Month: April 2022

Synthetic Route of 103058-87-3, 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 103058-87-3, name is 5-Bromo-2-methoxynicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

Reference Example 1; 4- (5-formgammal-6-methoxypyridin-3-gammal) benzonitrile; A mixture of 5-bromo-2-methoxynicotinaldehyde (2.0 g) synthesized by a known method (Journal of Heterocyclic Chemistry 1985, 22(6), 1583-1592), (4- cyanophenyl) boronic acid (1.36 g) , Pd(PPh3)4 (0.32 g) and potassium carbonate (2.6 g) in THF (20 mL) and water (10 mL) was heated under reflux for 12 hrs. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and concentrated under reduced pressure. The obtained residue was crystallized from acetone/ethanol/IPE to give the title compound (0.93 g) as white crystals . melting point: 157C

According to the analysis of related databases, 103058-87-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2007/89031; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 92138-35-7, 6-Chloro-3-nitropyridin-2(1H)-one, 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 92138-35-7, blongs to pyridine-derivatives compound. Product Details of 92138-35-7

100 L jacketed reactor equipped with a temperature probe, nitrogen inlet and reflux condenser was charged with toluene (27.0 L, 30 vol.) and EtOH (5.4 L, 6 vol.) followed by 6-chloro-3-nitropyridin-2(1H)-one (900.0 g, 5.15 mol) and phenyl boronic acid (640.4 g, 5.253 mol). The mixture was stirred at ambient temperature for 15 minutes before a solution of K2CO3 (173.9 g, 11.33 mol) in DI water (5.4 L, 6 vol.) was added. The reaction mixture was degassed with argon for 30 minutes at room temperature. Tetrakis triphenylphosphine palladium (178.2 g, 3 mol %) was added and the solution was heated to 95-100 C. (internal temperature was 77-79 C.) and stirred for 3 hours. After 3 hours HPLC showed 2.8% of starting material and another single impurity (15.3%, 1.17 RRT). The reaction was maintained for 3 hours at same temperature. After 6 hours, there was no progress in the reaction and the mixture was cooled to room temperature, degassed for 30 minutes, and another 5.0 g of tetrakis triphenylphosphine palladium was added and the solution was heated to 95-100 C. Reaction was deemed complete after one hour by HPLC. The reaction mixture was cooled to room temperature, the reaction was diluted with DI water (11.7 L, 13 vol.) followed by EtOAc (18.0 L, 20 vol.) and stirred for 1 hour. The two layers were separated, leaving the solids in aqueous layer. The aqueous layer was extracted with EtOAc (13.5 L, 15 vol.). The combined aqueous layers were neutralized pH to 6.2-6.8 with 3N HCl, when more solids precipitated out, the solids were filtered off, washed with water (2×2.5 L, 5 vol.) and dried under vacuum at 45-50 C. for 48 hours, to furnish 1a (761.1 g, 68.9% yield, 78.0% purity) as yellow solid. The compound was characterized by 1H NMR (DMSO-d6) and MS. (0157) The combined organic (ethyl acetate) layers were extracted with 3N NaOH (15 L), when solids were formed. The organic layer was separated. The aqueous layer was then acidified pH to 5-6 with 3N HCl, when more solids were precipitated out, which were filtered off and washed with DI water (2.0 L) and dried to obtain compound 1a (140.0 g, 12.7%, 93.8% purity, 2nd crop).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,92138-35-7, 6-Chloro-3-nitropyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; ArQule, Inc.; Bates, Craig; Chen, Jian-Xie; Mao, Jianmin; Reed, David P.; US2015/266876; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 886365-06-6, Methyl 5-bromo-4-methylpicolinate, 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 886365-06-6, blongs to pyridine-derivatives compound. Product Details of 886365-06-6

Into a vial was weighed methyl 5-bromo-4-methylpicolinate (300 mg, 1.30 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)-dichloromethane complex (54.3 mg, 0.0652 mmol), bis(pinacolato)diboron (364 mg, 1.43 mmol), and potassium acetate (384 mg, 3.91 mmol). Under nitrogen, anhydrous 1,4-dioxane (6.5 mL) was added and the vial was sealed. The reaction mixture was stirred at 120 C. for 18 h. After cooling to rt, under nitrogen, to the reaction vessel was added (+-)-(trans)-N-(8-amino-6-chloro-2,7-naphthyridin-3-yl)-2-(1-methyl-1H-pyrazol-4-yl)cyclopropane-1-carboxamide (447 mg, 1.30 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)-dichloromethane complex (54.3 mg, 0.0652 mmol), and potassium carbonate (540 mg, 3.91 mmol), and water (1.3 mL). The vial was sealed and stirred at 100 C. for 23 h. The reaction mixture was concentrated to dryness and residue purified by flash column chromatography (CH2Cl2/MeOH, 100:0-85:15) to afford the target compound as a brown solid (126 mg, 21% over 2 steps); 1H NMR (400 MHz, DMSO-d6) delta 10.95 (s, 1H), 9.38 (s, 1H), 8.71 (s, 1H), 8.28 (s, 1H), 8.01 (s, 1H), 7.56 (s, 1H), 7.37 (br s, 2H), 7.29 (s, 1H), 7.05 (s, 1H), 3.91 (s, 3H), 3.77 (s, 3H), 2.25-2.16 (m, 2H), 1.90 (s, 3H), 1.43-1.34 (m, 1H), 1.24-1.14 (m, 1H).

The synthetic route of 886365-06-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Daniels, Blake; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Huestis, Malcolm; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Siu, Michael; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Gancia, Emanuela; Jones, Graham; Lainchbury, Michael; Madin, Andrew; Seward, Eileen; Favor, David; Fong, Kin Chiu; Good, Andrew; Hu, Yonghan; Hu, Baihua; Lu, Aijun; US2018/282328; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1620-71-9, 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.1620-71-9, name is 5-Methyl-2-(trifluoromethyl)pyridine, molecular formula is C7H6F3N, molecular weight is 161.12, as common compound, the synthetic route is as follows.

Step A: 5-methyl-2-(trifluoromethyl)pyridine 1-oxide 5-methyl-2-trifluoromethyl-pyridine (commercially available, 0.164g) was dissolved in dichloromethane (5 mL). Meta-chloroperoxybenzoic acid (m-CPBA, 0.486 g) was added, and the mixture was stirred 48 hours at ambient (rt) temperature. The solvent was remove under reduce pressure and the crude product was purified by chromatography (solvent: isohexane/diethyl ether 7/3 to diethylether) to give the title compound (120mg) as a white solid. 1H NMR (300MHz, CDCI3): oe (ppm) 8.17 (s, 1H), 7.57 (d,1H), 7.16 (d, 1H), 2.38 (s, 3H) ppm.

Statistics shows that 1620-71-9 is playing an increasingly important role. we look forward to future research findings about 5-Methyl-2-(trifluoromethyl)pyridine.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; HALL, Roger Graham; GOEGH, Tibor; JUNG, Pierre Joseph Marcel; EDMUNDS, Andrew; JEANGUENAT, Andre; MUEHLEBACH, Michel; STOLLER, Andre; (98 pag.)WO2016/20286; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 64951-08-2, Adding some certain compound to certain chemical reactions, such as: 64951-08-2, name is Imidazo[1,2-a]pyridine-2-carboxylic acid,molecular formula is C8H6N2O2, 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 64951-08-2.

A mixture of 3-(cis-4-aminocyclohexyl)-6-fluoro-l-(tetrahydro-2H-thiopyran-4- yl)pyrido[2,3-d]pyrimidine-2,4(lH,3H)-dione hydrochloride (600 mg, 1.5 mmol), imidazo[l52-a]pyridme-2-carboxylic acid (292 mg, 1.8 mmol), HATU (685 mg, 1.8 mmol), and DIEA (1.02 ml, 6 mmol) in nuMP (80 ml) was stirred for 1 h at room temperature (at pH 8-9). Ethyl acetate was added and the crude product was washed twice with aqueous sodium hydrogencarbonate, 0.5 M aqueous citric acid and water. The organic solvents dried over nua2SO4, filtrated and removed in vacuum. The residue was recrystallised in ethyl acetate (5 ml) to give the title compound (750 mg, 96%). 1H nuMR (400 MHz, DMSCW6): delta 8.79 (IH, d); 8.68 (IH, d); 8.52 (IH, s); 8.25(IH, dd); 7.94 (IH, brs); 7.75 (IH, d); 7.49 (IH, t); 7.10 (IH, t); 5.22 (IH, brs); 4.84 (IH, t); 4.16 (IH, s); 2.84-2.69 (6H, m); 2.61 (2H, q); 1.99 (4H, m); 1.71 (2H, t); 1.57 (2H, brd) APCI-MS m/z: 523 [MH+].

According to the analysis of related databases, 64951-08-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; WO2007/108750; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 16744-81-3, 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 16744-81-3, name is 4-Methoxypicolinaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

D1. METHYL 3- (4-METHOXVAVRIDIN-2-VL) 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 mi of piperidine in 700 mi 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.

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 16744-81-3, 4-Methoxypicolinaldehyde.

Reference:
Patent; ALTANA PHARMA AG; WO2005/30771; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 69045-78-9, Adding some certain compound to certain chemical reactions, such as: 69045-78-9, name is 2-Chloro-5-(trichloromethyl)pyridine,molecular formula is C6H3Cl4N, 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 69045-78-9.

(Method B) In 11 ml of nitrobenzene were dissolved 0.69 g of 2-chloro-5-trichloromethylpyridine and 0.62 g of veratrole, to which 1 g of zinc chloride and 0.3 ml of dimethylformamide were added with stirring. After stirring at 70 C. for 12 hours, 10 ml 1N HCl was added to the reaction mixture, and the mixture was stirred at 50 to 60 C. for 30 minutes. After cooling to room temperature, the reaction mixture was extracted with dichloromethane. The extracts were dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silicagel column chromatography [eluted with a mixture solvent of dichloromethane and diethyl ether (10:1)], to give 0.56 g of 2-chloro-5-(3,4-dimethoxybenzoyl)pyridine mp 158-159 C.

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. 69045-78-9, 2-Chloro-5-(trichloromethyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US4954497; (1990); A;,
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.184416-84-0, name is 2,3-Dichloroisonicotinic acid, molecular formula is C6H3Cl2NO2, molecular weight is 192, as common compound, the synthetic route is as follows.category: pyridine-derivatives

To a solution of 2,3-dichloroisonicotinic acid (5.62 mmol) in 15 mL DMF were added NaH (7.31 mmol) followed by iodoethane (6.75 mmol) at 0C. The cooling bath was removed and the mixture was stirred at RT overnight. The reaction was quenched with sat. aq. NaHC03 solution and extracted with EtOAc. The combined organic layers were dried over MgS04 and concentrated in vacuo. Purification by CC (KP-SIL from Biotage) using Hept/EtOAc (6/4) gives the desired product as yellow oil; LC-MS (A): tR = 0.78 min; [M+H]+: 219.95.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,184416-84-0, 2,3-Dichloroisonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; HILPERT, Kurt; HUBLER, Francis; KIMMERLIN, Thierry; MURPHY, Mark; RENNEBERG, Dorte; STAMM, Simon; WO2013/14587; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 79055-59-7, name is 2-Bromo-6-methylpyridin-4-amine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 79055-59-7

EXAMPLE 36 2-(7-Chloro-3,4-dihydro-naphthalen-2-yl)-6-methyl-pyridin-4-yl-amine fumarate Following the general method described in example 19, the title compound was obtained as a white crystalline material by reaction of 2-bromo-6-methyl-pyridin-4-ylamine (cf example 26c) with palladium tetrakis(triphenylphosphine), 7-chloro-3,4-dihydro-naphthalene-2-boronic acid (cf example 30b) and aqueous 2M K2CO3 and crystallization of the free base as the fumarate salt. Mp. 232-233 C. (MeOH), MS: m/e=285 (M+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, 79055-59-7, 2-Bromo-6-methylpyridin-4-amine.

Reference:
Patent; Alanine, Alexander; Buettelmann, Bernd; Heitz Neidhart, Marie-Paule; Pinard, Emmanuel; Wyler, Rene; US2003/144525; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1440519-73-2, 2-Chloro-6-(4-methoxybenzyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one, 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, Quality Control of 2-Chloro-6-(4-methoxybenzyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one, blongs to pyridine-derivatives compound. Quality Control of 2-Chloro-6-(4-methoxybenzyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one

General procedure: Procedure A: To a solution of 5-bromo-2-(4-methoxybenzyl)isoindolin-1-one (1, 0.5 g, 1.5 mmol) in dioxane (10 mL) was added 7H-pyrrolo[2,3-d]pyrimidine (2, 0.27 g, 2.25 mmol) and potassium tert-butoxide (0.51 g, 4.52 mmol) followed by the addition of XantPhos (0.087 g, 0.15 mmol). The reaction mixture was degassed with argon for 15 min. Tris(dibenzylideneacetone)dipalladium(0) (0.14 g, 0.15 mmol) was then added and the reaction mixture was heated at 90 C. and maintained at that temperature for 12 h. (0193) Following heating, the reaction mixture was cooled and concentrated under reduced pressure. The concentrated reaction mixture was extracted in ethyl acetate. The organic layer was separated, dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue obtained was purified by silica gel (100-200 mesh) column chromatography using 5% methanol in dichloromethane as eluent so as to afford 2-(4-methoxybenzyl)-5-(7H-pyrrolo[2,3-d]pyrimidin-7-yl)isoindolin-1-one (3). Yield: 0.21 g, 38%;

The synthetic route of 1440519-73-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EFFECTOR THERAPEUTICS, INC.; Sprengeler, Paul A.; Reich, Siegfried H.; Ernst, Justin T.; Webber, Stephen E.; (55 pag.)US2017/121339; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem