Month: July 2021

Related Products of 1101120-05-1, 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. 1101120-05-1, name is 3-Formylpyrazolo[1,5-a]pyridine-5-carbonitrile, molecular formula is C9H5N3O, 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.

General procedure: These were made using NaHCO3 or 2,6-lutidine as detailed below, unless otherwise stated. Methylhydrazine sulfate (1.2 equiv) and NaHCO3 (5 equiv) were added to a solution of 3-formylpyrazolo[1,5-a]pyridine-5-carbonitrile (2) (1 equiv) in MeOH (5 mL). After all of the aldehyde was consumed, sulfonyl chloride or acyl chloride (1.3 equiv) was added and the reaction mixture stirred for a further 30 min. The solvent was removed in vacuo and the residue taken up in CH2Cl2 and water. The layers were separated and the aqueous phase extracted with CH2Cl2, then the combined organic layers were dried (Na2SO4) and the solvent removed in vacuo. Chromatography or trituration then afforded the hydrazides. Alternatively, methylhydrazine sulfate (1.2 equiv) and 2,6-lutidine (5 equiv) were added to a solution of 2 (1 equiv) in MeOH (5 mL). After all of the aldehyde was consumed, sulfonyl chloride or acyl chloride (1.3 equiv) was added and the reaction mixture stirred for a further 30 min. The hydrazide was then filtered off, washed with MeOH and dried.

According to the analysis of related databases, 1101120-05-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kendall, Jackie D.; Giddens, Anna C.; Tsang, Kit Yee; Frederick, Raphael; Marshall, Elaine S.; Singh, Ripudaman; Lill, Claire L.; Lee, Woo-Jeong; Kolekar, Sharada; Chao, Mindy; Malik, Alisha; Yu, Shuqiao; Chaussade, Claire; Buchanan, Christina; Rewcastle, Gordon W.; Baguley, Bruce C.; Flanagan, Jack U.; Jamieson, Stephen M.F.; Denny, William A.; Shepherd, Peter R.; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 58 – 68;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 66572-56-3, Adding some certain compound to certain chemical reactions, such as: 66572-56-3, name is 2-Bromoisonicotinic acid,molecular formula is C6H4BrNO2, 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 66572-56-3.

A solution of 2-bromoisonicotinic acid (5.00 g, 24.8 mmol) in MeOH (50 mL) was treated with sulfuric acid (0.50 mL, 9.4 mmol) and the reaction mixture was stirred at 80 C for 1 hour. The mixture was returned to room temperature and stirred for a further 96 hours before heating to 80 C and stirring for 24 hours. The reaction mixture was cooled to room temperature, and the volatiles were removed in vacuo. An aqueous NaOH solution (2 M, -50 mL) was added to the residue and the aqueous was extracted with EtOAc (3 * 50 mL). The organic layers were combined, washed with brine, dried (MgS04) and the solvent removed in vacuo to give the title compound as a yellow oil (4.14 g, 77%). LCMS-B: rt 3.55 min; m/z 216 [Mu+Eta for /9Br. 218 [M+H]+ for 81 Br; 1H NMR (400 MHz, CDCb) delta 8.52 (dd, J = 5.0, 0.8 Hz, 1 H), 8.04 (t, J = 1.2 Hz. 1 H), 7.80 (dd, J = 5.0, 1.4 Hz, 1 H), 3.96 (s, 3H).

According to the analysis of related databases, 66572-56-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CTXT PTY LTD; FOITZIK, Richard Charles; CAMERINO, Michelle Ang; WALKER, Scott Raymond; LAGIAKOS, H. Rachel; (98 pag.)WO2016/34675; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 100367-39-3, 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. 100367-39-3, name is 4-Bromo-2-methoxypyridine, molecular formula is C6H6BrNO, 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.

4-BromoBromo-2-methoxypyridine (3.06 g, 16.2 mmol), (6- (trifluoromethyl)pyridin-3-yl)methanol (2.74 g, 15.5 mmol), 3,4,7,8- tetramethylphenanthroline (0.36 g, 0.15 mmol), CuI (0.14 g, 0.74 mmol) and Cs2CO3 (7.57 g, 23.2 mmol) were combined in toluene (15 mL) and heated to reflux under a nitrogen Attorney’s Docket 2882.023B atmosphere for 16 h. Upon cooling the mixture was purified by flash column chromagraphy (silica gel, hexanes/EtOAc, 1 :0 to 1 :1) to provide the title compound (3.19 g, 72%) as a red oil: 1H NMR (300 MHz, CDCl3) delta 8.78 (s, IH), 8.02 (d, J= 5.9 Hz, IH), 7.95 (d, J= 8.1 Hz, IH), 7.32 (d, J= 8.0 Hz, IH), 6.55 (dd, J= 5.9, 2.2 Hz, IH), 6.26 (d, J = 2.2 Hz, IH), 5.16 (s, 2H), 3.93 (s, 3H).

According to the analysis of related databases, 100367-39-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALBANY MOLECULAR RESEARCH, INC.; WO2009/89482; (2009); 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. 1289197-78-9, name is 2-Bromo-4-chloronicotinaldehyde, the common compound, a new synthetic route is introduced below. Safety of 2-Bromo-4-chloronicotinaldehyde

Example 170b 4-Chloro-2-[(1R,11S)-7-oxo-3,6-diazatetracyclo[9.2.1.02,10.03,8]tetradeca-2(10),8-dien-6-yl]pyridine-3-carbaldehyde 170b A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 1,4-dioxane (30 mL), (1S,11R)-3,6-diazatetracyclo[9.2.1.02,10.03,8]tetradeca-2(10),8-dien-7-one 170a (400 mg, 2.0 mmol), 2-bromo-4-chloronicotinaldehyde 103a (1.30 g, 6.0 mmol), and potassium acetate (390 mg, 4.0 mmol). After bubbling nitrogen through the resulting mixture for 30 minutes, Xantphos (110 mg, 0.20 mmol) and tris(dibenzylideneacetone)dipalladium(0) (180 mg, 0.20 mmol) were added, and the reaction mixture was heated at 80 C for 10 h. After this time the reaction was cooled to room temperature and filtered. The filtrate was partitioned between ethyl acetate (50 mL) and water (30 mL). The aqueous layer was separated and extracted with ethyl acetate (3 X 30 mL). The combined organic layer was washed with brine (20 mL) and dried over sodium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 2:1 petroleum ether/ethyl acetate to afford 170b (405 mg, 59%) as a yellow solid. MS-ESI: [M+H]+ 342.2

The synthetic route of 1289197-78-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F.Hoffmann-La Roche AG; CRAWFORD, James John; ORTWINE, Daniel Fred; WEI, BinQing; YOUNG, Wendy B.; EP2773638; (2015); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 861673-68-9, 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. 861673-68-9, name is 2-(2-(tert-Butyl)phenoxy)pyridin-3-amine, molecular formula is C15H18N2O, 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.

A mixture of 2-(2-tert-Butylphenoxy)-3-aminopyridine (Intermediate 1) (50 mg, 0.20 mmol) and 2-methylbenzoyl isothiocyanate (36 muL, 0.24 mmol, 1.2 eq) in DCM (10 mL) was heated at reflux for 1 h. The mixture was cooled to rt and evaporated to give the crude product. Purification by flash chromatography (silica, 0-20% EtOAc/hexane gradient) provided Example 423a (91 mg) as white crystals. (M+H)+=420.25.

According to the analysis of related databases, 861673-68-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sutton, James C.; Pi, Zulan; Ruel, Rejean; L’Heureux, Alexandre; Thibeault, Carl; Lam, Patrick Y. S.; US2006/173002; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 65-22-5, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 65-22-5 as follows.

General procedure: The ligands L3, L4, L5 and L6 were synthesized using pyridoxal hydrochloride (0.180g, 8mmol) solubilized in methanol (15mL). Then 4-hydroxybenzoic hydrazide (L3), 4-methoxybenzoic hydrazide (L4), 4-aminobenzoic hydrazide (L5), and 4-nitrobenzoic hydrazide (L6) were added (0.134g, 0.146g, 0.133g, 0.160g, 8mmol each, respectively). The reaction solution remained at 50C and constant stirring, with reaction time of 2h (L3-L4) and 3h (L5-L6). After this period, the reaction mixture was cooled to room temperature and the methanol was then evaporated under reduced pressure, whereby a yellow solid was obtained (Scheme 2 ). Thin-layer chromatography plates monitored the reactions (Hex/Ac 80-20). The synthetic route used to obtain the L4 ligand is similar to that proposed by K. Ramdasand and co-workers [29].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,65-22-5, its application will become more common.

Reference:
Article; Arantes, Leticia Priscilla; Back, Davi Fernando; Chaves, Otavio Augusto; Iglesias, Bernardo Almeida; Neves, Ademir; Piquini, Paulo Cesar; Siqueira, Josieli Demetrio; Soares, Felix Antunes; de Pellegrin, Sidnei Flores; dos Santos, Sailer Santos; Journal of Inorganic Biochemistry; vol. 204; (2020);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 156270-06-3, 1H-Pyrrolo[2,3-b]pyridine-3-carboxylicacid, 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 1H-Pyrrolo[2,3-b]pyridine-3-carboxylicacid, blongs to pyridine-derivatives compound. Application In Synthesis of 1H-Pyrrolo[2,3-b]pyridine-3-carboxylicacid

General procedure: Respective benzoic acid derivatives 5-chloro-2-methoxybenzoic acid or 13a-h (1 eq) were dissolved in anhydrous DMF, then EDCI (1.5eq), HOBT (1.5 eq) and DIEA (2.0 eq) were added successively. After the mixture was stirred at room temperature for 0.5?1h, the respective amine derivatives 3, 6 or 10 (1 eq) were added. The reaction mixture was stirred at room temperature overnight (or 12h). After the TLC showed the disappearance of the starting materials, water was added and the resulting suspension was filtered using a buchner funnel, and the precipitate was washed with water and then dried to give white solid powder. Products were further purified by flash column chromatography.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,156270-06-3, 1H-Pyrrolo[2,3-b]pyridine-3-carboxylicacid, and friends who are interested can also refer to it.

Reference:
Article; Yuan, Zigao; Sun, Qinsheng; Li, Dan; Miao, Shuangshuang; Chen, Shaopeng; Song, Lu; Gao, Chunmei; Chen, Yuzong; Tan, Chunyan; Jiang, Yuyang; European Journal of Medicinal Chemistry; vol. 134; (2017); p. 281 – 292;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 56622-54-9, 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. 56622-54-9, name is (6-Methylpyridin-3-yl)methanamine, molecular formula is C7H10N2, 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 5-(ethoxycarbonyl)-4′-methylbiphenyl-3-carboxylic acid (1.5 g, 5.3 mmol), N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (2.0 g, 10 mmol), 1- hydroxybenzotriazole hydrate (0.32 g, 2.1 mmol), and CH2Cl2 (50 mL) were added (6-methylpyridin-3- yl)methanamine (0.97 g, 7.9 mmol) and NN-diisopropylethylamine (1.8 mL, 10 mmol). The mixture was stirred at room temperature for 4h, and then washed with water and aq. Na2CO3 solution, dried (Na2SO4), and concentrated in vacuo. The residue was purified by silica gel column to afford a white foam. LC-MS: 389.4 [M+l]+; 1H NMR (400 MHz, CDCl3): 8.53 (d, IH, J = 2.0 Hz), 8.39 (t, IH, J = 1.6 Hz), 8.29 (t, IH, J = 1.6 Hz), 8.26 (t, IH, J = 1.6 Hz), 7.66 (dd, IH, J = 8.0, 2.0 Hz), 7.55 (d, 2H, J = 8.4 Hz), 7.28 (d, 2H, J = 8.0 Hz), 7.17 (d, IH, J = 8.0 Hz), 6.64 (m, IH), 4.67 (d, 2H, J = 5.6 Hz), 4.42 (q, 2H, J = 7.2 Hz), 2.57 (s, 3H), 2.41 (s, 3H), 1.42 (t, 3H, J = 7.2 Hz).

According to the analysis of related databases, 56622-54-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RENOVIS, INC.; WO2009/110985; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 76093-33-9 ,Some common heterocyclic compound, 76093-33-9, molecular formula is C16H16N2O6, 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 (R)-5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid (4.86g, 14.6mmol) in dichloromethane was added 0.1mL DMF. To the mixture was slowly added oxalyl chloride (3.68g, 29.0mmol) dropwisely in an ice bath. The reaction was conducted at 25C until the completion of reaction. The resulting mixture was evaporated under reduced pressure to remove oxalyl chloride. To the reaction flask were slowly added dichloromethane (20mL), the crude product of 1-(3,5-difluorobenzyl)-3-methylpyrrolidin-3-ol (1.8g) and DIPEA (1.86g, 14.4mmol) dropwisely under cooling in an ice bath respectively and successively. The reaction was conducted at 25C. After the completion of reaction monitored by HPLC, the reaction solution was washed with water thrice. The organic phase was dried over sodium sulfate, and filtered by suction. The filtrate was evaporated to dryness, and purified by column chromatography (silica gel column, eluted with petroleum ether: ethyl acetate = 85:1 (volumetric ratio)) to produce (4S)-3-[1-(3,5-difluorobenzyl)-3-methyl-3-pyrrolidin-3-yl] 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate (1.78 g) in a yield of 45.6% (two steps together). Molecular formula: C28H29F2N3O6 Mw: 541.2 MS (M+H): 543.3 1H-NMR(DMSO, 400 MHz) delta: 9.14 (1 H, t), 8.02-7.97 (2 H, m), 7.60-7.55 (2 H, m), 7.39-7.33 (2 H, m), 4.93-4.90 (1 H, d), 4.41-4.40 (2 H, m), 3.56-3.53 (6 H, m), 3.35 (1 H, s), 3.07 (1 H, s), 2.30-2.26 (6 H, m), 1.50-1.24 (3 H, dd), 1.10 (3 H, 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. 76093-33-9, (R)-5-(Methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; ZHANG, Hui; FAN, Mingwei; SUN, Liang; EP2703398; (2014); 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. 86873-60-1, name is 5-Chloro-2-picolinic acid, the common compound, a new synthetic route is introduced below. Safety of 5-Chloro-2-picolinic acid

A solution of 5-chloro-pyridine-2-carboxylic acid (0.136 g, 0.86 mmol) in dichloromethane (15 ml), was treated with Huenig’s base (0.30 ml, 1.73 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (HATU) (0.328 g, 0.86 mmol) at room temperature. After 15 minutes of stirring, (RS)-5-(5-amino-2-fluoro-phenyl)-5-cyclopropyl-morpholine-3-thione (0.177 g, 0.66 mmol) was added and stirring continued for one hour. For the workup, the light yellow solution was poured on an ice-cold saturated solution of sodium hydrogen-carbonate, then extracted twice with dichloromethane. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated. The residue was purified by chromatography on silica gel using a 9:1-mixture of dichloromethane and ethyl acetate as the eluent. The 5-Chloro-pyridine-2-carboxylic acid [3-((RS)-3-cyclopropyl-5-thioxo-morpholin-3-yl)-4-fluoro-phenyl]-amide was obtained as an off-white solid (0.245 g, 90% of theory). Mass (calculated) C19H17ClFN3O2S [405.879]; (found) [M+H]+=406.

The synthetic route of 86873-60-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Andreini, Matteo; Banner, David; Guba, Wolfgang; Hilpert, Hans; Mauser, Harald; Mayweg, Alexander V.; Narquizian, Robert; Power, Eoin; Roger-Evans, Mark; Travagli, Massimiliano; Valacchi, Michela; Woltering, Thomas; Wostl, Wolfgang; US2011/46122; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem