Category: pyridine-derivatives

Electric Literature of 116785-23-0, 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 116785-23-0, name is 4,6-Dimethylnicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

4,6-Dimethyl-3-pyridinecarbaldehyde1 (2.52g) and methyl D-alloisoleucinatehydrochloride (3.4g) were dissolved in 2,2,2-trifluoroethanol (50ml). To this wasadded triethylamine (2.61ml) and the reaction mixture was left to stand for 18 hours.

According to the analysis of related databases, 116785-23-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2006/399; (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. 183208-34-6, name is 5-Bromo-1H-pyrrolo[2,3-b]pyridin-2-one, the common compound, a new synthetic route is introduced below. name: 5-Bromo-1H-pyrrolo[2,3-b]pyridin-2-one

Step 3: 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrrolo[2,3-b]pyridin-2(3H)-one To a solution of 5-bromo-lH-pyrrolo[2,3-b]pyridin-2(3H)-one (3 g, 14.08 mmol) in 1,4-dioxane (60 mL) were added 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(l,3,2-dioxaborolane) (4.29 g, 16.9 mmol), potassium acetate (2.07 g, 21.12 mmol) and l,l’-bis(diphenylphosphino)ferrocene- palladium(II)dichloride (1.02 g, 1.41 mmol). The reaction mixture was purged with nitrogen for 2 min and heated to 110 C for 1 h. After cooling down the mixture was filtered and the solid was washed with ethyl acetate. The mother liquid was diluted with methanol and the precipitate was filtered and dried in vacuo to afford 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrrolo[2,3- b]pyridin-2(3H)-one (1.1 g, 30%): lU NMR (400 MHz, DMSO-d6) delta 11.14 (s, 1H), 8.29 (s, 1H), 7.68 (s, 1H), 3.54 (s, 2H), 1.29 (s, 12H).

The synthetic route of 183208-34-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; HUESTIS, Malcolm; KELLAR, Terry; PATEL, Snahel; SHORE, Daniel; SIU, Michael; (260 pag.)WO2016/142310; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 667932-24-3, Adding some certain compound to certain chemical reactions, such as: 667932-24-3, name is 2-Ethynylpyridin-4-amine,molecular formula is C7H6N2, 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 667932-24-3.

Step E Compound 240 (513 mg) was dissolved in dry dichloromethane (50 mL) and Et3N (0. 786ml, 1.3equiv.) was added under nitrogen. The mixture was cooled in an ice bath and a solution of dichloroacetyl chloride (0.483 mL, [L.] [LEQUIV.)] in dry dichloromethane (5 mL) was added dropwise. The reaction was allowed to warm to room temperature over 6 hours and then diluted with EtOAc, washed with a saturated solution of sodium bicarbonate, dried, filtered and concentrated in vacuo. The crude material was passed through a plug of silica gel, eluted with 1: 1 hexanes/EtOAc. The fractions were concentrated to produce a purple oil that solidified under high vacuum to yield compound 255 (658mg).

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. 667932-24-3, 2-Ethynylpyridin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; WO2004/18463; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 116855-08-4, 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 116855-08-4 as follows.

Step 5: lH-Pyrazolor3,4blpyridine-3-carboxylic Acid Methyl Ester The mixture of solids from the preceding step 4 (95 g) was suspended in methanol (500 mL) and sulfuric acid (5 mL) was added carefully. The reaction mixture was then heated to reflux for 6-8 h, and the reaction was monitored using TLC. After completion of the reaction, inorganic solids were filtered off from the reaction mixture and the solid cake was washed with hot methanol. The main filtrate and the washings were combined, then methanol was distilled off under reduced pressure on the rotary evaporator. The resulting solids were suspended in 5% sodium bicarbonate solution (300 mL) and stirred for 5 min. at room temperature. The white solids were filtered off and dried in an oven at 90-95 0C to constant weight (8.07 g, 42% based on 3-methyl-lH-pyrazolo[3,4b]pyridine), mp 201-203 0C. 1H NMR: (CDCl3) 14.4 (brs, 1 H), 8.74 (dd, J = 4.6 and 1.5 Hz, 1 H), 8.64 (dd, J = 8.1 and 1.5 Hz, 1 H), 7.39 (dd J = 8.1 and 4.6 Hz, 1 H), 4.10 (s, 3 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,116855-08-4, its application will become more common.

Reference:
Patent; UNIVERSITY OF KANSAS; GEORGE, Ingrid, Gunda; TASH, Joseph, S.; CHAKRSALI, Ramappa; JAKKARAJ, Sudhakar, R.; CALVET, James, P.; WO2011/5759; (2011); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 58602-02-1, 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.58602-02-1, name is 2,6-Difluoro-3-nitropyridine, molecular formula is C5H2F2N2O2, molecular weight is 160.0784, as common compound, the synthetic route is as follows.

EXAMPLE 4 1-(6-Fluoro-3-nitro-2-pyridinyl)-4-carbobenzoxypiperazine-2-carboxylic acid In a similar procedure to that described in Example 1, from 6.0 g. of 2,6-difluoro-3-nitropyridine, 9.0 g. of 4-carbobenzoxypiperazine-2-carboxylic acid, hydrochloride, 20 ml. of triethylamine and 150 ml. of dimethyl sulfoxide, there is obtained 14 g. of the title product as a viscous orange glass. Thin layer chromatographic analysis of this material shows essentially one spot.

The chemical industry reduces the impact on the environment during synthesis 58602-02-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; American Home Products Corporation; US4138564; (1979); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1227594-89-9 ,Some common heterocyclic compound, 1227594-89-9, molecular formula is C6H3F4NO, 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.

[00643] Step C: (1r,4r)-4-(6-(ethylamino)-3-(2-methyloxazol-5-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)cyclohexan-1-ol (0.0101 g, 0.0296 mmol), 3-fluoro-4-(trifluoromethyl)pyridin-2-ol (0.0161 g, 0.0887 mmol), PPh3 (0.0233 g, 0.0887 mmol) were dissolved in THF (0.5 mL) and then DIAD (0.0179 g, 0.0887 mmol) was added and stirred overnight and then concentrated. The residue was purified over preparative HPLC (5-95% ACN in water with 0.2% TFA) and concentrated to afford N-ethyl-1-((1s,4s)-4-((3-fluoro-4-(trifluoromethyl)pyridin-2-yl)oxy)cyclohexyl)-3-(2-methyloxazol-5-yl)-1H-pyrazolo[4,3-c]pyridin-6-amine bis(2,2,2-trifluoroacetate) (5.6 mg, 25.8 % yield). Mass spectrum (apci) m/z = 505.2 (M+H).1H NMR (CD3OD) delta 8.91 (s, 1H), 8.13 (d, 1H), 7.70 (s, 1H), 7.20 (m, 1H), 6.82 (s, 1H), 5.53 (s, 1H), 4.99 (m, 1H), 4.70 (m, 1H), 3.42 (q, J = 7.0 Hz, 2H), 2.61 (s, 3H), 2.53-2.30 (m, 4H), 1.96 (m, 4H), 1.36 (t, J = 7.0 Hz, 3H).

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. 1227594-89-9, 3-Fluoro-4-(trifluoromethyl)pyridin-2(1H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRAY BIOPHARMA INC.; ALLEN, Shelley; BOYS, Mark Laurence; COOK, Adam; GAUDINO, John; HINKLIN, Ronald Jay; LAIRD, Ellen; MCNULTY, Oren T.; METCALF, Andrew T.; NEWHOUSE, Brad; ROBINSON, John E.; (545 pag.)WO2019/113190; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1060814-91-6 ,Some common heterocyclic compound, 1060814-91-6, molecular formula is C9H10BrNO2, 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.

[0567] Step 2: ethyl 2-(4-bromopyridin-2-yl)-2-methylpropanoate – To a stirred solution of ethyl 2-(4-bromopyridin-2-yl)acetate (0.5 g, 2.05 mmol, 1.0 eq) in D F (5 mL) at 0C under nitrogen atmosphere was added NaH (60%) (0.246 g, 6.10 mmol, 3 eq). The reaction mass was stirred at rt for 30 mins, then cooled to 0C followed by the addition of methyl iodide (1.486 g, 10.25 mmol, 5.0 eq) under nitrogen atmosphere and stirred at RT for 16h. The DMF was removed under reduced pressure, water (10 mL) was added and the product extracted into EtOAc (3×15 mL). The combined organic extracts were dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a crude product which was purified by column chromatography to give ethyl 2-(4-bromopyridin-2-yl)-2-methylpropanoate (0.140g, 25%) as a pale yellow liquid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1060814-91-6, its application will become more common.

Reference:
Patent; CAPULUS THERAPEUTICS, LLC; GREEN, Michael John; HART, Barry Patrick; (341 pag.)WO2019/148125; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 6515-09-9, Adding some certain compound to certain chemical reactions, such as: 6515-09-9, name is 2,3,6-Trichloropyridine,molecular formula is C5H2Cl3N, 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 6515-09-9.

2,5,6-Trichloro-3-nitropyridine (Example 8) 3.6 g. (0.02 mol) of 2,5,6-trichloropyridine are dissolved in a mixture of 20 ml of 100% strength fuming nitric acid and 16 ml of concentrated sulphuric acid and are then heated at 100C in an oil bath for 12 hours. After cooling to approx. 20C, the reaction mixture is poured onto ice. The crude product is produced in the form of slightly yellowish crystals, which are filtered off with suction, washed with water and dried at 30C in vacuo over KOH. 3 g (66.7% of theory) of 2,5,6-trichloro-3-nitropyridine are obtained in the form of crystals which, after sublimation at 30 – 40C/12 mm Hg. melt at 68 – 70C. Analysis for C5 HCl3 N2 O2 (molecular weight 227.4): calculated C 26.41% H 0.44% Cl 46.77% N 12.32% found C 26.2% H 0.5% Cl 47.0% N 12.2%

According to the analysis of related databases, 6515-09-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ciba-Geigy Corporation; US3974166; (1976); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 60781-83-1, 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 60781-83-1 as follows.

General procedure: Genereal procedure for synthesis of 4a: A mixture of N-methyl-isatin 1 (2.0 mmol), 2-aminopyridine 2a (2.0 mmol) and [bmIm]OH (0.4 mmol) was stirred at room temperature for 2-5 h. After completion of reaction as indicated by TLC, 20 mL of water was added to the reaction mixture and stirred well. The product was extracted with EtOAc (3 × 20 mL). The combined organic layers were dried over anhydrous Na2SO4 to afford the crude product and recrystallized from ethanol to obtain analytically pure compound 4 (75-89%). After isolation of the product, the remaining aqueous layer containing the ionic liquid was washed with ether (2 × 10 mL) to remove organic impurities and filtered. The filtrate was extracted with dichloromethane (2 × 10 mL), dried over MgSO4 and evaporated under reduced pressure to afford [bmIm]OH, which was recycled twice in subsequent runs 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,60781-83-1, its application will become more common.

Reference:
Article; Siddiqui; Shamim, Shayna; Waseem, Malik Abdul; Abumhdi, Afaf A.H.; Srivastava, Arjita; Srivastava, Anjali; Tetrahedron Letters; vol. 54; 37; (2013); p. 5083 – 5086;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 65873-72-5, 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. 65873-72-5, name is 6-Methoxynicotinaldehyde, molecular formula is C7H7NO2, 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.

Starting materials of the formula (II) Example (II-1) STR13 9.5 g (0.069 mol) of 6-methoxy-nicotinaldehyde are suspended in 100 ml of water and chlorine is introduced at 45 C. until conversion is practically complete (about 2 hours). After cooling, the product, which isobtained in a crystalline form, is then isolated by filtering with suction. 9.4 g (79% of theory) of 5-chloro-6-methoxynicotinaldehyde of melting point152 C. are obtained.

According to the analysis of related databases, 65873-72-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bayer Aktiengesellschaft; US5051513; (1991); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem