Pyridine-derivatives

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 7477-10-3, name is 6-Chloro-5-nitronicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 7477-10-3

Synthesis (compoundof 6- (4-Ethoxyphenylamino) -5-nitronicotinic acid 22-2)[0000150] To a solution of 6-chloro-5-nitronicotinic acid (22-1) (10 g, 49 mmol, 1.0 equiv) in acetonitrile (150 mL) was added triethylamine (15.1 mL, 109 mmol, 2.2 equiv) and 4- ethoxyaniline (6.7 mL, 52 mmol, 1.05 equiv) . The mixture was heated refluxed for 18 hours and concentrated under reduced pressure. The residue was suspended in water (100 mL) and the pH adjusted to 4 with 6N hydrochloric acid. The aqueous phase was extracted with a 2:1 mixture of ethyl acetate and tetrahydrofuran (4 x 100 mL) . The organic layers were combined, dried over sodium sulfate, and concentrated under reduced pressure to give crude compound 22-2 (14 g, 96% yield) as a black 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, 7477-10-3, 6-Chloro-5-nitronicotinic acid.

Reference:
Patent; SIGA TECHNOLOGIES, INC.; DAI, Dongcheng; BURGESON, James, R.; AMBERG, Sean, M.; HRUBY, Dennis, E.; WO2013/123215; (2013); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1003711-43-0, 2-Bromo-5-hydroxy-3-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: C6H6BrNO, blongs to pyridine-derivatives compound. Formula: C6H6BrNO

To a mixture of 2-bromo-5-hydroxy-3-picoline (2.18 g, 11.59 mmol), TEA (19.39 mL, 139 mmol), and MeOH (30 mL, 740 mmol) in a 250 mL pressure tube was added 4,5- bis(diphenylphosphino)-9,9-dimethylxanthene (335 mg, 0.58 mmol) and palladium (II) acetate (65 mg, 0.29 mmol). The mixture was evacuated-purged with CO gas (balloon) 3- times. The valves were closed and the mixture was heated at 70 C for 24 h. The mixture was filtered through a pad of Celite filter aid. The Celite filter aid was washed with MeOH. The filtrate was concentrated in vacuo and dissolved in DCM (50 mL). The organic solution was washed with saturated NaHCO3 (30 mL). The aqueous layer was saturated with NaCl and extracted with 2% IPA in CHCl3 (3 x 20 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The crude was purified by silica gel chromatography using 1 -5% MeOH in DCM to give the product as an off- white solid (1.65 g, 85%). LCMS (ESI, pos.) 168.0 (M+1 )+. 1H NMR (400 MHz, DMSO-d6) delta 10.57 (br. s., 1 H), 8.02 (d, J=2.54 Hz, 1 H), 7.08 (d, J=2.15 Hz, 1 H), 3.79 (s, 3H), 2.44 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1003711-43-0, 2-Bromo-5-hydroxy-3-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer R.; AMEGADZIE, Albert; BOURBEAU, Matthew P.; BROWN, James A.; CHEN, Jian J.; CHENG, Yuan; FROHN, Michael J.; GUZMAN-PEREZ, Angel; HARRINGTON, Paul E.; LIU, Longbin; LIU, Qingyian; LOW, Jonathan D.; MA, Vu Van; MANNING, James; MINATTI, Ana Elena; NGUYEN, Thomas T.; NISHMURA, Nobuko; NORMAN, Mark H.; PETTUS, Liping H.; PICKRELL, Alexander J.; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert M.; SIEGMUND, Aaron C.; STEC, Markian M.; WHITE, Ryan; XUE, Qiufen; (759 pag.)WO2016/22724; (2016); 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. 16744-81-3, name is 4-Methoxypicolinaldehyde, molecular formula is C7H7NO2, 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. category: pyridine-derivatives

2. (R SS2-[4-(4-METHOXYPYRIDIN-2-YL) BUT-2-YL]-3H-I MIDAZO [4. S-B] PYRID INE; A solution of 7.2 g of tributyl-{1-(3H-imidazo [4,5-b] PYRIDIN-2-YL)-PROPYL}-PHOSPHONIUM chloride (compound A2) in tetrahydrofurane is added to a suspension of 720 mg of sodium hydride (60percent strength suspension in paraffin) in 180 ml of tetrahydrofurane. After 15 min stirring, a solution of 0.500 g of 4-methoxypyridine- 2-carbaldehyde (Ashimori et AL., Chem. Pharm. Bull. 38,2446-2458 (1990) ) in tetrahydrofurane is added dropwise and the reaction mixture is heated at 80°C for 6 h. The mixture is then evaporated to dryness and the resulting residue chomatographed on silica gel using DICHLOROMETHANE/METHANOL 20: 1 to give 3.58 g of a colorless, amorpheous solid, which is dissolved as obtained in 200 ml of methanol. 2.9 ml of trifluoracetic acid and 788 mg of palladium on active carbon (10percent Pd) are added and the suspension is stirred at room temperature for 2.5 d under hydrogen atmosphere. Then the catalyst is filtered off and the reaction mixture is concentrated to dryness. After chromatographical purification of the residue on silica gel (DICHOROMETHANE/METHANOL 10: 1 to 5: 1) and evaporation of the eluents, 1.4 g of the title compound are obtained as an oil. MS: 283.1 (MH+). TLC: Rf = 0.48 (DICHLOROMETHANE/METHANOL 10: 1).

With the rapid development of chemical substances, we look forward to future research findings about 16744-81-3.

Reference:
Patent; ALTANA PHARMA AG; WO2005/30768; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89415-54-3, 5-Bromo-N2-methylpyridine-2,3-diamine, 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, Product Details of 89415-54-3, blongs to pyridine-derivatives compound. Product Details of 89415-54-3

In a flask were combined 2-methylpropanamide (Aldrich, cat144436: 285 mg, 3.28 mmol), THF (2 mL) and triethyloxonium tetrafluoroborate (Aldrich, cat90520: 0.617 g, 3.25 mmol). The reaction mixture was allowed to stir at room temperature for 2 hours. The solvent was removed under reduced pressure and the residue was dissolved in ethanol (1.9 mL). To this residue was added a suspension of 5-bromo-N2-methylpyridine-2,3-diamine (200 mg, 0.99 mmol) [Combi-Blocks cat AN-3965] in ethanol (6.7 mL). The mixture was then stirred at 80 C. for 1 hour. After the crude reaction mixture had cooled to room temperature the solvent was removed under reduced pressure. The residue was purified by flash chromatography on a silica gel column eluting with 0 to 20% MeOH/DCM to give the desired product (48 mg, 19% yield). LC-MS calculated for C10H13BrN3 (M+H)+: m/z=254.0. found 254.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89415-54-3, 5-Bromo-N2-methylpyridine-2,3-diamine, and friends who are interested can also refer to it.

Reference:
Patent; Incyte Corporation; Wu, Liangxing; Konkol, Leah C.; Lajkiewicz, Neil; Lu, Liang; Xu, Meizhong; Yao, Wenqing; Yu, Zhiyong; Zhang, Colin; He, Chunhong; (107 pag.)US2016/9712; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 117846-58-9, 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.117846-58-9, name is 2,6-Dibromo-3,5-dimethylpyridine, molecular formula is C7H7Br2N, molecular weight is 264.95, as common compound, the synthetic route is as follows.

To a solution of 2,6-dibromo-3,5-dimethylpyridine (1.0 g, 3.77 mmol) in toluene (30 mL) was added n-BuLi (1.5 mL, 3.77 mmol) dropwise at -78 C. After 1 h, DMF (358 mg, 4.9 mmol) was added to the mixture for additional lh. The mixture was adjusted to pH = 34 using HC1 and extracted with EtOAc (50 mL x 3) and the organic layers were concentrated and purified by chromatography (silica, ethyl acetate/petroleum ether =1/10) to afford 6-bromo-3,5- dimethylpicolinaldehyde (242 mg, 1.13 mmol, 30%) as a white solid. ESI-MS (EI, m/z): 214.1 [M+H].

Statistics shows that 117846-58-9 is playing an increasingly important role. we look forward to future research findings about 2,6-Dibromo-3,5-dimethylpyridine.

Reference:
Patent; NAVITOR PHARMACEUTICALS, INC.; O’NEILL, David John; SAIAH, Eddine; KANG, Seong Woo Anthony; BREARLEY, Andrew; BENTLEY, Jonathan; (565 pag.)WO2018/89433; (2018); 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.112110-07-3, name is 5-(Trifluoromethyl)pyridin-3-amine, molecular formula is C6H5F3N2, molecular weight is 162.11, as common compound, the synthetic route is as follows.Quality Control of 5-(Trifluoromethyl)pyridin-3-amine

Step 5: 4-Methyl-3-(9H-pyrimido[4, 5-bJindol- 7-yl)-N-[5-(trifluoromethyl)pyridin-3-yl]benzamideTo a vial was added 4-methyl-3-(9H-pyrimido[4,5-b]indol-7-yl)benzoic acid (15.2 mg, 0.0501 mmol), DMF (0.32 mL), and AWN’N’-tetramethyl-O-(7-azabenzotriazol-l-yl)uronium hexafluorophosphate (22.9 mg, 0.0601 mmol). This mixture was stirred 15 min at RT. To the mixture was then added 5-(trifluoromethyl)pyridin-3-amine (10.6 mg, 0.0651 mmol. The resulting mixture was stirred at 70 0C for 18 h. LCMS indicated complete consumption of the activated ester (M+H 422) and showed product (M+H 448). The product was isolated by prep HPLC/MS using a 19 mm x 100 mm C18 column; 28%CH3CN-H2O (0.1% TFA), 1 min, to 48% at 6 min; 30 mL/min. The HPLC fractions containing the product were freeze dried to yield a light yellow solid, 5.6 mg, 20% yield. FMR showed that it was the mono TFA salt; and contained some residual PF6. 1H NMR (DMSOd6) delta 13.29 (s, IH, NH); 10.76 (s, IH, amide NH); 9.72 (s, IH); 9.22 (s, IH); 9.20 (s, IH); 8.69 (s, IH); 8.62 (s, IH); 8.44 (d, IH); 7.98 (m, 2H); 7.66 (s, IH); 7.56 (d, IH); 7.53 (d, IH).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,112110-07-3, 5-(Trifluoromethyl)pyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; INCYTE CORPORATION; WO2008/79965; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 42182-25-2, 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. 42182-25-2, name is 1-(2-Aminopyridin-4-yl)ethanone, molecular formula is C7H8N2O, 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 mixture of (36) (168 mg, 1.234 mmol) in MeOH (10 mL), under nitrogen at 0 C., was added sodium borohydride (46.7 mg, 1.234 mmol). The reaction mixture was stirred at RT for 2 hr, and the volatiles were removed under reduced pressure. The residue was taken up into EtOAc (25 mL), and extracted with saturated aq NaHCO3 solution (30 mL). The aqueous layer was back extracted with EtOAc (2*20 mL), and the combined organic extracts were washed with brine (30 mL), dried and the solvents removed in vacuo to give 1-(2-aminopyridin-4-yl)ethanol (37) (77 mg, 45%) as a yellow oil: m/z 139 (M+H)+ (ES+).

According to the analysis of related databases, 42182-25-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Charron, Catherine Elisabeth; Fenton, Robert; Crowe, Scott; Ito, Kazuhiro; Strong, Peter; Rapeport, William Garth; Ray, Keith; US2012/244120; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 3222-56-8, Adding some certain compound to certain chemical reactions, such as: 3222-56-8, name is 2-Methylnicotinic acid,molecular formula is C7H7NO2, 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 3222-56-8.

To a solution of acid 2-methylpyridin-3-carboxylic (0.40 g, 2.90 mmol, 1 eq) in DMF dry (4.0 mL), ammonium chloride (0.93 g, 17.50 mmol, 6 eq), HOBt (0.57 g, 4.20 mmol, 1.44 eq), EDCI (0.81 g, 4.20 mmol, 1.44 eq) and N-methylmorpholine (0.46 mL, 4.20 mmol, 1.44 eq) were subsequently added. The reaction was stirred at room temperature, under nitrogen for 2.5 h. Evaporation of the solvent gave a residue which was purified by column chromatography (neutral alumine oxide, Brockmann grade III) using EtOAc as eluant to give 9 as white solid after crystallization with EtOAc (0.27 g, 69%). Mp. 163-166 C. 1H NMR (300 MHz, CD3OD) delta 8.45 (dd, J = 4.9/1.8 Hz, 1-H), 7.83 (dd, J = 7.6/1.5 Hz, 1-H), 7.30 (dd, J = 7.6/4.9 Hz, 1-H), 2.61 (s, 3-H); 13C NMR (75 MHz, CD3OD) delta 172.0, 155.4, 149.2, 135.7, 132.2, 121.2, 21.2; GC-MS m/z 136 (M)+; IR (KBr) 2768, 2389, 1926, 1692, 1448, 1365 cm-1. Anal. Calcd for C7H8N2O: C, 61.75; H, 5.92; N, 20.58. Found: C, 61.91; H, 6.20; N, 20.10.

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. 3222-56-8, 2-Methylnicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Galli, Ubaldina; Mesenzani, Ornella; Coppo, Camilla; Sorba, Giovanni; Canonico, Pier Luigi; Tron, Gian Cesare; Genazzani, Armando A.; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 58 – 66,9;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 19235-89-3, 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. 19235-89-3, name is 4-Chloropyridine-2-carbonitrile. A new synthetic method of this compound is introduced below.

A three-neck, 3L round bottomed flask fitted with a mechanical stirrer and a reflux condersor was charged with 4-aminophenol (41.35 g, 0.38 mol) and N5N- dimethylacetamide (500 mL). The resulting solution was degassed with bubbling nitrogen before potassium tert-butoxide was added portionwise (44.54 g, 0.40 mol). The solution became green at first, then became an off-white suspension, to which was added 4- chloropyridine-2-carbonitrile (50.00 g, 0.36 mol) in N,N-dimethylacetamide (300 mL) in one portion. The mixture turned brown within minutes and it was heated to 900C overnight. In the next morning, the mixture was cooled to rt and the solvent was removed under vacuum. The resulting residue was partitioned between water (1.5 L) and EtOAc (1.5 L). K2CO3 was added to adjust the pH to slightly basic and the layers were separated. The aqueous layer was extracted with EtOAc (IL). The combined organic phase was dried over MgSO4, filtered and concentrated. The resulting residue was dissolved in dichloromethane and absorbed onto a plug of silica gel (~ 1 kg). It was then eluted with 25% to 75% EtOAc in hexanes to afford 4-(4-aminophenoxy)pyridine-2-carbonitrile (18.9 g, 25%): 1H NMR (DMSO-^5) delta ppm 8.48 (d, IH), 7.51 (d, IH), 7.04 (dd, IH), 6.83 (dd, 2H), 6.60 (dd, 2H), 5.18 (s, 2H); MS ES 212 (M+H), RT 0.97 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,19235-89-3, 4-Chloropyridine-2-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2006/110763; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 934180-48-0, 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.934180-48-0, name is 4-Chloro-2-methoxy-3-nitropyridine, molecular formula is C6H5ClN2O3, molecular weight is 188.57, as common compound, the synthetic route is as follows.

Tin(ll)chloride dihydrate (12 g, 53.19 mmol) was added to a solution of 4-chloro-2- methoxy-3-nitropyridine (2 g, 10.64 mmol) in ethyl acetate (30 ml.) and the resultant suspension heated at 70 C with stirring for 2 h. The reaction mixture was cooled to ambient temperature, the pH adjusted to pH 9-10 by addition of saturated sodium carbonate (aq.) and extracted with ethyl acetate (3 x 10OmL). The combined extracts were dried (MgSO4) and concentrated in vacuo to give the crude product. Purification by chromatography on silica gel with EtOAc:heptane (1 :9, v/v) as eluent afforded the product as a colourless oil (1.28 g, 76 %).Data for 3-amino-4-chloro-2-methoxypyridine: MS (ESI) m/z: 159/161 ([M+H]+).

The chemical industry reduces the impact on the environment during synthesis 934180-48-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; N.V. ORGANON; WO2007/39563; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem