Month: March 2022

Application of 866775-18-0 , The common heterocyclic compound, 866775-18-0, name is Methyl 3-amino-6-bromo-5-(trifluoromethyl)picolinate, molecular formula is C8H6BrF3N2O2, 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.

3-Amino-6-bromo-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester (Intermediate 3D) (100 mg, 0.334 mmol) was dissolved in 5M HCI (2.5 ml) and heated at 150C, 5.5 bar in the microwave for 1 hour. The reaction mixture was purified by reverse phase chromatography eluting with water/MeCN to afford the title compound. MS m/z 241 [M+H]+. 1H NMR (400 MHz, DMSO – d6) delta 13.33 (1 H, br hump), 7.79 (1 H, s), 7.19 (2H, br s

The synthetic route of 866775-18-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; BALA, Kamlesh, Jagdis; BUDD, Emma; EDWARDS, Lee; HOWSHAM, Catherine; LEGRAND, Darren, Mark; TAYLOR, Roger, John; WO2013/38390; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 909717-95-9, Ethyl 4-methoxypyrazolo[1,5-a]pyridine-3-carboxylate, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

Example 47 4-hydroxypyrazolo[1,5-a]pyridine The compound of Example 23 (4.30 g) was dissolved in dichloromethane (50 mL) in an argon atmosphere. While the solution was kept at 0 C., boron tribromide (1.0 mol/L dichloromethane solution, 23.4 mL) was added and the mixture was stirred for 1 hour. Additional boron tribromide (23.4 mL) was then added and the mixture was stirred at room temperature for another 3 hours. Subsequently, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure to give a yellow powder (4.80 g). To this product, 47% hydrobromic acid (100 mL) was added and the mixture was stirred for 5 hours under reflux. Subsequently, the mixture was made basic by adding sodium hydroxide and then made acidic again by adding hydrochloric acid. The mixture was extracted three times with ethyl acetate and the organic layer was washed with saturated brine and dried over sodium sulfate. Evaporating the solvent under reduced pressure afforded the title compound as a yellow powder (2.10 g) (Process C). 1H-NMR (CDCl3, 400 MHz) delta 5.76 (1H, brs), 6.47 (1H, d, J=7.3 Hz), 6.62-6.65 (2H, m), 7.92 (1H, d, J=2.4 Hz), 8.17 (1H, d, J=6.7 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,909717-95-9, Ethyl 4-methoxypyrazolo[1,5-a]pyridine-3-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Kohno, Yasushi; Adams, David Roger; Ando, Naoki; US2008/207902; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 121643-44-5 , The common heterocyclic compound, 121643-44-5, name is 2-Methoxy-3-(trifluoromethyl)pyridine, molecular formula is C7H6F3NO, 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.

Intermediate 1 : 5-Bromo-2-methoxy-3-trifluoromethyl-pyridine To 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). 1 H-NMR (400 MHz, DMSO-d6, 298 K): delta ppm 4.03 (s, 3H) 7.95 (d, 1 H) 8.4 (d, 1 H).

The synthetic route of 121643-44-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; COOKE, Nigel Graham; FERNANDES GOMES DOS SANTOS, Paulo; GRAVELEAU, Nadege; HEBACH, Christina; HOeGENAUER, Klemens; HOLLINGWORTH, Gregory; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; STOWASSER, Frank; STRANG, Ross; TUFILLI, Nicola; VON MATT, Anette; WOLF, Romain; ZECRI, Frederic; WO2012/4299; (2012); 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. 868551-30-8, name is Methyl 4-methyl-5-nitropicolinate. A new synthetic method of this compound is introduced below., Recommanded Product: 868551-30-8

Example 75A: 2~(4~Methyl~5~nitro^yridin-2-yl)~chromen-4-one O-tert- butyl-oximeA solution of 2′-hydroxyacetophenone (1.68 g, 12.39 mrrtol) in tetrahydrofuran (120 mi) under argon was cooled to -78C and treated dropwise with lithium hexamethyldisilazane (1 M in tetrahydrofuran, 2.25 ml, 2.25 mmol). The solution was stirred at -78C for 1 hour and at -10C for 2 hours then cooled down to -78C and treated dropwise with a solution of 4- efhy.-5-nitro-pyridine-2-carboxylic acid methyl ester (WO2005/103003) (2.42 g, 12.39 mmo.) in tetrahydrofuran (60 ml). The dark red solution was stirred at -78C for 1 hour then at room temperature for 18 hours. The mixture was poured into a ice-cold 1 N solution of hydrochloric acid (200 ml) and extracted several times with ethyl acetate. The combined extracts were dried over sodium sulfate and concentrated to dryness. The residue was dissolved in acetic acid (60 ml), treated with sulfuric acid (0.33 ml) and heated to 100X for 30 minutes. After cooling to room temperature, the solution was concentrated and the residue added with water and neutralized with a saturated solution of sodium hydrogenocarbonate. The precipitate was filtrated, washed with water and dried under vacuum to yield 2-(4- Methyl-5-nitro-pyridin-2-yl)-chromen-4-one (2.33 g, 66%) as a brown solid. The previous chromen-4-none (770 mg, 2.72 mmol) was treated with tert-buty.- hydroxylamine hydrochloride (685 mg, 5.45 mmol) in methanol (20 ml) at 130C for 30 minutes under microwave irradiation (method D, step 1) to yield the title compound (394 mg, 41 %) after purification by silica ge. flash chromatography (gradient cyciohexane/dichloromethane 0-80%) as a gold solid.1 H NMR: (300 MHz) DMSO-d6 delta (ppm): 9.23 (s, 1 H), 8,08 (dd, J = 7.9 Hz, J = 1.7 Hz, 1 H), 7.89 (s, 1 H), 7.78 (s, 1 H), 7.42 (td, J = 7.6 Hz, J = 1.7 Hz, 1 H), 7.32-7.19 (m, 2H), 2.76 (s, 3H), 1.42 (s, 9H).

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, 868551-30-8, Methyl 4-methyl-5-nitropicolinate.

Reference:
Patent; DOMAIN THERAPEUTICS; PRESTWICK CHEMICAL, INC.; SCHANN, Stephan; MAYER, Stanislas; MORICE, Christophe; GIETHLEN, Bruno; WO2011/51478; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 628691-93-0, 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.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.

1.15.1. Step i: tert-butyl N-(2-chloro-3-fluoro-4-pyridyl)carbamate1002621 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 110C for 4 h. Mixture was diluted with H20 and extracted with DCM. The organic layer was dried (Na2SO4) and concentrated. The residue was purified by flash column chromatography (Si02, 100:0 to 80:20 DCM/EtOAc) to yield the desired product tert-butyl N-(2-chloro- 3 -fluoro-4-pyridyl)carbamate.

The chemical industry reduces the impact on the environment during synthesis 628691-93-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GALAPAGOS NV; MENET, Christel, Jeanne, Marie; MAMMOLITI, Oscar; BLANC, Javier; OR?ULIC, Mislav; RO?CIC, Maja; WO2015/110378; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 6318-51-0, Adding some certain compound to certain chemical reactions, such as: 6318-51-0, name is (4-Chlorophenyl)(pyridin-2-yl)methanone,molecular formula is C12H8ClNO, 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 6318-51-0.

General procedure: Six variants with significantly improved activity were selected to test their stereoselectivity and conversion rate. Bioconversion was conducted with 20mM 1a-9a, 20UmL-1 KpADH or variants in PBS buffer (pH 7.0, 100mM) in total volume of 2mL at 30C and 180rpm overnight. Then, 1mL of the reaction mixture was withdrawn and extracted with equal volume of ethyl acetate. The organic phase was isolated by centrifugation at 12000×g for 2min, and dried over anhydrous MgSO4. The conversion rate and stereoselectivity of the products were determined using the Agilent 1100 equipped with a Chiralcel OB-H column or a Chiralcel OD-H column (0.46mm×250mm×5mum, Diacel, Japan). Detailed conditions for stereoselectivity analysis and the retention times of (R)- and (S)-alcohols could be found in Table S3 [28].

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. 6318-51-0, (4-Chlorophenyl)(pyridin-2-yl)methanone, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Xu, Guochao; Dai, Wei; Wang, Yue; Zhang, Lu; Sun, Zewen; Zhou, Jieyu; Ni, Ye; Molecular catalysis; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 67058-77-9 , The common heterocyclic compound, 67058-77-9, name is 3-Nitro-1H-pyrrolo[2,3-c]pyridine, molecular formula is C7H5N3O2, 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.

To a solution of 3 -nitro- 1H-pyrrolo [2,3 -c]pyridine (250 mg, 1.53 mmol) in DIVIF (5 mL) was added NaH (60% dispersion in mineral oil, 61 mg, 1.53 mmol). After stirred at 0 C for 10 mm, the mixture was added dimethylsulfate (193 mg, 1.53 mmol) dropwise. After stirred at 0 C for 3 hrs, the mixture was partitioned in a mixture of H20 (50 mL) and EA (50 mL). The aqueous phase was then extracted by EA (50 mL x 2). Organic phase was combined, dried over anhydrous Na2SO4, and evaporated in vacuum. The residue was washed with MeOH (5 mL) to afford 6-methyl- 3-nitro-6H-pyrrolo[2,3-c]pyridine (70 mg, 26%) as a yellow solid. ?H NIVIR (400 IVIHz, DMSO-d6):oe = 9.09 (s, 1H), 8.65 (s, 1H), 8.25 (dd, J 6.8, 1.2 Hz, 1H), 8.14 (d, J= 6.8 Hz, 1H), 4.26 (s, 3H). MS: m/z 178.0 (M+H).

The synthetic route of 67058-77-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; GARDELL, Stephen; PINKERTON, Anthony B.; SERGIENKO, Eduard; SESSIONS, Hampton; (428 pag.)WO2018/132372; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89510-90-7, 2-Chloro-5-fluoro-4-pyridinamine, 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, Recommanded Product: 89510-90-7, blongs to pyridine-derivatives compound. Recommanded Product: 89510-90-7

Intermediate 11A was synthesized employing the procedure described for Example 7C (Scheme 7). The crude compound was purified by silica gel column chromatography eluted with 55% Ethylacetate in Hexane to afford hA (120 mg, 0.112 mmol, 19.3 % yield) as a off white solid. LCMS: m/z 622.7(M+H); rt 1.60 mm;10 Conditions B.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89510-90-7, 2-Chloro-5-fluoro-4-pyridinamine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HARIKRISHNAN, Lalgudi S.; FINK, Brian E.; BORZILLERI, Robert M.; TONUKUNURU, Gopikishan; WARRIER, Jayakumar Sankara; (111 pag.)WO2017/19757; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 13445-16-4, name is 3-Bromo-2,6-dimethoxypyridine, the common compound, a new synthetic route is introduced below. SDS of cas: 13445-16-4

EXAMPLE 1 Preparation of 2,6-dimethoxy-3-bromo-4-(diphenylphosphino)pyridine To a magnetically stirred solution of 4.0 mL of approximatly 2.0M LDA solution (in hexane) (7.98 mmol) was added a solution of 2,6-dimethoxyl-3-bromopyridine (3.14 g, 6.14 mmol) in 10 mL of THF at -78 C. over a period 20 minutes while the internal temperature was kept below -78 C. To the resulting red-brown suspension was added a solution of chlorodiphenylphosphine (1.20 mL, 6.75 mmol) in the 10 mL of THF at -78 C. The reaction mixture was allowed to warm to ambient temperature overnight and was poured into 20 mL water. The organic product was extracted with dichloromethane (3*20 mL). The combined extract was dried with anhydrous magnesium sulfate and was concentrated in vaccuo to give a crude product which was recrystallized in methanol to give 2.34 g of pure product (95% theoretical yield). 1 H-NMR(400 MHz): delta 3.83 (s, 3H, OCH3), 4.00 (s, 3H, OCH3), 5.71 (d, JPH =2.4 Hz, 1H, PyH’s), 7.38~7.28 (m, 10H, PhH’s). 31 P-NMR(161 MHz): delta-4.18 ppm. 13 C-NMR(101 MHz): delta 53.61, 54.48, 101.73 (J=27.8 Hz), 106.52 (J=2.1 Hz), 128.76 (J=7.6 Hz), 129.38, 134.07, 134.27, 134.33, 134.43, 154.13 (J=16.0 Hz), 158.62 (J=5.6 Hz), 161.5. mass spectrum (high resolution): M.W.=401.0, consistent with C19 H17 NPBrO2, melting point: 149.7~150.8 C.

The synthetic route of 13445-16-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Hong Kong Polytechnic University; US5886182; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 16744-81-3 ,Some common heterocyclic compound, 16744-81-3, molecular formula is C7H7NO2, 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.

D1. METHVL3- (4-METHOXVPVRIDIN-2-Y ACRVLATE; A mixture of 45 g OF 4-METHOXYPYRIDINE-2-CARBALDEHYDE (Ashimori et AL., Chem. Pharm. Bull. 38,2446- 2458 (1990) ), 75.80 g of pyridine hydrochloride, 102.45 g of monomethyl malonate potassium salt and 4.1 ml of piperidine in 700 ml of pyridine are slowly heated, with stirring, to 120°C. When the evolution of gas starts, the heating source is temporarily removed to stop the reaction from becoming too violent. Once the reaction has subsided, the mixture is stirred at 120°C for a further 2.5 hours, and the pyridine is then distilled off under reduced pressure. The residue is partitioned between ethyl ACETATE/WATER and the organic phase is washed with water and dried. The residue obtained after concentration is chromatographed on a silica gel column using ethyl acetate/petroleum ether 2: 1. This initially gives 43.2 g of the title compound as a yellow oil which crystallizes on standing and then shows a m. p. of 80-82°C. The mass spectrum shows the molecular peak MH+ at 194 Da

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. 16744-81-3, 4-Methoxypicolinaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ALTANA PHARMA AG; WO2005/30769; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem