Tag: M.W:100-200

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. 1122-43-6, name is 2,6-Dimethyl-3-hydroxypyridine, the common compound, a new synthetic route is introduced below. Quality Control of 2,6-Dimethyl-3-hydroxypyridine

Example 150 5-[3-(2,4-Bis-trifluoromethyl-phenyl)-6-methyl-pyridin-2-ylmethyl]-2-(2,3-difluoro-phenyl)-5H-imidazo[4,5-d]pyridazine (Compound 336) 2,6-Dimethyl-pyridin-3-ol (1 g) was dissolved in pyridine (20 mL) and triflic anhydride (1.5 mL) was added. After 3 hr of stirring the reaction was evaporated and chromatographed to give quantitatively trifluoro-methanesulfonic acid 2,6-dimethyl-pyridin-3-yl ester.

The synthetic route of 1122-43-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Genelabs Technologies, Inc.; US2009/226398; (2009); 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. 131747-55-2, name is 2-Fluoro-3-(hydroxymethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C6H6FNO

Example 100: 3-(4-Chlorophenylsulfonylmethyl)-2-fluoropyridine A chloroform (10 ml) solution of (2-fluoropyridin-3-yl)methanol (49 mg, 0.385 mmol) and thionyl chloride (0.14 ml, 1.93 mmol) was stirred at 50C for 3.5 hours.. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure.. The residue thus obtained was dissolved in butanol (5 ml), followed by the addition of sodium 4-chlorobenzenesulfinate (92 mg, 0.462 mmol) and potassium acetate (76 mg, 0.770 mmol).. The mixture was stirred at 70 to 80C for 12 hours.. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure.. ethyl acetate was added to the residue, and the mixture was washed successively with a saturated aqueous solution of sodium bicarbonate and brine, and then, dried over anhydrous sodium sulfate.. After filtration, the filtrate was concentrated under reduced pressure.. The residue was subjected to flash chromatography on a silica gel column.. The fraction obtained from the hexane:ethyl acetate (=2:1) elude was concentrated under reduced pressure, whereby the title compound (59 mg, 54%) was obtained as a white solid. IR (ATR) nu: 3097, 2989, 2933, 1643, 1606, 1573, 1469, 1434, 1409, 1392, 1321, 1276, 1240, 1184, 1170, 1149, 1083, 1010, 956, 902, 842, 813, 779, 763, 725, 696, 640, 582, 541, 522, 480, 445 cm-1.1H-NMR (400MHz, CDCl3) delta: 4.38(2H,s), 7.21-7.30(1H,m), 7.47(2H,d,J=8.8Hz), 7.61(2H,d,J=8.8Hz), 7.87-7.94(1H,m), 8.19-8.25(1H,m). MS (m/z): 286 (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, 131747-55-2, 2-Fluoro-3-(hydroxymethyl)pyridine.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1466898; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 3678-62-4 ,Some common heterocyclic compound, 3678-62-4, molecular formula is C6H6ClN, 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.

10 g of 2-chloro-4-methylpyridine are dissolved in 30 ml of CH3CN and a mixture of AIBN (3 g) and NCS (30 g) is added. The resulting mixture is refluxed for 4 hours. After removing the solvent, the crude product is further purified by distillation (boiling point: 70 C., 20 mtorr)

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. 3678-62-4, 2-Chloro-4-methylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AVENTIS PHARMA S.A.; US2004/248884; (2004); 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. 112110-07-3, name is 5-(Trifluoromethyl)pyridin-3-amine, molecular formula is C6H5F3N2, 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. Safety of 5-(Trifluoromethyl)pyridin-3-amine

To a mixture of 2-(4-bromo-2,5-difluoro-phenyl)acetic acid (9, 2.16 g, 8.60 mmol), 5-(trifluoromethyl)pyridin-3-amine (10, 1.39 g, 8.57 mmol) and pyridine (2.09 ml, 25.8 mmol) in ethyl acetate (85 ml) was added slowly propylphosphonic anhydride (50 wt % solution in ethyl acetate, 10.1 ml, 17.2 mmol). The reaction mixture was allowed to stir at room temperature for 3 hours. The reaction was diluted with ethyl acetate and was washed with saturated aqueous ammonium chloride, water and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to provide 3.29 g (97% yield) of compound 11 that was used in the next step without further purification. MS ESI [M+H+]+=397.05.

With the rapid development of chemical substances, we look forward to future research findings about 112110-07-3.

Reference:
Patent; Plexxikon Inc.; Lin, Jack; Ibrahim, Prabha N.; Albers, Aaron; Buell, John; Guo, Zuojun; Pham, Phuongly; Powers, Hannah; Shi, Songyuan; Spevak, Wayne; Wu, Guoxian; Zhang, Jiazhong; Zhang, Ying; (132 pag.)US2017/267660; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 87674-21-3, 1-(3-Fluoropyridin-4-yl)ethanone, 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 C7H6FNO, blongs to pyridine-derivatives compound. Computed Properties of C7H6FNO

To a stirred solution of 3-fluoro-4-acetylpyridine (5.3 g, 38.1 mmol) in glacial acetic acid (14 mL) and 48% hydrobromic acid (5.3 mL), bromine (2 mL, 38 mmol) in glacial acetic acid (5.3 mL) was added slowly and dropwise. After addition, the solution was stirred at 60 C. for 2.5 h then it was cooled down and ethylacetate (70 mL) was added. After 30′ stirring the mixture was filtered and the solid was washed thoroughly with ethylacetate and dried. The title compound was obtained in 82% yield (9.4 g). 1H NMR (DMSO-d6/400 MHz) delta ppm 4.88 (s, 2 H) 7.83 (dd, 1 H) 8.62 (dd, 1 H) 8.81 (d, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,87674-21-3, 1-(3-Fluoropyridin-4-yl)ethanone, and friends who are interested can also refer to it.

Reference:
Patent; Pharmacia Italia S.p.A.; US2007/142414; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1019021-85-2, 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.1019021-85-2, name is 6-Fluoroimidazo[1,2-a]pyridine-3-carboxylic acid, molecular formula is C8H5FN2O2, molecular weight is 180.1359, as common compound, the synthetic route is as follows.

Oxalyl chloride (10 mL, 1 10 mmol) was added dropwise to a stirred suspension of 6- fluoroimidazo[1 ,2-a]pyridine-3-carboxylic acid (24b) (2 g, 1 1 mmol) and catalytic amounts of DMF in dichloromethane (20 mL). After 5 hours, the solvent was evaporated and the solid was suspended in dry DCE (20 mL) and added to a stirred solution of 3- amino-4-methylbenzonitrile (1 .45 g, 1 1 mmol) and DIEA (6 mmol) in DCE (1 0 mL) at 0 C. After the addition, the reaction was heated at 60 C for 5 hours. The mixture was subjected to standard aqueous work and silica purification to give N-(5-cyano-2- methylphenyl)-6-fluoroimidazo[1 ,2-a]pyridine-3-carboxamide (39) as a solid. 1 H NMR (400MHz, c/6-DMSO) delta 10.14 (s, 1 H), 9.45 (dd, J = 5.2, 2.0 Hz, 1 H), 8.62 (s, 1 H), 7.90 – 7.87 (m, 2 H), 7.68-7.63 (m, 1 H), 7.53 (d, J = 8.0 Hz, 1 H), 2.37 (s, 3H). MS m/z 295.1 (M+1 ) +. NH2OH (5 mL, 16.1 mmol) was added in one portion to a stirred suspension of N-(5- cyano-2-methylphenyl)-6-fluoroimidazo[1 ,2-a]pyridine-3-carboxamide (39) (0.95 g, 3.23 mmol). The resulting suspension was heated at 60 C overnight and then cooled to 0 C. The product, (Z)-6-fluoro-N-(5-(N’-hydroxycarbamimidoyl)-2-methylphenyl)imidazo[1 ,2- a]pyridine-3-carboxamide (40) was collected by filtration. MS m/z 328.1 (M+1 ) +.

Statistics shows that 1019021-85-2 is playing an increasingly important role. we look forward to future research findings about 6-Fluoroimidazo[1,2-a]pyridine-3-carboxylic acid.

Reference:
Patent; IRM LLC; LIU, Xiaodong; LI, Xiaolin; LOREN, Jon; MOLTENI, Valentina; NABAKKA, Juliet; NGUYEN, Bao; PETRASSI, Hank Michael James; YEH, Vince; WO2013/33116; (2013); 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. 1122-43-6, name is 2,6-Dimethyl-3-hydroxypyridine, the common compound, a new synthetic route is introduced below. name: 2,6-Dimethyl-3-hydroxypyridine

Example 66; (3R)-1-{2-[(2,6-Dimethylpyridin-3-yl)oxy]ethyl}-3-{[2-piperidin-1-yl-2-(2-thienyl)propanoyl]oxy}-1-azoniabicyclo[2.2.2]octane bromide (Isomer 1); a) 3-(2-Bromoethoxy)-2,6-dimethylpyridine; 2,6-Dimethylpyridin-3-ol (2 g) in dry DMF (20 mL) under nitrogen was treated with sodium hydride (1.234 g). After the initial effervescence ceased 1,2-dibromoethane (6.10 g) was added in one portion causing an exotherm to 40 C. The mixture was stirred at room temperature overnight, diluted with water (100 mL), and the products extracted into ether (3×75 mL). The dried extracts were concentrated to dryness, and the residue purified on silica gel eluting with ether/dichloromethane (1:1). The subtitled compound was isolated as an oil (1.2 g).1H NMR (400 MHz, CDCl3) delta 6.98 (1H, d), 6.92 (1H, d), 4.26 (2H, t), 3.65 (2H, t), 2.47 (6H, d).

The synthetic route of 1122-43-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ford, Rhonan; Mete, Antonio; Millichip, Ian; Teobald, Barry; US2010/113510; (2010); 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

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

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