Month: April 2022

Reference of 121643-44-5, 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.121643-44-5, name is 2-Methoxy-3-(trifluoromethyl)pyridine, molecular formula is C7H6F3NO, molecular weight is 177.1239, as common compound, the synthetic route is as follows.

Intermediate 1 : 5-Bromo-2-methoxy-3-trifluoromethyl-pyridineTo 2-methoxy-3-(trifluoromethyl)pyridine (20.0 g, 1 13.0 mmol) and 1 ,3-dibromo-5,5- dimethylimidazolidine-2,4-dione (43.6 g, 152.0 mmol) was added TFA (80 mL) and the resulting mixture stirred at rt for 18h under argon. The TFA was removed in vacuo (50 mbar, 45C) and the residue suspended in tert-butyl methyl ether (200 mL). The resulting colourless solid was removed by filtration and washed with tert-butyl methyl ether (50 mL). The filtrate was concentrated in vacuo and suspended in EtOAc (50 mL) The insoluble colourless solid was removed by filtration and washed with EtOAc (50 mL).The filtrate was concentrated in vacuo, diluted with heptane/ tert-butyl methyl ether (5/1 , 20 mL) and the insoluble colourless solid was removed by filtration. The filtrate was purified by column chromatography on silica gel with heptane / EtOAc, 100/0 to 90/10. The crude product was filtered through a plug of NaHC03 (20g) and the filtrate evaporated in vacuo to give a golden oil (27.9 g). The oil was dissolved in heptanes (20 mL) and purified by filtered through a plug of silica gel (80 g), eluting with heptane to give 5-bromo-2-methoxy-3-(trifluoromethyl)pyridine as a colourless oil (22.5g, 74% yield). 1H-NMR (400 MHz, DMSO-d6, 298 K): delta ppm 4.03 (s, 3H) 7.95 (d, 1 H) 8.4 (d, 1 H).

The chemical industry reduces the impact on the environment during synthesis 121643-44-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS AG; FERNANDES GOMES DOS SANTOS, Paulo Antonio; HOeGENAUER, Klemens; HOLLINGWORTH, Gregory; SOLDERMANN, Nicolas; STOWASSER, Frank; TUFILLI, Nicola; ZECRI, Frederic; WO2013/1445; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 92992-85-3, 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 92992-85-3, name is 2-Bromo-3,5-dimethylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2-bromo-3,5-dimethylpyridine D14 (0.050 g) in dry Toluene (1 ml) were added sodium terbutoxide (0.036 g, 0.376 mmol), Pd2(dba)3 (0.024 g, 0.027 mmol) , BINAP (0.050 g, 0.081 mmol) and benzophenone immine (0.054 ml, 0.322 mmol). The resulting mixture was degassed (3 x pump/N2) then heated to 80 0C. After 1.5 hours the mixture was cooled to room temperature, diluted with Et2O (100 ml) and filtered through a celite pad. The solvents were evaporated. The resulting oil was dissolved with THF (20 ml) and HCl 2 M in water (0.269 ml, 0.537 mmol) was added and stirred at room temperature for 3 hours. The solution was concentrated in vacuo and the mixture was neutralized with saturatedNaHCO3 aqueous solution and DCM was added, the two layers were separated, the aqueous layer was extracted with DCM (3 x 100 ml). The collected organic layers were filtered through a phase separator and evaporated. The red oil obtained was purified by flash chromatography on silica gel (Flash Master personal, 1O g cartridge eluting first with Cy 80%: EtOAc 20%, and then with NH32 M in MeOH). The fractions were collected, the solvent was removed in vacuo obtaining the title compound D15 (0.022 g). MS: (ES/+) m/z: 123 (M+l). C7H10N2 requires 122. 1H NMR (400 MHz, CDCl3) delta ppm: 7.77 (s, 1 H), 7.15 (s, 1 H), 4.5-4.30 (br.s, 2 H), 2.19 (s, 3 H), 2.13 (s, 3 H).

According to the analysis of related databases, 92992-85-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; ALVARO, Giuseppe; AMANTINI, David; WO2010/72722; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 75279-39-9, 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 75279-39-9, name is N-(4-Aminopyridin-2-yl)acetamide. This compound has unique chemical properties. The synthetic route is as follows.

Immediately add 45% HBF4 water to solid compound d obtained by rotary evaporation of the above solutionSolution (600mL, 10.8mo1),After stirring, the solid was completely dissolved and ethanol (200 mL) was added.Ice salt bath cooled to below -5C,Isoamyl nitrite (150 mL, 1.12 mol) was added dropwise.Control temperature does not exceed 0 C,And stir the reaction below 0C for 3h.After the reaction was completed, tetrahydrofuran (200 mL) was added.Cool to below 0C,Suction filtrationThe solid was washed twice with tetrahydrofuran (20 mL) and dried in a vacuum desiccator to obtain a solid compound e (213.25 g, 85.3%) with a purity of 96%.The diazonium fluoborate (250g, 1mo1) was put into a dry 1L triple reaction flask.Heat to 120C,Solid decomposition,White smoke emerged from the reaction flask.Continue heating to exhaust white smoke.Solid decomposition is complete.Prepare a 40% NaOH solution (300 mL)The solids on the condenser tube are washed into the reaction flask.Heat reflux,As the product is sublimated,The continuous condensation of solids on the condenserCollect the solids,Repeat the above operation,2-amino-4-fluoropyridine (70 g, 62.5%) was obtained,98% purity.

According to the analysis of related databases, 75279-39-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Lingkai Pharmaceutical Technology Co., Ltd.; Lu Qian; (7 pag.)CN107759515; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 97944-43-9, 3-Bromo-5-methylpyridin-4-amine, 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, Application In Synthesis of 3-Bromo-5-methylpyridin-4-amine, blongs to pyridine-derivatives compound. Application In Synthesis of 3-Bromo-5-methylpyridin-4-amine

step 2 A suspension of 98 and toluene (100 mL) was heated to 110 C until the solid dissolved. The the warm solution was added TEA (30 mL, 0.216 mmol) and acetic anhydride (20.4 mL, 22. 1g, 0.216 mmol) and the reaction was heated for 3 h. An additional 30 mL of AC2O was added after 3 h and an additional 30 mL of TEA was added after 6 h. The solution was concentrated in vacuo and the residue dissolved in EtOAc (500 mL) and was twice with H20 (200 mL). The aqueous extracts were reextracted twice with EtOAc (200 mL) and the combined EtOAc extracts were dried (MGS04), filtered and evaporated to afford a brown oil. The crude product was purified by flash chromatography over Si02 (0 to 20% EtOAc/hexane) to afford impure yellow oil which was subjected to a second flash chromatography over SI02 (20 to 50% EtOAc/hexane) to afford 99 (12.1 g).

The synthetic route of 97944-43-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2005/16892; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1221171-70-5, 2-Chloro-6-(trifluoromethoxy)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, SDS of cas: 1221171-70-5, blongs to pyridine-derivatives compound. SDS of cas: 1221171-70-5

5-amino-2-chloro-6-trifluoromethoxypyridine (39); At 0 0C, diisopropylamine (1.7 g, 2.4 mL, 16.7 mmol, 1.1 eq) was added dropwise to a solution of butyllithium (1.56 M in hexane, 10.7 mL, 16.7 mmol, 1.1 eq) in THF (25 mL). At -78 0C, a solution of 2-chloro-6-trifluoromethoxypyridine (2, 3.0 g, 15.2 mmol,1 eq) in THF (7 mL) was added dropwise followed after 2 h by benzenesulfonyl azide(3.3 g, 18.2 mmol, 1.2 eq). The reaction mixture was allowed to reach 25 0C before being treated with a saturated aqueous solution of ammonium chloride (30 mL) and extracted with diethylehter (3 x 20 mL). The combined organic layers were dried over sodium sulfate and evaporated to afford a crude red oil of 5-azido-2-chloro-6- trifluoromethoxy pyridine. It was then dissolved in anhydrous diethylether (100 mL) and added dropwise to a suspension of lithium aluminium hydride (690 mg, 18.2 mmol, 1.2 eq) in diehtylether (100 mL). The reaction mixture was heated under reflux for 5 h before being treated with water (100 mL) and extracted with diethylether (3 * 80 mL). The combined organic layers were dried over sodium sulfate before being evaporated. The crude product was purified by chromatography on silica gel using ethyl acetate/cyclohexane (3:7) as eluent which afforded pure 5-amino-2-chloro-6- trifluoromethoxy pyridine (39, 2.3 g, 10.8 mmol, 71%) as yellow crystals; m.p. 42-45 0C.1H NMR (CDCl3, 300 MHz): delta = 6.98 (d, J = 8.2 Hz, 1 H), 6.95 (d, J = 8.2 Hz, 1 H), 3.83 (bs, 2 H). – 19F NMR (CDCl3, 282 MHz): delta = -56.5 – 13C NMR (CDCl3, 75 MHz): delta = 142.5, 135.3, 131.1, 126.3, 122.7, 120.1 (q, J = 262 Hz). – C6H4ClF3N2O (212): calcd. (%) C 33.90, H 1.90, N 13.18; found C 33.54, H 2.06, N 13.00.

The synthetic route of 1221171-70-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER CROPSCIENCE AG; PAZENOK, Sergii; VORS, Jean-Pierre; LEROUX, Frederic, R.; MANTEAU, Baptiste; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITE DE STRASBOURG; WO2010/40461; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 197376-47-9, 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. 197376-47-9, name is Ethyl 6-Chloropyridine-3-acetate. A new synthetic method of this compound is introduced below.

(6-Chloro-pyridin-3-yl)-acetic acid ethyl ester (30 mg, 0.149 mmol), tetrakis(triphenylphosphine)palladium (0) (16 mg, 0.014 mmol) and potassium phosphate (32 mg, 0.149 mmol) were added to a solution of (E)-1-(4-{1-[3,5-dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1-ethyl-propyl}-2-methyl-phenyl)-3-ethyl-1-penten-3-ol (Example 38-(6); 50 mg, 0.099 mmol) in N,N-dimethylformamide (0.5 mL). After replacement with nitrogen, the mixture was stirred with microwave heating at 140C for 10 minutes. Then, ethyl acetate was added to the reaction mixture, which was washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate = 4:1) to give the target compound as a colorless oil (11.6 mg, 22%). 1H-NMR (chloroform-d): 0.65 (6H, t, J=7.25Hz), 0.93 (6H, t, J=7.25Hz), 1.29 (3H, t, J=7.26Hz), 1.65 (4H, q, J=7.26Hz), 1.99 (6H, s), 2.09 (4H, q, J=7.26Hz), 2.33 (3H, s), 3.67 (2H, s), 4.21 (2H, q, J=7.25Hz), 6.02 (1H, d, J=15.99Hz), 6.75 (1H, d, J=15.82Hz), 6.89 (2H, s), 6.98-7.01 (2H, m), 7.22 (1H, d, J=8.08Hz), 7.31 (1H, d, J=8.90Hz), 7.71 (1H, dd, J=8.08, 2.31Hz), 8.59 (1H, d, J=1.82Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,197376-47-9, Ethyl 6-Chloropyridine-3-acetate, and friends who are interested can also refer to it.

Reference:
Patent; CHUGAI SEIYAKU KABUSHIKI KAISHA; EP1894911; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 64951-08-2, 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. 64951-08-2, name is Imidazo[1,2-a]pyridine-2-carboxylic acid, molecular formula is C8H6N2O2, 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 imidazo[l ,2- a]pyridine-2-carboxylic acid (5.89 g, 36.60 mmol) in dichloromethane (350 mL) was added bis(2-oxo-3-oxazolidinyl)phosphinic chloride (BOP-Cl) (9.3 g, 36.6 mmol) and the mixture was stirred at room temperature for 4 hours. Triethylamine (15.0 mL) and 4-(4-(2-(tert-butyl)-6- (trifluoromethyl)pyrimidin-4-yl)piperazin-l-yl)butan-l -amine (13.14 g , 36.6 mmol) were added and the mixture was stirred at room temperature overnight . The reaction mixture was concentrated under reduced pressure and the residue was partitioned between EtOAc and water. The organic layers were dried over anhydrous sodium sulfate, filtered and the filtrate was evaporated under reduced pressure. The residue obtained was purified by column chromatography over silica using EtOAc-MeOH (10: 1) as the eluent to yield 6.0 g (32%) of the desired product. A solution of the free base in ether was treated with 1.0 molar solution of HCl in diethyl ether to obtain the dihydrochloride salt, mp 253-255 C. TLC Rf 0.29 (CHCl3-MeOH, 90: 10); 1H NMR (DMSO-d6) delta 1.31 (s, 9H), 1.62-1.69 (m, 2H), 1.80-1.88 (m, 2H), 2.88-3.19 (broad hump, 1H), 3.10-3.17 (m, 2H), 3.37-3.33 (q, 2H), 3.52-3.60 (m, 4H), 4.32-4.86 (b, 2H), 7.1 1 (s, 1H), 7.13-7.18 (m, 1H), 7.50-7.57 (t, 1H), 7.65 (dd, J = 9.2, 9.0 Hz, 1H), 8.53 (s, 1H), 8.57 (bs, 1H), 8.68 (d, J= 6.9 Hz, 1H), 1 1.0-1 1.8 (b, 1H). ESI MS m/z 504 (MH)+. Anal. (C25H32F3N7O-2HCl-0.25H2O) Calcd: C, 51.68; H, 5.98; N, 16.87.C1, 12.20. Found: C, 51.64; H, 6.00; N, 16.89, CI, 1 1.97

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 64951-08-2, Imidazo[1,2-a]pyridine-2-carboxylic acid.

Reference:
Patent; SOUTHERN RESEARCH INSTITUTE; ANANTHAN, Subramaniam; WO2014/59265; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 63237-88-7, Pyrazolo[1,5-a]pyridine-2-carboxylic acid, 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, 63237-88-7, blongs to pyridine-derivatives compound. Product Details of 63237-88-7

Preparation 98Methyl 6-({Gamma(1 R)-1 -(4-fluorophenyl)propyll(pyrazolori ,5-alpyridin-2- ylcarbonyl)amino}methyl)pyridine-2-carboxylateTo a stirred solution of amine from Preparation 17 (42mg, 0.14mmol) in dichloromethane (1 ml_) was added pyrazolo[1 ,5-a]pyridine-2-carboxylic acid (22.5mg, 0.14mmol) followed by triethylamine (39muIota_, 0.278mmol) and N-(3- dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (26.6mg, 0.14mmol). The reaction was stirred at room temperature for 40 hrs after this time TLC showed only a small amount of conversion. 0-(Benzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (52.7mg, 0.14mmol) was added along with triethylamine (39muIota_, 0.278mmol). The reaction mixture was stirred over the weekend. The reaction was then washed with aqueous citric acid, followed by saturated aqueous NaHC03, dried (MgS04) and concentrated in vacuo. The residue was purified by column chromatography (silica, 50% ethyl acetate in pentane as eluent) to give the title compound (10mg, 16%). 1 H NMR (400 MHz, CDCI3): the compound appears to exist as two non-interconverting rotameric forms in CDCI3 in the ratio ca. 2:1. Data for these rotamers are listed separately.Major: delta ppm: 1 .96-2.07 (m, 2H) 3.99 (s, 3H) 4.68 (d, 1 H) 4.92 (d, 2H) 6.07 (t, 1 H) 6.78-6.85 (m, 3H) 6.98 (s, 1 H) 7.12-7.21 (m, 2H) 7.29-7.37 (m, 1 H) 7.40-7.52 (m, 2H) 7.56-7.62 (m, 1 H) 7.86 (d, 1 H) 8.50 (d, 1 H)Minor: delta ppm: 2.08-2.19 (m, 2H) 3.99 (s, 3H) 5.00 (d, 1 H) 5.43 (d, 2H) 6.00 (t, 1 H) 6.71 (t, 1 H) 6.78-6.85 (m, 3H) 7.08 (t, 1 H) 7.29-7.37 (m, 1 H) 7.40-7.52 (m, 2H) 7.56- 7.62 (m, 1 1-1) 7.80 (d, 1 H) 8.16 (d, 1 H).LRMS (ESI) m/z 469 [M+Na]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,63237-88-7, its application will become more common.

Reference:
Patent; PFIZER LIMITED; GLOSSOP, Paul Alan; PALMER, Michael John; ANDREWS, Mark David; WO2012/120398; (2012); 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. 188425-85-6, name is 2-Chloro-N-(4′-chloro-[1,1′-biphenyl]-2-yl)nicotinamide, molecular formula is C18H12Cl2N2O, 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. name: 2-Chloro-N-(4′-chloro-[1,1′-biphenyl]-2-yl)nicotinamide

For a 1 :1 co-crystal of boscalid and 4-hydroxy benzoic acid, 200,0 mg of boscalid, 80,4 mg of 4-hydroxi benzoic acid and 150 muIota of ethanol was grinded in a ball mill (Retsch Modell MM301 ) for 10 minutesby using 20 Hz. The crystalline product gave the PXRD in Figure 4 (table 6).

With the rapid development of chemical substances, we look forward to future research findings about 188425-85-6.

Reference:
Patent; BASF SE; SAXELL, Heidi, Emilia; ISRAELS, Rafel; SCHAeFER, Ansgar; BRATZ, Matthias; HOeFFKEN, Hans, Wolfgang; BRODE, Ingo; NAUHA, Elisa; NISSINEN, Maija; WO2011/54741; (2011); A2;,
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. 905563-79-3, name is 2-Chloro-4-methoxynicotinaldehyde. A new synthetic method of this compound is introduced below., Quality Control of 2-Chloro-4-methoxynicotinaldehyde

(2) Synthesis of 2-chloro-4-methoxy-3-(2-methoxyvinyl)pyridine Under nitrogen atmosphere, 4.07g of (methoxymethyl) triphenylphosphonium chloride was suspended in 50ml of tetrahydrofuran, 1.37g of potassium tert-butoxide was added in an ice-cooling, which was stirred for 10 minutes. 1.02g of 2-chloro-4-methoxypyridine-3-carbaldehyde was dissolved in 20ml of tetrahydrofuran, which was added to reaction liquid, and was stirred for another 40 minutes. Water and diethyl ether were added to reaction liquid, and the organic layer was separated. The resulting organic layer was washed with brine and then dried over anhydrous sodium sulfate. The reaction liquid was concentrated under a reduced pressure after removal of drying agent by filtration. The residue was purified by NH silica gel column chromatography (hexane-ethyl acetate) to give 1.18g of the title compound as a mixture of the geometric isomers.

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, 905563-79-3, 2-Chloro-4-methoxynicotinaldehyde.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP1847535; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem