Tag: M.W:200-300

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. 65-22-5, name is 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde hydrochloride, molecular formula is C8H10ClNO3, 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 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde hydrochloride

To a solution of 0.25 mmol (0.036 g) triethylenetetramine in10 mL methanol, 0.5 mmol (0.1 g) of pyridoxal chloridrate and1.3 mmol (136 mL) triethylamine were added. The solution was heated in an oil-bath at 55 C and stirred by 15 min. Then a solution of 0.25 mmol (0.091 g) of Ni(ClO4)26H2O in 5 mL methanol was dropped to the main solution, which was stirred at 55 C by 1 h. The slow evaporation of the solvent afforded orange crystals after 4days. A similar one-pot synthesis was already reported [13].Yield: 65%. Melting point: 118e119 C. Anal. Calc: C22H34N6O6Ni:C, 49.19; H, 6.33; N,15.65. Found: C, 49.12, H, 6.39; N,15.44%. IR (KBrpellets, cm1): 3526 [m, n(OeH)alcohols]; 3302 [m, n(OeH)alcohol];2921 [w, n(CeH)sp3)]; 1637 [s, n(C]N)]; 1312 [m, n(OeH)alcohol]1263 [m, n(CeO)phenol.]; 1201[s, n(CleO)percholate]; 1012 [s,n(CeO)alcohols].

With the rapid development of chemical substances, we look forward to future research findings about 65-22-5.

Reference:
Article; Back, Davi Fernando; De Oliveira, Gelson Manzoni; Fontana, Liniquer Andre; Ramao, Brenda Fiorin; Roman, Daiane; Iglesias, Bernardo Almeida; Journal of Molecular Structure; vol. 1100; (2015); p. 264 – 271;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 153034-86-7 ,Some common heterocyclic compound, 153034-86-7, molecular formula is C5H3ClIN, 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.

Step 1 To a solution of 2-cyclopentenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (681 mg, 3.51 mmol) and 2-chloro-4-iodopyridine (700 mg, 2.92 mmol) in 1,4-dioxane (12 mL) was added 2.0 M aqueous Na2CO3 (4.39 mL, 8.77 mmol) and tetrakis(triphenylphosphine)palladium(0) (67.6 mg, 0.059 mmol). The reaction mixture was heated at 90 C. for 3.5 h then cooled to room temperature, diluted with water and extracted with EtOAc (2*). The combined organics were dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography (0% to 10% EtOAc/hexanes) to afford 450 mg (86%) of 2-chloro-4-cyclopent-1-enyl-pyridine as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,153034-86-7, its application will become more common.

Reference:
Patent; Hendricks, Robert Than; Hermann, Johannes; Kondru, Rama; Lou, Yan; Lynch, Stephen M.; Owens, Timothy D.; Soth, Michael; US2011/230462; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1032943-41-1, 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. 1032943-41-1, name is 4-Bromo-1-methyl-1H-pyrazolo[3,4-c]pyridine, molecular formula is C7H6BrN3, 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 3 (GP 3): Suzuki coupling (Conditions A); The heteroaryl halide (1 eq), the respective aryl pinacolato boronate or aryl boronic acid (1.2 to 1.5 eq.) and Pd(PPh3)4 (6 mol%) were weighed into a Biotage microwave vial and capped. Toluene (6 mL per mmol halide), EtOH (6 mL per mmol halide) and 1M aq. Na2CO3 solution (2 eq.) were added by syringe. The resulting mixture was prestirred (10 sec) and subsequently heated to 120 C for 15 min (fixed hold time) in a Biotage Initiator microwave reactor. The reaction mixture was diluted with water and ethyl acetate, the layers were separated and the aqueous layer extracted with ethyl acetate. The combined organic layers were dried and concentrated in vacuo. The residue was optionally purified by flash column chromatography and/or trituration and/or preparative HPLC.; Intermediate 3.1; Preparation of 4-(1-Methyl-1 H-pyrazolo[3,4-c]pyridin-4-yl)-phenylamine; [Show Image] In analogy to GP 3, 1.06 g of Intermediate 2.1 (5 mmol, 1 eq.), 1.31 g of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (6 mmol, 1.2 eq.) and 347 mg Pd(PPh3)4 (6 mol%) were weighed into a Biotage microwave vial and capped. 30 mL toluene, 30 mL EtOH and 1M aq. Na2CO3 solution (9.65 mL, 1.9 eq.) were subsequently added by syringe. The resulting mixture was prestirred (10 sec) and subsequently heated to 120 C for 15 min (fixed hold time) in a Biotage Initiator(at) microwave reactor. The reaction mixture was diluted with water and ethyl acetate, the layers were separated and the aqueous layer extracted with ethyl acetate. The combined organic layers were dried and concentrated in vacuo to yield after trituration 701 mg of the desired product (3.13 mmol, 63% yield), which was used for subsequent transformations without further purification. 1H-NMR (d6-DMSO; 400 MHz): 8.97 (s, 1 H); 8.24 – 8.25 (m, 2 H); 7.46 (d, 2 H); 6.69 (d, 2 H); 5.40 (br. s, 2 H); 4.15 (s, 3 H).

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 1032943-41-1, 4-Bromo-1-methyl-1H-pyrazolo[3,4-c]pyridine.

Reference:
Patent; Bayer Schering Pharma Aktiengesellschaft; EP1932845; (2008); 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. 67443-38-3, name is 5-Bromo-2-chloro-3-nitropyridine, the common compound, a new synthetic route is introduced below. Recommanded Product: 5-Bromo-2-chloro-3-nitropyridine

To a suspension of sodium hydride (5.31 g, 133 mmol) in 1 ,4-dioxane (250 ml), ethyl glycolate (12.56 ml, 133 mmol) was added drop wise over a period of 30 minutes ensuring that the temperature was maintained below 30C. The resulting thick suspension was stirred at room temperature for 15 minutes. In a separate 11 round- bottomed flask was added 5-bromo-2-chloro-3-nitropyridine (21 g, 88 mmol) in 1 ,4- dioxane (150 ml) to give a brown solution. The suspension of sodium hydride and ethyl glycolate was added drop wise over a period of 30 minutes at 0C. The resulting reaction mixture was heated to 80C overnight. The reaction mixture was concentrated under reduced pressure and the crude residue was purified by Biotage silica chromatography (gradient 0% to 10% ethyl acetate in n- hexanes) to give the title compound (1 .8g, 44%). N R (500 MHz, CDCI3): 8.48 (1 H, s), 8.42 (1 H, s), 5.07 (2H, s), 4.28-4.24 (2H, q), 1.31-1.28 (3H, t).

The synthetic route of 67443-38-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMAC DISCOVERY LIMITED; ZHANG, Lixin; TREVITT, Graham, Peter; MIEL, Hughes; BURKAMP, Frank; HARRISON, Timothy; WILKINSON, Andrew, John; FABRITIUS, Charles-Henry; WO2011/77098; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 116026-94-9 ,Some common heterocyclic compound, 116026-94-9, molecular formula is C11H14N2O3, 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 mixture of the aldehyde (0.222 g, 1 mmol) and DMF (3 mL) was added MeI (0.178 g, 1.25 mmol) at 0 0C. NaH (0.052 g, 60% mineral oil, 1.35 mmol) was added in three portions over 15 min and the resulting yellowish suspension was stirred for an additional 60 min. The mixture was warmed to rt and quenched by the addition Of NaHCO3 (10 mL) and H2O (10 mL). The mixture was extracted with Et2O (3><1 OmL), and the combined organic layers were washed with H2O (10 mL), NaHCO3 (10 mL), brine (10 mL), and dried over Na2SO4. The product was further purified by flash chromatography (25% EtOAc in hexanes) to afford an oil (0.197 g, 84%), which was used in the next step

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. 116026-94-9, tert-Butyl (3-formylpyridin-2-yl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LAUTENS, Mark; YUEN, Josephine; FANG, Yuanqing; WO2008/22467; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 153034-90-3, 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. 153034-90-3, name is 2-Chloro-4-iodonicotinaldehyde, molecular formula is C6H3ClINO, 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.

According to GP1, 2-chloro-4-iodonicotinaldehyde (989 mg, 3.70 mmol), CsF (112 mg, 0.74 mmol), and t-BuMe2SiCN (784 mg, 5.60mmol) were dissolved in anhyd MeCN (3.7 mL). The reaction mixture was stirred at 25 C for 12 h. The resulting mixture was diluted with H2O (20 mL) and extracted with EtOAc (3 × 40 mL). The combined organic phases were dried (anhyd MgSO4), filtered, and the solvents were evaporated in vacuo. The crude product was purified by flash column chromatography on silica gel (i-hexane/EtOAc, 9:1 + Et3N 2%) yielding 2-(tert-butyldimethylsilyloxy)-2-(2-chloro-4-iodopyridin-3-yl)acetonitrile as a light yellow solid (1.5 g, 98%); mp 83.4-85.2 C.IR (Diamond-ATR, neat): 2955, 2859, 1636, 1548, 1472, 1337, 1302,1255, 1186, 1066, 939, 833, 781 cm-1.1H NMR (400 MHz, CDCl3): delta = 7.99 (d, J = 5.2 Hz, 1 H), 7.85 (d, J = 5.2Hz, 1 H), 6.24 (s, 1 H), 0.94 (s, 9 H), 0.31 (s, 3 H), 0.13 (s, 3 H).13C NMR (101 MHz, CDCl3): delta = 150.3, 149.9, 135.5, 132.5, 116.7,110.3, 65.2, 25.4, 18.0, -4.9, -5.1.MS (70 eV, EI): m/z (%) = 353 (28), 351 (79), 323 (52), 296 (4), 226(35), 224 (100), 209 (12), 150 (6).HRMS (EI): m/z [M – C4H9]+ calcd for C9H9ClIN2OSi: 350.9217; found:350.9210.

According to the analysis of related databases, 153034-90-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Castello-Mico, Alicia; Knochel, Paul; Synthesis; vol. 50; 1; (2018); p. 155 – 169;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 55304-75-1, 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 55304-75-1, name is 2,6-Dichloro-3-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A DMF/water solution (1:1, 2 mL per 1 mmol of 1) of K3PO4 (1.5 mmol), Pd(OAc)2(2 mol %), and arylboronic acid 2 (2.2 mmol) was stirred at room temperaturefor 8-12 h (tlc control). After completion of the reaction, the mixture wasextracted with CH2Cl2 and the combined organic layers were dried (Na2SO4), filtered and the filtrate was concentrated in vacuo. The residue was purified bycolumn chromatography (silica gel, EtOAc/heptane = 1:4). Starting with 1(216 mg, 1.0 mmol), K3PO4 (345 mg, 2.5 mmol), Pd(OAc)2 (2 mol %), arylboronic acid (334 mg, 2.20 mmol), and solution of DMF andwater (1:1) (2 mL), 4a-f was isolated as a yield.

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 55304-75-1, 2,6-Dichloro-3-(trifluoromethyl)pyridine.

Reference:
Article; Ahmed, Shahzad; Sharif, Muhammad; Shoaib, Khurram; Reimann, Sebastian; Iqbal, Jamshed; Patonay, Tamas; Spannenberg, Anke; Langer, Peter; Tetrahedron Letters; vol. 54; 13; (2013); p. 1669 – 1672;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1010120-55-4, 5-Bromo[1,2,4]triazolo[1,5-a]pyridin-2-amine, 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, COA of Formula: C6H5BrN4, blongs to pyridine-derivatives compound. COA of Formula: C6H5BrN4

3-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine (purchased from Mesh Mall) 30.00 g (0.14 mol) was added to a 1L three-necked bottle,4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-benzyl) is added thereto in this orderThiomorpholine 1,1-dioxide 58.50 g (0.15 mol), dioxane 400 ml, potassium carbonate 58.60 g (0.42 mol), water 100 ml, Pd(dppf)Cl2 5.78 g (0.007 mol).Under argon protection, the mixture was warmed to 90 C and the reaction was stirred for 16 h.After the reaction is completed, cool to room temperature, add 400 ml of dichloromethane, then wash twice with water, 800 ml each time, and concentrate the organic layer to dryness.The residue was purified by column chromatography (eluent: dichloromethane:methanol = 100:1) to give the title product as a pale yellow solid, 27.2 g, 54% yield, purity 96%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1010120-55-4, 5-Bromo[1,2,4]triazolo[1,5-a]pyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; China Pharmaceutical Research And Development Center Co., Ltd.; Yin Huijun; Yan Xu; Zong Libin; Dong Liuxin; Han Yachao; Xi Qingchuan; Dou Haoshuai; Mi Zhen; Yang Yan; (30 pag.)CN107880038; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 882521-63-3, 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 882521-63-3 as follows.

General procedure: To a microwave tube was added [1,2,4]triazolo[1,5-a]pyridin-2-amine 13 (1 equiv), K2CO3 (2.0 equiv), Pd(PPh3)4 (0.056 equiv), and the corresponding boronic acid (1.5 equiv). 5 mL of EtOH:H2O (1:1) was used as solvent, and the microwave conditions employed were 150 C for 30 min. After solvent evaporation, the product was purified by flash chromatography on silica gel using as eluent a gradient of EtOAC (0 – 100%) in n-hexane or MeOH (0 – 10%) in DCM to afford the desired compound 16 (adapted from 4).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,882521-63-3, its application will become more common.

Reference:
Article; Ribeiro, Carlos J.A.; Kankanala, Jayakanth; Xie, Jiashu; Williams, Jessica; Aihara, Hideki; Wang, Zhengqiang; Bioorganic and Medicinal Chemistry Letters; vol. 29; 2; (2019); p. 257 – 261;,
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.942947-94-6, name is 5-Bromo-4-chloropyridin-2-amine, molecular formula is C5H4BrClN2, molecular weight is 207.4557, as common compound, the synthetic route is as follows.Product Details of 942947-94-6

To a 1 L 3 necked round-bottomed flask equipped with a magnetic stirrer, heating mantle, and N2 inlet was added 5-bromo-4-chloropyridin-2 -amine (25 g, 121 mmol) and sodium hydrogen sulfide hydrate (26.5 g, 362 mmol). The flask was evacuated and purged with N2 three times. To the solids, N2 sparged l-methyl-2-pyrrolidinone (250 mL) was added. The green suspension was heated to 70 C for 17 hours. The suspension was cooled to room temperature. A cooled bleach scrubber containing 750 mL of bleach was installed and to the suspension concentrated HCl (24.90 mL, 301 mmol) was added. Gas evolution was noted. The resulting dark brown/red suspension was sparged with N2 for 30 minutes. The solids were removed under N2 filtration and were washed with N2 sparged ethanol (100 mL) to give a solution of 2-amino-5-bromopyridine-4-thiol (350 mL) which was used directly in the next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,942947-94-6, 5-Bromo-4-chloropyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; ABBVIE INC.; KALLEMEYN, Jeff M.; KU, Yi-Yin; MULHERN, Mathew M.; WO2015/157360; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem