Month: April 2022

Reference of 845306-04-9, 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 845306-04-9, name is 6-Chloro-N-methylpicolinamide. This compound has unique chemical properties. The synthetic route is as follows.

A stirred solution of Intermediate 2 (0.6g, 1.91 mmol) in dry 1 ,4-dioxane (10 mL), was added cesium carbonate (1.9g, 5.88 mmol) followed by 6-chloro-N-methylpicolinamide (0.25 g, 1.47 mmol, ABCR). Nitrogen was flushed into the solution for 20 min and Pd(OAc)2 (0.016 g, 0.07 mmol) and 2-2′-bis (diphenylphosphino)-1,1′-binaphthyl (0.091 g, 0.14 mmol) were added. The reaction mixture was stirred at 100 C for 12 h. The resulting reaction mixture was filtered through celite and evaporated under vacuum. Water (5 mL) was added and the mixture was extracted with EtOAc (50mL). The organic layer was dried over anhydrous Na2SO4 and evaporated. The resulting crude product was purified by column chromatography ( brown solid). 1H NMR (400 MHz, DMSO-d6): delta 8.94-8.92 (m, 2H), 8.41 (d, J = 4.0 Hz, 1 H), 8.09 (d, J = 8.8 Hz, 1 H), 8.01 (s, 1 H), 7.94-7.94 (m, 1 H), 7.63 (t, J = 8.4 Hz, 1 H), 7.25-7.23 (m, 1 H), 6.94 (d, J = 8.4 Hz, 1 H), 3.79-3.77 (m, 1 H), 3.58-3.58 (m, 4H), 2.77 (d, J = 4.80 Hz, 3H), 2.59-2.58 (m, 2H), 2.49-2.45 (m, 2H), 1.45 (d, J = 6.80 Hz, 3H). LCMS: (Method A) 377.2 (M +H), Rt. 2.14min, 95.23% (Max). HPLC: (Method A) Rt. 2.07min, 96.75% (Max).

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 845306-04-9, 6-Chloro-N-methylpicolinamide.

Reference:
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; KULKARNI, Santosh, S.; GIRI, Awadut Gajendra; (247 pag.)WO2017/144639; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 56673-34-8, Adding some certain compound to certain chemical reactions, such as: 56673-34-8, name is 3-Bromo-6-mercaptopyridine,molecular formula is C5H4BrNS, 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 56673-34-8.

To a solution of 5-bromopyridine-2-thiol (3.9 g) in THF (100 ml_) was added NaH (1 .24 g) at 0C and the mixture was stirred at 0C for 0.5 h. Then (bromomethyl)cyclopropane (2.79 g) was added. The mixture was allowed to warm to r.t. and stirred for 6 hours. Themixture was poured into ice water (200 ml_) and extracted with EA (100 ml_ x 3). The combined organic phases were washed with brine (50 ml_) and then dried over Na2SO4. After filtration and evaporation of the solvent, the residue was purified by SGC (eluent: PE) to provide the subtitle compound. MS ESI+: m/z = 244 [M+H]+.

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. 56673-34-8, 3-Bromo-6-mercaptopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SANOFI; SCHWINK, Lothar; BOSSART, Martin; GLOMBIK, Heiner; GOSSEL, Matthias; KADEREIT, Dieter; KLABUNDE, Thomas; MAIER, Thomas; STENGELIN, Siegfried; WO2014/56938; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 887115-56-2, 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.887115-56-2, name is 5-Bromo-1-methyl-1H-pyrazolo[3,4-b]pyridine, molecular formula is C7H6BrN3, molecular weight is 212.05, as common compound, the synthetic route is as follows.

Compound 1 (1.72 g, 8.11 mmol) was dissolved in DMF (20 mL) under nitrogen atmosphere, and bis(pinacolato)diboron (4.12 g, 16.2 mmol), potassium acetate (2.39 g, 24.3 mmol), and a dichloromethane adduct of [1,1?-bis(diphenylphosphino)ferrocene]palladium (II) dichloride (0.331 g, 0.406 mmol) were added thereto, followed by stirring at 90Cfor 12 hours.After the resultant reaction solution was allowed to cool, water was added thereto, followed by extraction withethyl acetate twice. The organic layer was washed with water twice and dried over anhydrous sodium sulfate, and thesolvent was distilled off under reduced pressure.The thus obtained residue was dissolved in 1,4-dioxane/water (2/1) (30 mL), and Compound V (synthesizedin accordance with the method described in WO2012/158413) (2.60 g, 8.10 mmol), tripotassium phosphate (3.44 g, 16.2mmol), chloro(2,4,6-triisopropyl-2?-dicyclohexylphosphino-biphenyl)[2-(2?-amino-1,1?-biphenyl]palladium (II) (0.128 g,0.162 mmol) were added thereto, followed by stirring at 90C for 4 hours.After the resultant reaction solution was allowed to cool, a brine was added thereto, followed by the extractionwith ethyl acetate twice, and then, the resultant was dried over anhydrous sodium sulfate, and the solvent was distilledoff under reduced pressure. The thus obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to giveCompound 2 (1.50 g, Yield 61%).1H-NMR (CDCl3) delta: 2.15 (s, 3H), 3.72 (s, 2H), 4.19 (s, 3H), 7.36-7.39 (m, 1H), 7.51 (t, J = 8.0Hz, 2H), 7.65 (d, J = 8.0Hz,2H), 8.03 (s, 1H), 8.35 (d, J = 1.6Hz, 1H), 8.93 (d, J = 1.6Hz, 1H).

Statistics shows that 887115-56-2 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-1-methyl-1H-pyrazolo[3,4-b]pyridine.

Reference:
Patent; Shionogi & Co., Ltd.; YUKIMASA, Akira; KANO, Kazuya; HORIGUCHI, Tohru; NAKAMURA, Kenichiroh; INOUE, Takatsugu; FUJIU, Motohiro; YAMAGUCHI, Hiroki; (156 pag.)EP3412663; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 19842-08-1, 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. 19842-08-1, name is 2-Bromo-5-ethylpyridine. A new synthetic method of this compound is introduced below.

To a stirred solution of 2-bromo-5-cyclopropylpyridine (1 g, 5 mmole) in CHC13(15 mL) was added mCPBA (1.7, 1.5 equiv). The reaction mixture was heated to 50 C. for 4 hours to complete the reaction. It was cooled and diluted with 20 mL DCM and washed with sat. NaHCO3 solution (5×15 mL) until no acid left in the organic layer. It was then dried by Na2SO4 and concentrated in vacuuo, which (Ig) was ready for the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,19842-08-1, its application will become more common.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAK, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (905 pag.)WO2017/35353; (2017); 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. 7477-10-3, name is 6-Chloro-5-nitronicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C6H3ClN2O4

[00190] To a stirred solution of 6-chloro-5-nitro-pyridine-3-carboxylic acid (500 mg, 2.46 mmol) in dioxane (5 mL) was added tert-butyl N-[(E)-4-aminobut- 2-enyl]carbamate hydrochloride (500 mg, 2.71 mmol) followed by DIPEA (1.09 mL, 6.27 mmol); mixture was stirred at RT overnight. The mixture was diluted with water and acidified to pH ~3 with 3 N HCI. The resulting suspension was filtered to give the desired product as a yellow solid, dried in oven (636 mg, 73%). 1H NMR (de-DMSO) d 13.20 (brs, 1H), 9.00 (t, J = 6 Hz, 1H), 8.89 (d, J = 4 Hz, 1H), 8.74 (d, J = 4 Hz, 1H), 6.99-6.91 (m, 1H), 5.72-5.53 (m, 2H), 4.27- 4.18 (m, 2H), 3.56-3.47 (m, 2H), 1.36 (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, 7477-10-3, 6-Chloro-5-nitronicotinic acid.

Reference:
Patent; TRILLIUM THERAPEUTICS INC.; SLASSI, Abdelmalik; DOVE, Peter; ROSA, David Alexander; WANG, Zezhou; WINSTON, Jeffrey Todd; LIN, Hoi Ying; (0 pag.)WO2020/10451; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 132097-09-7, 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.132097-09-7, name is 2,4-Dichloro-3-methylpyridine, molecular formula is C6H5Cl2N, molecular weight is 162.02, as common compound, the synthetic route is as follows.

4-HYDROXY-PIPERIDINE-1-CARBOXYLIC acid isopropyl ester (0.496 mL, 2. 90 mmol) was dissolved in anhydrous DIMETHYLACETAMIDE (DMA, 5 mL), NaH (60% oil dispersion, 116 mg, 2.90 mmol) was added and this mixture was stirred at 23C for 45 min, then this mixture was added dropwise to 2,4- dichloro-3-methyl-pyridine, which was dissolved in anhydrous DMA (4 mL). This mixture was stirred at 23 OC for 2 h then heated at 50C for 15 h, after which time the mixture was diluted with ET20 (140 mL), washed with water (14 mL), then brine twice (2 x 14 mL). The organic layer was separated, dried with MGS04, and the solvent was evaporated in vacuo to give an oil which was purified by flash chromatography using hexanes-EtOAc, 75: 25, V/V, then hexanes-EtOAc, 50: 50, V/V, to give 4-(2-chloro-3-methyl-pyridin-4-yloxy)-piperidine-1-carboxylic acid isopropyl ester as a solid (223 mg, 27%). H NMR (CDC13, 400 MHz) No. 8.09 (d, 1H), 6.69 (d, 1H), 4.91 (M, 1H), 4. 60 (M, 1H), 3.61 (M, 2H), 3.52 (M, 2H), 2.24 (s, 3H), 1.91 (M, 2H), 1.80 (M, 2H), 1.24 d, 6H). LRMS calculated for C15H21CIN203 : 312.12, Found: (MH) + 313. 4.

The chemical industry reduces the impact on the environment during synthesis 132097-09-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2005/7647; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 197376-47-9, 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 197376-47-9, name is Ethyl 6-Chloropyridine-3-acetate. This compound has unique chemical properties. The synthetic route is as follows.

[6′-(4-{[2-(Trifluoromethyl’)phenyl]oxy}-l-piperidinyl)-2,3′-bipyridin-5-yl]acetic acid Step 1 : 6 ‘-(4- ( r2-(Trifluoromethyl)phenyl1oxyl – 1 -piperidinvO-2.3 ‘-bipyridin-5-yll acetic acid Ethyl (6-chloro-pyridin-3-yl)-acetate (1.5 eq) was treated with a mixture of 5- (4,4,5, 5-tetramethyl-l,3,2-dioxaborolan-2-yl)-2-{4-[2-(trifluoromethyl)phenoxy]piperidin-l- yl}pyridine (from step 3 of example 1), Pd(OAc)2 (0.017 equiv.), Ph3P (0.05 equiv.), and 2M Na2CO3 (4.5 equiv.), and the mixture was heated at 80 0C. After a period of 4 h, the reaction mixture was hydro lyzed with 2M aqueous LiOH (5 eq) for 3 h at 22 C. The solution was neutralized with the addition of formic acid (30 eq) and concentrated. The residue was suspended in DMSO (0.04 M) and centrifuged. The supernatant was purified by reverse phase HPLC using a C18 CombiPrep ODS-AM column (gradient: 60% H2O in CH3CN to 5% H2O in CH3CN over 8 min) to obtain the title compound. MS: m/z 458.5 (ESI+)

According to the analysis of related databases, 197376-47-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK FROSST CANADA LTD.; WO2008/46226; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 851484-95-2, 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. 851484-95-2, name is 2-Chloro-5-fluoronicotinaldehyde, molecular formula is C6H3ClFNO, 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.

2-chloro-5-fluoronicotinaldehyde (20 g, 125 mmol) was taken up in THF (150 ml) at 0 C. (R)-2-Methylpropane-2-sulfinamide (16.71 g, 138 mmol) was added followed by dropvvise addition of iitaniumtetraethanolaie (22.88 ml, 150 mmol). The reaction mixture was stirred while warming to RT. After 3 hours the reaction mixture was cooled to 0 C, and 150ml of brine was added and stirred for 20 minutes. The mixture was filtered through Celite. The aqueous layer was separated and discarded. The organic layer with dried over Na2S04 and the solvent was removed to give (S,Z)-N-((2-chloro-5-fluoropyridm-3-yl)memylene)-2-methylpropane-2-sul.finaiTiide (32 g, 122 mmol, 97 % yield), which was carried on without further purification. LCMS: 263 M+H.

According to the analysis of related databases, 851484-95-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; WENGLOWSKY, Steven, Mark; BROOIJMANS, Natasja; MIDUTURU, Chandrasekhar, V.; BIFULCO, Neil; (206 pag.)WO2017/35354; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 122475-57-4, 4-Amino-2,3-dimethylpyridine, 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, Computed Properties of C7H10N2, blongs to pyridine-derivatives compound. Computed Properties of C7H10N2

To a solution of diphosgene (182 mg; 0.90 mmol) in THF (4 mL) was added dropwise a solution of 4- amino-2,3-dimethylpyridine (187 mg; 1.50 mmol), DMAP (19 mg; 0.15 mmol) and TEA (0.43 mL; 3.00 mmol) in THF (4mL) at 0 C. The mixture was allowed to warm up to rt and stirred for 2 h. The mixture was then treated with a solution of 4-[(4-chloro-2-fluoro-phenyl)methylene]piperidine, hydrochloride (390 mg; 1.50 mmol) and TEA (0.43 mL; 3.00 mmol) in THF (4 mL). After stirring for 16 h, the mixture was concentrated to dryness. The residue was purified by preparative HPLC to afford 4-[(4-chloro-2- fluoro-phenyl)methylene] -A-(2,3 -dimethyl-4-pyridyl)piperidine- 1 -carboxamide, trifluoroacetic acid (120 mg) as a yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,122475-57-4, 4-Amino-2,3-dimethylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; BASILEA PHARMACEUTICA INTERNATIONAL AG; RICHALET, Florian; EL SHEMERLY, Mahmoud; LANE, Heidi; (43 pag.)WO2019/115709; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1207625-29-3, 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. 1207625-29-3, name is 5-Bromo-6-fluoro-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H4BrFN2, 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.

Into a 250-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of the commercially available 5-bromo-6-fluoro- 1H-pyrrolo[2,3-bjpyridine (CAS, 1190321-99-3, 15 g, 69.76 mmol, 1.00 equiv) in N,Ndimethylformamide (150 mL). This was followed by the addition of sodium hydride (4.2 g, 175.00 mmol, 1.50 equiv), in portions at 0 degree. After 0.5 h stirring, to this was added SEM-Cl (14 g, 84.34 mmol, 1.20 equiv) dropwise with stirring at 0 degree. The resulting solution was allowed to react, with stirring, for an additional 3 h at room temperature. The reaction was then quenched by the addition of 300 mL of water. The resulting solution was extracted with 3×200 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 3×200 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (0:1-1:10). This resulted in 15 g (62%) of 5-bromo-6-fluoro-1-[[2- (trimethylsilyl)ethoxyj methylj -1 H-pyrrolo [2,3 -bjpyridine as yellow oil. H-NMR (CDC13, 300 MHz) 6: 8.19 (d, J=8.7 Hz, 1H), 7.37 (d, J=3.6 Hz, 1H), 6.54 (d, J=3.6 Hz, 1H), 5.64 (s, 2H), 3.58 (t, J=8.1 Hz, 2H), 0.98-0.93 (t, J=8.1 Hz, 2H), 0.00 (s, 9H).

According to the analysis of related databases, 1207625-29-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NEWAVE PHARMACEUTICAL INC.; CHEN, Yi; LOU, Yan; (108 pag.)WO2019/40550; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem