Category: pyridine-derivatives

Reference of 38186-84-4, 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. 38186-84-4, name is 2-Chloro-5-fluoro-3-picoline, molecular formula is C6H5ClFN, 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 2-chloro-5-fluoro-3-methylpyridine D38 (0.50 g, 2.82 mmol) in dry toluene (12.5 ml) were added sodium t-butoxyde (0.462 g, 4.81 mmol), Pd2(dba)3 (0.315 g, 0.344 mmol), BINAP (0.642 g, 1.031 mmol) and benzophenone imine (0.692 ml, 4.12 mmol). The resulting mixture was degassed (3×pump/N2) and then heated to 80 C. After 1 h stirring, the mixture was cooled down to room temperature, diluted with Et2O (400 ml) and filtered through a celite pad. Volatiles were evaporated, the resulting oil was dissolved in THF (34 ml) and HCl (1.408 ml of a 2 M aqueous solution, 2.82 mmol) was added. The mixture was stirred at room temperature for 1.5 h, then neutralized with a saturated NaHCO3 aqueous solution and diluted with DCM (200 ml). The inorganic layer was back-extracted with DCM (2×50 ml). The collected organic layers were dried (Na2SO4), filtered and evaporated. The residue was purified by flash chromatography on silica gel (Biotage SP4 12M, Cy/EtOAc 60/40). Collected fractions gave the title compound D39 (0.20 g, 1.554 mmol, 55.2% yield from D38, two steps), as an orange solid. MS: (ES/+) m/z: 127 (M+1). C6H7FN2 requires 126.1H NMR (400 MHz, DMSO-d6) delta(ppm): 7.73 (d, 1H), 7.23 (dd, 1H), 5.60 (bs, 2H), 2.04 (s, 3H).

According to the analysis of related databases, 38186-84-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALVARO, GIUSEPPE; AMANTINI, DAVID; BELVEDERE, SANDRO; US2009/22670; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 6515-09-9, 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. 6515-09-9, name is 2,3,6-Trichloropyridine. A new synthetic method of this compound is introduced below.

General procedure: Complex (1 .71 mol%) and 3 mL of stock solution (made from 3.333g TCP A in IPA 30 mL) are added to each reactor, followed by NEt3 (446 pL). The reactors are purged with nitrogen (3 times) and hydrogen (3 times) then hydrogenated at 0.5 MPa and 85 C for 180 mm in a Biotage Endeavor. 40 pL aliquot of each reaction mixture is added to 1 mL MeCN and analysed by normal HPLC method.HPLC areas are converted to concentration (pmol/mL) from the gradients equations in the multipoint external standard.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6515-09-9, 2,3,6-Trichloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; JOHNSON MATTHEY PUBLIC LIMITED COMPANY; MORTIMER, Danny Lee; (19 pag.)WO2017/85476; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 40473-07-2 ,Some common heterocyclic compound, 40473-07-2, molecular formula is C6H6BrNO, 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.

General procedure: The aryl halide was dissolved in 5mL of methanol per mmol of (hetero)arylhalide, magnesium (5 equiv.) added and the mixture was stirred at room temperature. After completion of the reaction (between 6-12h), the reaction mixture was poured into water, acidified with dilute HCl, and extracted with ethyl acetate. The organic phase was dried over MgSO4 and concentrated under reduced pressure. The product was purified if necessary by column chromatography on silica gel.

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. 40473-07-2, 2-Bromo-6-methoxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Jouha, Jabrane; Khouili, Mostafa; Hiebel, Marie-Aude; Guillaumet, Gerald; Suzenet, Franck; Tetrahedron Letters; vol. 59; 32; (2018); p. 3108 – 3111;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 100397-96-4 ,Some common heterocyclic compound, 100397-96-4, molecular formula is C13H10BrNO, 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.

2) (E)-1-(4-bromophenyl)-3-(dimethylamino)-2-(pyridin-4-yl)prop-2-en-1-one A mixture of 1-(4-bromophenyl)-2-(pyridin-4-yl)ethanone (500 mg, 1.811 mmol) and 1,1-dimethoxy-N,N-dimethylmethanamine (1 g, 8.39 mmol) in DMF (9 ml) was heated to 100 C. for about 6 h. Removal of the solvent under reduced pressure provided (E)-1-(4-bromophenyl)-3-(dimethylamino)-2-(pyridin-4-yl)prop-2-en-1-one (640 mg, 1.546 mmol, 85% yield) as a red oil which was used in the next step without further purification. LC-MS (Method B): m/z 331 (M+H), RT: 1.37 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,100397-96-4, its application will become more common.

Reference:
Patent; GENESTE, Herve; TURNER, Sean Colm; OCHSE, Michael; DRESCHER, Karla; BLACK, Lawrence A.; JANTOS, Katja; US2014/148461; (2014); 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.628691-93-0, name is 2-Chloro-3-fluoroisonicotinic acid, molecular formula is C6H3ClFNO2, molecular weight is 175.55, as common compound, the synthetic route is as follows.Product Details of 628691-93-0

Step i: tert-butyl N-(2-chloro-3-fluoro-4-pyridyl)carbamate Diphenylphosphoryl azide (DPPA) (129 mmol) was added to a mixture of 2-chloro-3-fluoro-pyridine-4-carboxylic acid (85.7 mmol), Et3N (257 mmol) in 1:1 tert-BuOH/toluene (200 mL). The mixture was heated at 110 C. for 4 h. Mixture was diluted with H2O and extracted with DCM. The organic layer was dried (Na2SO4) and concentrated. The residue was purified by flash column chromatography (SiO2, 100:0 to 80:20 DCM/EtOAc) to yield the desired product tert-butyl N-(2-chloro-3-fluoro-4-pyridyl)carbamate.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,628691-93-0, 2-Chloro-3-fluoroisonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; MENET, Christel Jeanne Marie; MAMMOLITI, Oscar; BLANC, Javier; ORSULIC, Mislav; ROSCIC, Maja; US2015/203455; (2015); 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.696-42-4, name is 5-Fluoronicotinonitrile, molecular formula is C6H3FN2, molecular weight is 122.0998, as common compound, the synthetic route is as follows.Application In Synthesis of 5-Fluoronicotinonitrile

INTERMEDIATE 17 5-(3-Iodo-lH-pyrazol-l-yl)nicotinonitrile To 3-iodo-l/J-pyrazole (500 mg, 2.58 mmol) in DMSO (2.6 mL) at 0 C, was added sodium hydride (60% in mineral oil, 113 mg, 2.84 mmol). The reaction was warmed to 25 C and stirred for 60 min before 5-fluoronicotinonitrile (315 mg, 2.58 mmol) was added. The reaction mixture was stirred at 85 C for 5 h before quenched by the addition of water. The reaction mixture was extracted with EtOAc. The combined organic extracts were dried over MgS04 and concentrated in vacuo. The crude mixture was purified by flash chromatography (ISCO Combiflash, 0-50% EtOAc in hexanes) to afford 5-(3-iodo-lH-pyrazol-l-yl)nicotinonitrile, as a white solid. LCMS calc. = 296.96; found = 296.88 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,696-42-4, 5-Fluoronicotinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MOCHIDA PHARMACEUTICAL CO., LTD.; SMITH, Cameron, James; TAN, John, Qiang; ZHANG, Ting; BALKOVEC, James; GREENLEE, William, John; GUO, Liangqin; XU, Jiayi; CHEN, Yi-heng; CHEN, Yili; CHACKALAMANNIL, Samuel; HIRABAYASHI, Tomokazu; NAGASUE, Hiroshi; OGAWA, Kouki; WO2014/120346; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 880870-13-3, 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 880870-13-3 as follows.

Step 1: Preparation of l-(4-(6-chloro-4-methoxypyridin-3-yl)-2-fluorophenyl)pyrrolidin-2- one. [0802] A mixture of 5-bromo-2-chloro-4-methoxypyridine (219 mg, 0.983 mmol), l-(2- fluoro-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)pyrrolidin-2-one (300 mg, 0.983 mmol), Pd(dppf)Cl2 (72 mg, 0.098 mmol) and Na2C03 (313 mg, 2.95 mmol) in dioxane (4 mL) and water (1 mL) was degassed and purged with N2 for 3 times. And the resulting reaction mixture was stirred at 90 C for 4 hours under N2 atmosphere. A black suspension was formed. LCMS showed the purity of the desired product is 63% (Rt = 0.823 min; MS Calcd: 320.1; MS Found: 320.9 [M+H]+). The reaction mixture was diluted with water (10 mL). The aqueous layer was extracted with EtOAc (30 mL x3). The combined organic layer was washed with water (20 mL x2), brine (40 mL), dried over anhydrous Na2S04, filtered and concentrated under reduced pressure. The residue was purified by Combi Flash (20% to 80% EtOAc in PE) to give 1-(4-(6-chloro-4-methoxypyridin-3-yl)-2-fluorophenyl)pyrrolidin-2-one (230 mg, yield: 78%) as a yellow solid. NMR (400 MHz, CDCb) d 2.20-2.28 (2H, m), 2.60 (2H, t, J= 8.0 Hz), 3.84-3.89 (2H, m), 3.90 (3H, s), 6.92 (1H, s), 7.24-7.33 (2H, m), 7.49 (1H, t, J= 8.0 Hz), 8.19 (1H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,880870-13-3, its application will become more common.

Reference:
Patent; PETRA PHARMA CORPORATION; LINDSTROeM, Johan; PERSSON, Lars Boukharta; VIKLUND, Jenny; KESICKI, Edward A.; HICKEY, Eugene R.; DAHLGREN, Markus K.; GERASYUTO, Aleksey I.; (450 pag.)WO2019/126731; (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. 77837-09-3, name is Methyl 6-oxo-1-phenyl-1,6-dihydropyridine-3-carboxylate. A new synthetic method of this compound is introduced below., HPLC of Formula: C13H11NO3

General procedure: Example 1-3 Synthesis of 6-oxo-1-phenyl-1,6-dihydro-3-pyridinecarboxylic acid [0042] After 750 mg (3.27 mmol) of methyl 6-oxo-1-phenyl-1,6-dihydro-3-pyridinecarboxylate was dissolved in 9 mL of methanol and 3 mL of water, 235 mg (9.81 mmol) of lithium hydroxide was added to the solution. Afterward, the resulting reaction solution was stirred at about 50° C. for about 5 hours. After termination of the reaction was determined by liquid chromatography, the solvent was removed in vacuo, followed by addition of aqueous HCl to titrate a pH of the reaction product to pH 2. After filtration of the resulting solid compound (Actual yield: 470 mg, Percent yield: 67percent), the resulting compound was used without purification. [0043] 1H-NMR (DMSO-d6,200 MHz) delta8.18 (s, 1H), 7.88 (d, 1H), 7.49 (m, 5H), 6.54 (d, 2H)

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, 77837-09-3, Methyl 6-oxo-1-phenyl-1,6-dihydropyridine-3-carboxylate.

Reference:
Patent; SK BIOPHARMACEUTICALS CO., LTD.; Maeng, Cheol Young; Jang, Young Koo; Cha, Su Bong; Shin, Hye Won; Joung, Chan Mi; Cha, Hwa Ryun; Yi, Eun Jung; US2013/317059; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 915006-52-9 ,Some common heterocyclic compound, 915006-52-9, molecular formula is C5H4BrIN2, 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.

15.5 g 6-Bromo-2-iodo-pyridin-3-ylamine, 5.9 ml ethyl acrylate, 2.72 g triphenylphosphine and 28.75 ml triethylamine were dissolved in 90 ml acetonitrile. An argon stream was bubbled through the reaction mixture for 10 minutes then 2.33 g palladium(ll)acetate were added and the reaction mixture stirred at 800C. The reaction mixture was filtered hot troupgh a pad of celite then the solvent was removed in vacuo.The residue was purified by chromatography on silica gel to obtain 10.2 g (E)-3-(3-Amino-6-bromo-pyridin-2-yl)-acrylic acid ethyl ester. C10H11BrN2O2 (271.12), MS(ESI+): 273.0, 271.0 (M+H+), Rf(ethyl acetate : n- heptane = 1 :2) = 0.12.

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. 915006-52-9, 6-Bromo-2-iodopyridin-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SANOFI-AVENTIS; WO2009/149820; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 77199-09-8, 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. 77199-09-8, name is Ethyl 5-bromopicolinate, molecular formula is C8H8BrNO2, 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.

(b) Preparation of ethyl 5-ethoxypyridine-2-carboxylate 3 :To a solution of ethyl 5-bromopyridine-2-carboxylate 2 (1.5 g, 6.5 mmol) in 20 mL of EtOH was added a solution of sodium (0.18 g, 7.8 mmol) in 20 mL of EtOH. The mixture was stirred at reflux for 3 h. After removal of all solvent, the residue was purified by column (2: 1 of hexane/ethyl acetate) to give ethyl 5-ethoxypyridine-2-carboxylate 3 as an oil. Yield: 0.26 g, 20%. .HNMR (CDCI3) delta (ppm): 8.38 (d, 1 H), 8.10 (d, 1 H), 8.23 (d, 1 H), 7.22 (dd, 1 H), 4.45 (m, 2 H), 4.25 (m, 1 H), 1.40 (m, 6 H).

According to the analysis of related databases, 77199-09-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; OSLO UNIVERSITY HOSPITAL HF; HOLSWORTH, Daniel; WAALER, Jo; MACHON, Ondrej; KRAUSS, Stefan; VORONKOV, Andrey Edward; GOLDING, Louise; WO2012/76898; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem