (M+H for the boronic acid)

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 931105-37-2, Methyl 5-bromo-2-fluoronicotinate.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WATTERSON, Scott Hunter; ANDAPPAN MURUGAIAH SUBBAIAH, Murugaiah; DZIERBA, Carolyn Diane; GONG, Hua; GUERNON, Jason M.; GUO, Junqing; HART, Amy C.; LUO, Guanglin; MACOR, John E.; PITTS, William J.; SHI, Jianliang; VENABLES, Brian Lee; WEIGELT, Carolyn A.; WU, Yong-Jin; ZHENG, Zhizhen Barbara; SIT, Sing-Yuen; CHEN, Jie; (810 pag.)WO2019/147782; (2019); 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. 71702-01-7, name is 5-Bromo-6-chloronicotinonitrile. A new synthetic method of this compound is introduced below., Computed Properties of C6H2BrClN2

Step 5; 3-Bromo-4- (3-bromo-5-cyano-pyridin-2-yloxy)-benzyl]- (3-methyl-butyl)-carbamic acid tert-butyl ester; Heat a mixture of the phenol obtained in step 4 (677 mg, 1.82 mmol), 5-Bromo-6-chloro- nicotinonitrile (395 mg, 1.82 mmol), K2CO3 (277 mg, 2.0 mmol) and DMF (22 mL) at 100C under N2 atmosphere overnight. Cool at room temperature. Pour into ice-water and extract with EtOAc. Dry the organic layer over Na2SO4. Eliminate the solvent. Purify by flash chromatography on silica gel (eluent : hexane/EtOAc 8/1) to afford the title compound (860 mg, 85%). H-NMR (CDCl3, 300 MHz): 8.30 (d, 1H, J= 2.0 Hz), 8.19 (d, 1H, J= 2.0 Hz), 7.53 (s, 1H), 7.29 (m, 1H), 7.18 (d, 1H, J= 8.3 Hz), 4.43 (m, 2H), 3.19 (m, 2H), 1.58-1. 42 (m, 12H), 0.90 (d, 6H, J= 6.5 Hz).

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, 71702-01-7, 5-Bromo-6-chloronicotinonitrile.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/90337; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 5349-17-7, 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 5349-17-7, name is 2-Bromo-1-(pyridin-4-yl)ethanone hydrobromide. This compound has unique chemical properties. The synthetic route is as follows.

Example 136: 4-(4-Pyridin-4-yl-thiazol-2-ylmethoxy)piperidine-1-carboxylic acid tert-butyl ester A solution of 2-bromo-1-pyridin-4-yl-ethanone hydrobromide (35mg, 124mol) and 4- thiocarbamoylmethoxypiperidine-1-carboxylic acid tert-butyl ester (Preparation 18,34mg, 124Rmol) in methanol (2ml) was heated at 60C for 1. 5h. The reaction mixture was diluted with EtOAc (60ml), washed with saturated aqueous NaHCO3 (15ml) and brine (15ml) then dried (MgSO4). The solvent was removed and the residue purified by flash chromatography (EtOAc) to afford the title compound: RT = 2.95min, mlz (ES+) = 376.1 [M+H] +.

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 5349-17-7, 2-Bromo-1-(pyridin-4-yl)ethanone hydrobromide.

Reference:
Patent; PROSIDION LIMITED; WO2005/61489; (2005); 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. 1628-89-3, name is 2-Methoxypyridine, molecular formula is C6H7NO, 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. Formula: C6H7NO

A flame-dried, 20 ml argon-filled Schlenk-tube was charged with 2-methoxypyridine (15) (55 mg, 0.50 mmol, 1 .0 equiv.), and dry MeCN (2.0 ml, c = 0.25 M). Trifluoroacetic anhydride (0.21 ml, 0.32 g, 1.5 mmol, 3.0 equiv.) was added while stirring the reaction mixture. After cooling to 0 C, tetrafluorothianthrene reagent (97 % (w/w) tetrafluorothianthrene-S-oxide 1 , 3 % (w/w) tetrafluorothianthrene 2, 157 mg, 0.50 mmol, 1 .0 equiv.) was added in one portion, followed by the addition of trimethylsilyl-trifluormethanesulfonate (181 pi, 0.22 g, 1.0 mmol, 2.0 equiv.) in one portion at 0 C, leading to a dark suspension. The vial was sealed and the mixture was stirred at 0 C for 1 h, followed by stirring at 25 C for 1 h. The reaction mixture was concentrated under reduced pressure, and diluted with 5 ml DCM. The DCM phase was poured onto a saturated aqueous NaHC03solution (ca. 10 ml). The mixture was poured into a separatory funnel, and the layers were separated. The DCM layer was washed with aqueous NaBF4solution (2 x ca. 10 ml, 5 % w/w), and with water (2 x ca. 10 ml). The DCM layer was dried over Na2S04, filtered, and the solvent was removed under reduced pressure. The residue was purified by chromatography on silica gel eluting with DCM / /-PrOH, (30:1 (v/v)). The product was dissolved in 5 ml DCM, and precipitated with 20 ml Et20. The precipitate was dried in vacuo to afford 21 1 mg (87 %) of 15a as colorless solid.NMR Spectroscopy:1H NMR (500 MHz, CD3CN, 298 K, d): 8.35 (dd, J = 9.1 Hz, 7.2 Hz, 2H), 8.06 (dd, J = 2.9 Hz, 0.5 Hz, 1 H), 7.97 (dd, J = 9.9 Hz, 7.1 Hz, 2H), 7.54 (dd, J = 9.2 Hz, 2.9 Hz, 1 H), 6.91 (dd, J = 9.2, 0.6 Hz, 1 H), 3.93 (s, 3H).13C {1H} NMR (128 MHz, CD3CN, 298 K, d): 168.1 , 154.8 (dd, J = 261.6 Hz, 13.1 Hz), 151 .7 (dd, J = 155.6 Hz, 13.7 Hz), 149.5, 139.6, 134.9 (dd, J = 8.8 Hz, 4.0 Hz), 125.0 (dd, J = 22.3 Hz, 2.4 Hz), 121.3 (d, J = 21 .9 Hz), 1 15.5 (dd, J = 7.2 Hz, 3.6 Hz), 1 14.2, 1 12.1 , 55.5. 19F {1H} NMR (471 MHz, CD3CN, 298 K, d): -125.6 (d, J = 20.4 Hz), -133.6 (d, J = 20.4 Hz), -151 .1 (bs), -151.1 (bs).HRMS-ESI(m/z) calc?d for CI8H10F4NOS2+[M-BF4]+, 396.013700; found, 396.013448; deviation: 0.6 ppm.

With the rapid development of chemical substances, we look forward to future research findings about 1628-89-3.

Reference:
Patent; STUDIENGESELLSCHAFT KOHLE MBH; RITTER, Tobias; BERGER, Florian; (146 pag.)WO2020/94673; (2020); 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 585-48-8, name is 2,6-Di-tert-butylpyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 585-48-8

Example 26 5-(S)-Acetamidomethyl-3-[4′-formamido-3′-fluorophenyl]oxazolidine-2-one A solution of 5-(S)-acetamidomethyl-3-[4′-amino-3′-fluorophenyl]-oxazolidine-2-one (0.200 g, 0.748 mmol), p-nitrophenyl formate (0.188 g, 1.12 mmol), and 2,6-di-(tert-butyl)pyridine (0.336 mL, 1.50 mmol) in THF (4 mL) was stirred at 65 C. overnight. Solvent was removed under vacuum and the residue purified by PTLC (30% acetone in DCM) to give product as a white solid (0.188 g, 85%). M.p. 196-8 C.; MS (m/z): [M+H]+=296.

With the rapid development of chemical substances, we look forward to future research findings about 585-48-8.

Reference:
Patent; Pharmacia & Upjohn Company; US6441005; (2002); B1;,
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. 96530-75-5, name is 4-Fluoropyridin-2(1H)-one. A new synthetic method of this compound is introduced below., category: pyridine-derivatives

Into a 25 mL round-bottom flask were added tert-butyl (3R)-3-ethylpiperazine-1- carboxylate(200 mg, 0.93 mmol, 1 equiv.) and 4-fluoro-1,2-dihydropyridin-2-one (126.6 mg, 1.12 mmol, 1.20 equiv.) at room temperature. The resulting mixture was stirred for 4 h at 120 degrees C under nitrogen atmosphere. The reaction was monitored by LCMS. The mixture was allowed to cool down to room temperature. The residue was purified by reverse phase flash with the following conditions (Column: XBridge Prep C18 OBD Column 19×150mm 5um; Mobile Phase A: Water(5mmol/L CH3COOH), Mobile Phase B: ACN; Flow rate: 20 mL/min; Gradient: 30% B to 40% B in 10 min; 254/220 nm; Rt: 5.18 min) to afford tert-butyl (3R)-3-ethyl-4-(2- oxo-1,2-dihydropyridin-4-yl)piperazine-1-carboxylate(120 mg, 41.83%) as a yellow solid

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, 96530-75-5, 4-Fluoropyridin-2(1H)-one.

Reference:
Patent; GOLDFINCH BIO, INC.; YU, Maolin; DANIELS, Matthew, H.; HARMANGE, Jean-christophe, P.; TIBBITTS, Thomas, T.; LEDEBOER, Mark, W.; WALSH, Liron; MUNDEL, Peter, H.; MALOJCIC, Goran; (860 pag.)WO2019/55966; (2019); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem