Month: April 2022

Application of 130473-27-7, 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. 130473-27-7, name is 1H-Pyrrolo[2,3-c]pyridine-5-carboxylic acid. A new synthetic method of this compound is introduced below.

Coupling: Example 24 is obtained as a white solid (40% yield) using acid C176 using Method C with non-critical changes. HRMS (FAB) calculated for C15H18N4O+H: 271.1559, found 271.1562 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,130473-27-7, 1H-Pyrrolo[2,3-c]pyridine-5-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Wishka, Donn G.; Reitz, Steven Charles; Piotrowski, David W.; Groppi JR., Vincent E.; US2003/45540; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1235036-15-3, Adding some certain compound to certain chemical reactions, such as: 1235036-15-3, name is tert-Butyl 3-bromo-6-chloropicolinate,molecular formula is C10H11BrClNO2, 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 1235036-15-3.

To Example 1.1.10 (100 mg) and tert-butyl3-bromo-6-chloropicolinate (52.5 mg) in dioxane(2 mL) was added tris(dibenzylideneacetone)dipalladium(O) (8.2 mg), K3P04 (114 mg), 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphaadamantane (5.24 mg) and water (0.8 mL). The mixturewas stirred at 95 oc for 4 hours, diluted with ethyl acetate and washed with water and brine. Theorganic layer was dried over Na2S04 , filtered, concentrated and purified by flash chromatography,eluting with 20% ethyl acetate in heptanes and then with 5% methanol in dichloromethane, to providethe title compound. MS (ESI) m/e 643.3 (M+Ht

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. 1235036-15-3, tert-Butyl 3-bromo-6-chloropicolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBVIE INC.; BOGHAERT, Erwin, R.; JUDD, Andrew, S.; PHILLIPS, Andrew, C.; SOUERS, Andrew, J.; BRUNCKO, Milan; (503 pag.)WO2017/214301; (2017); 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.39903-01-0, name is 2-Amino-5-bromo-3-pyridinol, molecular formula is C5H5BrN2O, molecular weight is 189.01, as common compound, the synthetic route is as follows.COA of Formula: C5H5BrN2O

Preparation 56-Bromo-oxazolo[4,5-b]pyridine[00122] 2-Amino-5-bromo-3-hydroxypyridine (200 mg, 1.06 mmol) is dissolved in 3 ml of triethylortoformate and a catalytic amount of p-toluenesulfonic acid is added. The mixture is heated to reflux for 5 h, then cooled, diluted with DCM and washed with saturated sodium bicarbonate solution. The organic phase is dried over anhydrous sodium sulfate and evaporated to dryness. The residue is purified by flash column chromatography to afford 212 mg (60%) of the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,39903-01-0, 2-Amino-5-bromo-3-pyridinol, and friends who are interested can also refer to it.

Reference:
Patent; MERZ PHARMA GMBH & CO. KGAA; HENRICH, Markus; WEIL, Tanja; HECHENBERGER, Mirko; MUeLLER, Sibylle; KAUSS, Valerjans; ZEMRIBO, Ronalds; ERDMANE, Elina; SMITS, Gints; WO2011/15343; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 709652-82-4, 2-Amino-5-bromonicotinonitrile, 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, name: 2-Amino-5-bromonicotinonitrile, blongs to pyridine-derivatives compound. name: 2-Amino-5-bromonicotinonitrile

A suspension of 2-amino-5-bromo-3-pyridinecarbonitrile (0.59 g, 3 mmol), DMF-DMA (1 ml, 7.5 mmol), and MeCN (2 ml) was irradiated at 50 C (input power of: 200 W) for2 min. The resulting mixture was cooled to room temperature and poured onto ice cold water. The precipitate was filtered off, washed with water, and dried to afford (1E)-N?-(3-cyano-2-pyridinyl)-N,N-dimethylmethanimidamide (Lacbay et al. 2014). Light yellow solid; yield 95%; m.p. 116-117 C; 1H NMR (400 MHz, DMSO-d6) delta 8.65-8.60 (m, 1H, H-5), 8.46 (d, J = 2.6 Hz, 1H, H-3), 8.32 (d,J = 2.6 Hz, 1H, N=CH), 3.16 (s, 3H, CH3),3.07 (s, 3H,CH3); 13C NMR (100 MHz, DMSO-d6) delta 162.27 (C-2),157.00 (C=N), 153.23 (C-6), 144.32 (C-4), 116.77 (CN), 110.23 (C-5), 102.68 (C-3), 35.00 (C-N); IR (film): 3457(C-N), 3061, 2916, 2795, 2483, 2306, 2214 (CN), 1960, 1625 (C=N), 1562, 1395 cm-1; HRMS (ESI) m/z: calculatedfor C9H10BrN4+ [M + H]+: 253.0089; found: 253.0084.

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

Reference:
Article; Sun, Ya-Quan; Zong, Chao-Yang; Ji, Jin-Yu; Han, Qing; Chemical Papers; vol. 72; 12; (2018); p. 2965 – 2972;,
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. 107867-51-6, name is 5-(Trifluoromethyl)pyridine-2,3-diamine, molecular formula is C6H6F3N3, 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: C6H6F3N3

To a stirred solution of l-(4-(3-cyanobenzamido)phenyl)cyclobutanecarboxylic acid (65 mg, 0.20 mmol) in pyridine (2 mL) was added EDC (97 mg, 0.51 mmol) and 5- (trifluoromethyl)pyridine-2,3-diamine (30 mg, 0.17 mmol) at RT. After the addition was finished, the mixture was stirred at 40 C for 16 h. The reaction was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2S04i filtered and concentrated in vacuo to afford a residue, which was purified by reversed phase HPLC, eluting with water (0.1%TFA)-ACN to give te title compound. MS (EI) m/z 480 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 107867-51-6.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ZHOU, Hua; ACHAB, Abdelghani; FRADERA, Xavier; HAN, Yongxin; LI, Derun; MCGOWAN, Meredeth, A.; SCIAMMETTA, Nunzio; SLOMAN, David, L.; YU, Wensheng; (98 pag.)WO2019/27855; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 142896-15-9, 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 142896-15-9, name is Methyl 2,6-dimethylisonicotinate. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 1.372 g (8.3 mmol) of (3), 60 mg of AlBN and 2.866 g (16.1 mmol) of NBS in 120 ml of CCl4 is refluxed under a nitrogen atmosphere and under irradiation with a 100 W lamp, for 8 hours. The reaction medium is then returned to room temperature, after which it is washed with 200 ml of saturated NaHCO3 solution. After removing the lower phase (CCl4), the aqueous phase is extracted 4 times with 50 ml of CHCl3; the combined organic extracts are then washed with 100 ml of H2O, dried (Na2SO4) and then concentrated to dryness. Purification of the residue obtained by chromatography on silica [gradient: cyclohexane-CH2Cl2 (80/20) to pure CH2Cl2) makes it possible to separate out a first fraction of the bromo derivative (4), from the polybromo species, from a mixture of isomers of symmetrical and asymmetrical dibromo derivatives and from the monobromo species also formed. [0153] In order to have available a larger amount of methyl 2,6-dibromomethyl isonicotinate, the monobromo compound isolated above [0.543 g (2.2 mmol)] is mixed with 0.4 g (2.2 mmol) of NBS, 23 mg of AIBN and 50 ml of CCl4 and is then treated under the above bromination conditions to give a second fraction of (4). [0154] Finally, a purification by chromatography on silica [gradient: pure cyclohexane to cyclohexane/EtOAc (85/15)] of the mixtures of dibromoisomers, isolated in the above two reactions, gives a final fraction of (4), i.e. 596 mg in total (22%). [0155] m.p.: 90-92 C. [0156] TLC: Rf: 0.6 (SiO2/CH2Cl2) [0157] HPLC: Tr: 20 min 5 sec [0158] UV: CHCl3: 290.8 nm (4270); 240.3 nm (3010) [0159] NMR: 1H CDCl3; internal reference TMS [0160] 3.98 (s, 3H, CH3); 4.58 (s, 4H, CH2); 7.92 (s, 2H, Py) [0161] 13C CDCl3; internal reference 77.0 ppm [0162] 32.8 (CH2); 52.9 (OCH3); 122.2 (Ct); 139.8, 157.9 (Cq); [0163] 164.7 (CO). [0164] MS (EI): 322.9 (M+, 15); 243.9 (M+-Br, 100); 163 (M+-2Br, 15.7). [0165] MA: C9H9NO2Br2 (322.98) [0166] Calculated: C 33.47H 2.80 N 4.33 O 9.90 [0167] Found: C 33.69H 2.81 N 4.29 O 10.17

According to the analysis of related databases, 142896-15-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Autiero, Herve; Bazin, Herve; Mathis, Gerard; US2004/92726; (2004); 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. 55404-31-4, name is 3-Bromo-2-chloro-4-methylpyridine. A new synthetic method of this compound is introduced below., Product Details of 55404-31-4

Step 3: In a sealed tube, NaOMe (25% in MeOH, 3.1 mL, 13 mmol) was added to a solution of compound 94 (1.8 g, 8.7 mmol) in MeOH (17 mL). The reaction was heated at 75 C for 3 days. The reaction mixture was cooled to room temperature, diluted with EtOAc, washed with saturated NH4CI and brine, dried over MgS04, filtered and concentrated. The crude product was purified by flash chromatography over silica gel, which was eluted with heptanes/EtOAc (0-15%) to afford compound 95 as a clear oil (991 mg, 56% yield). 1H NMR (400 MHz, DMSO-c/6) delta 8.00 (d, J = 5.0 Hz, 1 H), 6.98 (d, J = 4.8 Hz, 1 H), 3.90 (s, 3 H), 2.35 (s, 3 H).

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, 55404-31-4, 3-Bromo-2-chloro-4-methylpyridine.

Reference:
Patent; PFIZER INC.; BAILEY, Simon; BURKE, Benjamin, Joseph; COLLINS, Michael, Raymond; CUI, Jingrong, Jean; DEAL, Judith, Gail; HOFFMAN, Robert, Louis; HUANG, Qinhua; JOHNSON, Ted, William; KANIA, Robert, Steven; KATH, John, Charles; LE, Phuong, Thi, Quy; MCTIGUE, Michele, Ann; PALMER, Cynthia, Louise; RICHARDSON, Paul, Francis; SACH, Neal, William; WO2013/132376; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 13472-56-5, 2-Methoxy-5-methylpyridine, 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, Formula: C7H9NO, blongs to pyridine-derivatives compound. Formula: C7H9NO

n-BuLi (2.5 M, 1.95 mL) was added dropwise to a solution of 2-methoxy-5-methylpyridine (500 mg, 4.06 mmol) in THF (9 mL) at -78C and the mixture was stirred at -40C for 0.5 hours. A solution of triisopropyl borate (1.15 g, 6.09 mmol) in THF (1 mL) was added dropwise, and stirring continued for 0.5 hours at -78C.Then the reaction mixturre was stirred at 20C for an additional 12 hours. The reaction mixture was poured into water (10 mL) and stirred for 5 minutes.The aqueous phase was extracted with dichloromethane. The organic phase was washed with brine, dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (petroleum ether/ethyl acetate) to afford the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13472-56-5, 2-Methoxy-5-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; MARIGO, Mauro; (142 pag.)WO2019/121840; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 945954-94-9, 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.945954-94-9, name is Methyl 6-bromo-3-methoxypicolinate, molecular formula is C8H8BrNO3, molecular weight is 246.06, as common compound, the synthetic route is as follows.

44 mmol of sodium borohydride are added in portions to a solution of 2.2 mmol of methyl 6- bromo-3-methoxypyridine-2-carboxylate in 750 ml of methanol. The mixture is stirred at room temperature for 2 days. Water is added to the reaction mixture, and it is extracted with dichloromethane (3x). The combined organic phases are dried with sodium sulphate and concentrated. The solid resulting after addition of n-hexane is filtered off with suction and dried.

The chemical industry reduces the impact on the environment during synthesis 945954-94-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SPEEDEL EXPERIMENTA AG; WO2007/31558; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 880870-13-3, Adding some certain compound to certain chemical reactions, such as: 880870-13-3, name is 5-Bromo-2-chloro-4-methoxypyridine,molecular formula is C6H5BrClNO, 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 880870-13-3.

The compound (2.82 g, 12.68 mmol) obtained in Step 8 was dissolved in tetrahydrofuran (10 ml) and, under an argon atmosphere, dichlorobis(triphenylphosphine) palladium(II) (445 mg, 0.63 mmol) and 1 M 3-chloro-2-fluorobenzylzinc bromide tetrahydrofuran solution (17.75 ml, 17.75 mmol) were added dropwise, and the mixture was heated under reflux at 80 C. for 2 hr. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous ammonium chloride solution and saturated brine, and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography (hexane:ethyl acetate=5:1) to give the object product as a white solid (2.19 g, yield 60%). 1H NMR(CDCl3 300 MHz) (delta) ppm: 3.86 (3H, s), 3.91 (2H, s), 6.79 (1H, s), 6.94-7.01 (2H, m), 7.23-7.28 (1H, m), 8.03 (1H, s)

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. 880870-13-3, 5-Bromo-2-chloro-4-methoxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Satoh, Motohide; Aramaki, Hisateru; Nakamura, Hiroshi; Inoue, Masafumi; Kawakami, Hiroshi; Shinkai, Hisashi; Matsuzaki, Yuji; Yamataka, Kazunobu; US2006/84665; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem