Month: April 2022

Adding a certain compound to certain chemical reactions, such as: 59290-81-2, 2-Methyl-5-nitro-3-pyridinecarboxylic acid, 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, 59290-81-2, blongs to pyridine-derivatives compound. Safety of 2-Methyl-5-nitro-3-pyridinecarboxylic acid

Step 1: Synthesis ofZ-1aED-1 a (15.6 g, 85.7 mmol) is placed in ie/f.-BuOH (300 mL), combined with DPPA (27 mL, 125 mmol) and NMM (12 mL, 108 mmol) and refluxed for 5 h. After cooling, saturated sodium chloride solution is added and the mixture is extracted several times with EA. The combined organic phases are washed with saturated sodium chloride solution, dried on MgS04, filtered and evaporated down using the rotary evaporator. The residue is taken up in water and freeze-dried. The resulting Z-1 a (HPLC-MS: tRet. = 1 .73 min; MS (M+H)+ = 254) is used without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,59290-81-2, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ETTMAYER, Peter; STEURER, Steffen; WO2011/117382; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 135124-71-9 ,Some common heterocyclic compound, 135124-71-9, molecular formula is C7H6N2O, 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.

d) 5-Cyano-pyridine-3-carbaldehyde A black suspension of (5-cyano-pyridin-3-yl)-methanol (0.070 g, 0.52 mmol), anhydrous CH2Cl2 (1.04 mL) and manganese oxide (0.181 g, 2.09 mmol) was heated to reflux and monitored by TLC. After 8 h, the reaction mixture was cooled to room temperature and additional manganese oxide (0.095 g, 1.1 mmol) was added to the reaction flask. The reaction mixture was then heated to reflux. After 18 h, the reaction was still not complete by TLC and additional manganese oxide (0.097 g, 1.1 mmol) was added to the reaction flask. After heating at 60 C. for 72 h, the reaction mixture was cooled to room temperature, diluted with EtOAc (50 mL), passed through celite and washed with additional EtOAc (50 mL). The organic filtrate was dried over MgSO4, filtered through sintered glass and concentrated to yield 0.064 g (93%) of a white solid. It was purified by column chromatography (elution with EtOAC:hexanes, 1:3) and yielded 0.038 g (55%) of the title compound as a white solid. 1H NMR (CDCl3): 10.17 (s, 1H), 9.28 (d, J=1.9 Hz, 1H), 9.11 (d, J=2.2 Hz, 1H), 8.45 (dd, J=2.2, 1.9 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,135124-71-9, its application will become more common.

Reference:
Patent; Cytovia, Inc.; US2006/104998; (2006); 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. 55404-31-4, name is 3-Bromo-2-chloro-4-methylpyridine, the common compound, a new synthetic route is introduced below. Formula: C6H5BrClN

Example 1; Synthesis of 3-(2-amino-6-quinazolinyl)-1 -(3-chlorophenyl)-4-methyl-2(1 H)- pyridinone; Step 1 : 2-(4-methoxybenzyloxy)-3-bromo-4-methyl; Pyridine To a mixture of 60% NaH in mineral oil (0.290 g, 7.27 mmol) in THF (15 ml_) at RT in a resealable pressure vessel was added (4-methoxyphenyl)methanol (0.906 ml, 7.27 mmol). After 5 minutes, 3-bromo-2-chloro-4-picoline (1.00 g, 4.84 mmol) was added and the mixture was heated to 75 0C. After 1 hr, water was added and the mixture was diluted with EtOAc. After washing with water and brine, the organic fraction was dried with sodium sulfate and purified by silica gel chromatography using 0-30% EtOAalphahexanes to afford 2-(4-methoxybenzyloxy)- 3-bromo-4-methylpyridine as a colorless oil. M+H+ = 308.0.

The synthetic route of 55404-31-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; WO2008/11109; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 189230-41-9, 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 189230-41-9 as follows.

[0355] Reference AD [0356] Synthesis of 5-chloro-N-cyclopropyl-3-(4-(2-fluoro-4-methoxyphenoxy)piperidin-l- yl)pyrido[3,4-b]pyrazin-2-amine [0358] [0359] Step 1 : 5-bromopyrido[3,4-b]pyrazine-2,3(lH,4H)-dione [0360] A solution of l,2-di(lH-imidazol-l-yl)ethane-l,2-dione (1.456 g, 7.66 mmol) and 2- bromopyridine-3,4-diamine (1.2 g, 6.38 mmol) in DMF (21.27 ml) was stirred at RT overnight. The precipitate was filtered and washed with anhydrous THF to give the title compound as a grey solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,189230-41-9, its application will become more common.

Reference:
Patent; ENVOY THERAPEUTICS, INC.; HITCHCOCK, Stephen; MONENSCHEIN, Holger; REICHARD, Holly; SUN, Huikai; KIKUCHI, Shota; MACKLIN, Todd; HOPKINS, Maria; WO2014/28479; (2014); 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. 122306-01-8, name is (6-Bromopyridin-3-yl)methanol, 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. COA of Formula: C6H6BrNO

To a mechanically-stirred solution of 78.12 g of thionyl chloride in 450 mL of acetonitrile at 15 C. was added a solution of 160.75 g of 3-hydroxymethyl-6-bromopyridine in 446 mL of acetonitrile over 30 minutes. The temperature rose to 22 C. during the addition, and the reaction mixture was stirred for 15 minutes at room temperature. The mixture was cooled in an ice bath, and a solution of 70 g of NaOH in 1.4 L of water was added at such a rate that the temperature did not exceed 15 C. 603 mL of toluene was added to the mixture and stirred rapidly. The layers were separated. The aqueous phase was reextracted with toluene. The combined organic phase was concentrated in vacuo to give 181.61 g of 3-chloromethyl-6-bromopyridine.

With the rapid development of chemical substances, we look forward to future research findings about 122306-01-8.

Reference:
Patent; G. D. Searle & Co.; US5420270; (1995); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 130473-26-6, 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 130473-26-6, name is 1H-Pyrrolo[2,3-c]pyridine-5-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

C174 (500 mg, 3.42 mmol) is dissolved in 1.5 mL formic acid. The solution is cooled to in an ice bath, 30% aqueous hydrogen peroxide (722 muL, 6.8 mmol) is added drop-wise, and the reaction is stirred 1 h in an ice bath, and allowed to stand overnight at 5 C. The mixture is diluted with water, the solid is collected, washed with water and is dried to give 522 mg of an off-white solid. The formate salt is added to 7 mL water, 3 mL 2N NaOH is added, and the pH is adjusted to 3 with 5% aqueous HCl. The precipitate is collected and is dried to afford 1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid (C176) (67% yield). HRMS (FAB) calculated for C8H6N2O2+H: 163.0508, found 163.0507 (M+H)+.

According to the analysis of related databases, 130473-26-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wishka, Donn G.; Reitz, Steven Charles; Piotrowski, David W.; Groppi JR., Vincent E.; US2003/45540; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 89364-04-5 ,Some common heterocyclic compound, 89364-04-5, molecular formula is C5H3BrN2O2, 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: 3-(4-bromophenyl)-4-nitropyridine To a stirred solution of 3-bromo-4-nitropyridine (100 g, 492.6 mmol), (4-bromophenyl)boronic acid (98.6 g, 492.6 mmol), and potassium carbonate (203.9 g, 1.47 mol) in toluene (1000 ml)-water (100 ml) was added tetrakis(triphenylphosphine)palladium (14.8 g, 12.8 mmol) at room temperature under nitrogen atmosphere; the mixture was degassed with nitrogen three times. The resulting mixture was stirred at 50 C. overnight. TLC showed the reaction was complete. The solid was removed through filtration and washed with ethyl acetate (100 ml*3). The organic layer was collected and the aqueous layer was extracted with ethyl acetate (100 ml*2). The combined organic layers were washed with brine (400 ml), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a crude residue which was purified by silica gel pad (eluted with 10-33% ethyl acetate in hexane) to afford 3-(4-bromophenyl)-4-nitropyridine (89 g, yield 65%) as yellow solid.

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. 89364-04-5, 3-Bromo-4-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Arvinas, Inc.; Crew, Andrew P.; Berlin, Michael; Flanagan, John J.; Dong, Hanqing; Ishchenko, Alexey; (559 pag.)US2018/125821; (2018); 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. 777931-67-6, name is 3-Bromo-2-chloro-6-methoxypyridine, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

Into a 100-mL vial maintained with an inert atmosphere of nitrogen, to a solution of 3-bromo-2-chloro-6-methoxypyridine (2.00 g, 8.900 mmol, 1.00 equiv.) in 1,4-dioxane (20 mL), added Pd(dppf)Cl2.CH2Cl2 (0.36 g, 0.450 mmol, 0.05 equiv.), Zn(CH3)2 (17 mL, 17.000 mmol, 2.00 equiv.). The resulting solution was stirred 16 h at 90 C. The mixture was concentrated under vacuum. The residue product was purified by chromatogram on silica gel with ethyl acetate/petroleum ether (2:98) to yield 2-(6-(1-ethyl-4-fluoro-1H-indazol-6-yl)-2-methoxypyridin-3-yl)-3-methylbutanal as yellow oil. Mass spectrum (ESI, m/z): Calculated for C7H8ClNO, 158.0 [M+H], found 157.8.

The synthetic route of 777931-67-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica NV; Zhang, Xuqing; Macielag, Mark J.; (179 pag.)US2019/47959; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 578007-66-6 , The common heterocyclic compound, 578007-66-6, name is 5-Bromo-3-iodo-2-methoxypyridine, molecular formula is C6H5BrINO, 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: tert-Butyl (1-(4-((5-bromo-2-methoxypyridin-3- yl)ethynyl)phenyl)cyclobutyl)carbamate: To a degassed solution of 5-bromo-3-iodo-2- methoxypyridine (823 mg, 2.62 mmol) in triethylamine (8.0 mL) at 0 C was added Pd(PfBu3)2 (1 10.4 mg, 6 mol%), Cul (5.0 mg, 1 mol%) and terf-butyl (1-(4- ethynylphenyl)cyclobutyl)carbamate (71 1 mg, 2.62 mmol). The brown suspension was stirred for 56 hours at room temperature before the reaction mixture was suspended in dichloromethane and washed with brine, dried over magnesium sulphate, filtered and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (gradient 10 to 25% EtOAc in hexane) to give the title compound as a white solid (1.04 g, 87%). H-NMR (500 MHz, CDCI3) delta 8.14 (d, 1 H), 7.84 (d, 1 H), 7.52 (dd, 2H), 7.41 (d, 2H), 5.13 (bs, 1 H), 4.01 (s, 3H), 2.50-2.56 (m, 4H), 2.09-2.14 (m, 1 H), 1.84-1.90 (m, 1 H), 1.36 (bs, 9H).

The synthetic route of 578007-66-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMAC DISCOVERY LIMITED; BELL, Mark, Peter; O’DOWD, Colin, Roderick; ROUNTREE, James, Samuel, Shane; TREVITT, Graham, Peter; HARRISON, Timothy; MCFARLAND, Mary, Melissa; WO2011/55115; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 33252-28-7, 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.33252-28-7, name is 6-Chloronicotinonitrile, molecular formula is C6H3ClN2, molecular weight is 138.55, as common compound, the synthetic route is as follows.

[N- (5-CYANO-2-PHENYL-LH-PYRROLOF2, 3-BLPYRIDIN-3-YL)-ACETAMIDE] [6-CHLORO-NICOTINONITRILE] (1.38 g, 10 mmol) was dissolved in 1,4-dioxane (50 ml). Hydrazine hydrate (0.525 ml, 10.4 mmol) was added and the resulting solution stirred for 1.5h, whereupon it was concentrated in vacuo. The residue was chromatographed (silica gel, gradient ethyl acetate/heptane from 1: 1 to 1: 0). The slower running component was concentrated in vacuo to afford the 6-hydrazino-nicotinonitrile monohydrate [0.80 g, 53%, APCI-MS m/z: 135.2 [MH+] ]. Part of this hydrazine (67 mg, 0.5 mmol) and [N- (2-OXO-2-] [PHENYL-ETHYL)-ACETAMIDE] (85 mg, 0.5 mmol) were fused together for lh at 230 [C.] The reaction mixture was allowed to cool and the glassy solid suspended in warm dichloromethane/methanol (7: 3 mixture) and then filtered. The solid was further washed with hot [ACETONITRILE/N,] [N-DIMETHYLFORMAMIDE] (9: 1 mixture) and finally acetonitrile. This afforded the title compound as a grey powder (25 mg, 18%). ‘H-NMR (DMSO-d6) : [B] 12.64 [(1H,] s); 9.66 [(1H,] s); 8.62 [(1H,] s); 8.27 (1H, s); 7.84 (2H, d); 7.52 (2H, t); 7.42 [(1H,] t); 2.10 (3H, s). [‘3C-NMR] (DMSO-d6) : [8] 147.3 ; 145.8 ; 134.0 ; 131.5 ; 129.9 ; 128.8 ; 128.7 ; 127.5 ; 118.8 ; 117.6 ; 110.1 ; 99.9 ; [22. 7.] APCI-MS m/z : 277.1 [[MH+].]

The chemical industry reduces the impact on the environment during synthesis 33252-28-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; WO2004/16609; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem