Category: pyridine-derivatives

Reference of 3222-50-2, 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. 3222-50-2, name is 4-Methylnicotinic acid. A new synthetic method of this compound is introduced below.

General procedure: Into a 1L open reactor was added 500g of carboxylic acid raw material (chemically pure) and stirring was turned on (600 r/min) from the reactorThe bottom is continuously fed with ammonia gas (chemical purity, water content of 5.1% by weight, flow rate of 100 g/min) to the carboxylic acid feed. After the reaction was allowed to proceed for TC hours at the reaction temperature TA, ammonia gas flow was stopped. The contents of the reactor were sampled and subjected to nuclear magnetic proton and elemental analysis to characterize the amide intermediate. Specific reaction conditions and characterization results are shown in Table A-1, Table A-2, Table A-3, Table A-4, Table A-5 and Table A-6. These characterization results show that the amide intermediates obtained have an extremely high purity (above 99%).In this embodiment, the ammonia gas can be directly replaced with waste ammonia gas (from Yangzi Petrochemical Plant, containing approximately50wt% of ammonia gas, the rest were toluene, oxygen, nitrogen, steam, carbon monoxide, and carbon dioxide, and the flow rate of this waste ammonia was 130g/min).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3222-50-2, 4-Methylnicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; Sinopec Yangzi Petrochemical Co., Ltd.; Sinopec Corporation; Sun Hailong; Wei Yanyu; Gao Yilong; Chen Xinhua; Miao Jun; Li Na; Kan Lin; Bai Jiye; Chen Shaohui; Yang Aiwu; Xu Yuexing; (76 pag.)CN104557357; (2018); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 22282-99-1 , The common heterocyclic compound, 22282-99-1, name is 4-Bromo-2-methylpyridine, molecular formula is C6H6BrN, 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 solution of 4-bromo-2-methyl-pyridine (2.00 g, 11.6 mmol, CAS 22282-99- 1) and diethyl carbonate (1.65 g, 13.9 mmol, 1.68 mL) in THF (15.0 mL) was added LDA (2 M, 11.63 mL) at -60 C dropwise. Then the mixture was stirred at -60 C for 2 hours. On completion, the reaction mixture was quenched by addition of saturated ammonium chloride solution 30 mL at 0 C, and extracted with ethyl acetate 60 mL (3 X 20 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under in vacuo to give a residue. The residue was purified by column chromatography (petroleum ether:ethyl acetate = 20:1 to 8:1) to give the title compound (1.30 g, 46% yield) as a yellow oil.1H NMR (400MHz, CDCl3) delta = 8.40 (d, J = 5.2 Hz, 1H), 7.52 (d, J = 1.6 Hz, 1H), 7.40 (dd, J = 1.6, 5.2 Hz, 1H), 4.21 (q, J = 7.2 Hz, 2H), 3.83 (s, 2H), 1.29 (t, J = 7.2 Hz, 3H).

The synthetic route of 22282-99-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RAZE THERAPEUTICS, INC.; MAINOLFI, Nello; (215 pag.)WO2018/106636; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 52311-50-9, 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. 52311-50-9, name is 2-Chloro-4-ethoxypyridine, molecular formula is C7H8ClNO, 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.

6.01.22.02 1-(4-ethoxy-pyridin-2-yl)-piperazine hydrochloride 860 mg piperazine was added to 350 mg 2-chloro-4-ethoxy-pyridine in 3.5 mL n-butanol. The reaction was stirred 1.5 days at 115 C. The reaction was filtered and the filtrate was washed with water and evaporated. 1N HCl was added to the residue and the precpipate was filtered to give 238 mg of the desired product. Rt: 0.3 min (method B), (M+H)+: 208

According to the analysis of related databases, 52311-50-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Boehringer Ingelheim International GmbH; GRAUERT, Matthias; BISCHOFF, Daniel; DAHMANN, Georg; KUELZER, Raimund; RUDOLF, Klaus; US2013/184248; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 139585-48-1, name is 2-Chloro-5-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 139585-48-1

a) 5′-Methoxy-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid ethyl ester To a stirred solution of piperidine-4-carboxylic acid ethyl ester (0.52 g, 3.34 mmol) and 2-chloro-5-methoxy-pyridine in 10 mL of toluene was added (13 mg, 0.057 mmol) of Pd(II) acetate, (17 mg, 0.027 mmol) of BINAP and tBuOK (0.44 g, 3.90 mmol). The mixture was heated at 120 C. for two hours, concentrated under vacuo and the residue was directly purified on column chromatography (SiO2, EtOAc/Hept 1:2) yielding 0.17 g (24%) of the title compound as a light yellow oil. ES-MS m/e: 265.3 (M-41′).

With the rapid development of chemical substances, we look forward to future research findings about 139585-48-1.

Reference:
Patent; Jablonski, Philippe; Knust, Henner; Nettekoven, Matthias; Patiny-Adam, Angelique; Ratni, Hasane; Riemer, Claus; US2011/53948; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 116355-18-1, name is 6-Bromo-7-methylimidazo[1,2-a]pyridine. This compound has unique chemical properties. The synthetic route is as follows. name: 6-Bromo-7-methylimidazo[1,2-a]pyridine

To a solution of 6-bromo-7-methylimidazo[1 ,2-a]pyridine (100 mg, 0.47 mmol) in CH2CI2 (1 mL), was added 1-lodopyrrolidine-2,5-dione (84 mg, 0.47 mmol) and MeOH (0.1 mL). The resulting mixturewas stirred at room temperature for 2 h. The reaction was poured into water and extracted with ethyl acetate. The organic phase was dried over Na2504, filtered, and concentrated in vacuo. The residue was purified by SiC2 column chromatography (hexane/EtOAc = 1:1) to give 122 mg (77 %) of the product as a white solid. LC/MS m/z: 337.00 (M+H).

With the rapid development of chemical substances, we look forward to future research findings about 116355-18-1.

Reference:
Patent; ARISAN THERAPEUTICS INC.; PLEWE, Michael; BROWN, Eric; GANTLA, Vidyasagar; HENKEL, Gregory; MCCORMACK, Kenneth; SOKOLOVA, Nadzeda V.; SHIN, Young-Jun; (147 pag.)WO2018/13430; (2018); A2;,
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. 2739-98-2, name is Ethyl 2-Pyridylacetate, the common compound, a new synthetic route is introduced below. COA of Formula: C9H11NO2

1b) 2-Hydroxypyrazolo[1,5-a]pyridine (C4f); The synthesis of 2-hydroxypyrazolo[1,5-a]pyridine was done according to literature (Ochi, M.; Miyasaka, T.; Kanada, K.; Arakawa, K. Bull. Chem. Soc. Japan, (1976), 49, 1980-1984).; A solution of 4.14 g (36.6 mmol) hydroxylamine-O-sulfonic acid in 13.8 ml water was neutralized with KOH (2.6 N) at 0C and added dropwise to 26.2 ml (0.172 mol) ethyl 2-pyridylacetate. After stirring for 30 h at room temperature the mixture was extracted with dichloromethane, the aqueous layer was adjusted to pH 9 with Na2CO3 solution (10%) and extracted with dichloromethane. Then, the aqueous layer was adjusted to pH 5 with acetic acid, extracted with dichloromethane, the organic layer was dried with MgSO4 and evaporated. The crude product was purified by flash-chromatography (hexane/EtOAc 90:10). Yield: 607 mg (39 %) white solid. Mp.: 127-128C. MS (APCI): m/z 135 (M+1)+. 1H NMR (DMSO-d6, 360 MHz) delta (ppm): 5.72 (d, J = 0.8 Hz, 1 H, H-3); 6.63 (ddd, J = 6.8 Hz, 6.8 Hz, 1.4 Hz, 1 H, H-6); 7.08 (ddd, J = 8.9 Hz, 6.8 Hz, 1.1 Hz, 1 H, H-5); 7.35 (ddd, J = 8.9 Hz, 1.4 Hz, 0.8 Hz, 1 H, H-4); 8.32 (dd, J = 6.8 Hz, 1.1 Hz, 1 H, H-7); 10.40 (s, 1 H, OH).

The synthetic route of 2739-98-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHWARZ PHARMA AG; EP1972628; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 68175-07-5, Adding some certain compound to certain chemical reactions, such as: 68175-07-5, name is 2-Methyl-1H-imidazo[4,5-b]pyridine,molecular formula is C7H7N3, 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 68175-07-5.

2-methyl-3H-imidazo[4,5-bjpyridine (10.8 g, 81 mmol) was mixed in EtOAc (500 mL) to give a partial suspension and mCPBA (18.66 g, 81 mmol) was added in portionsover 15 minutes. The resulting mixture was stirred at rt for 1.5 h. LCMS analysis indicated reaction was only 85percent complete, therefore an addition amount of mCPBA (2.2 g) was added. After stirring an additional 30 mm at a, the resulting precipitate which had formed was collected by filtration, rinsed with additional cold EtOAc (50 mL x 3) and dried under vacuum to afford 12 g (99percent) of the desired product as a tan solid.?H NMR (400 MHz, METHANOL-d4): oe 8.24 (dd, J=6.4, 0.7 Hz, 1H), 7.74 (d, J7.9 Hz,1H), 7.31 (dd, J=8.1, 6.4 Hz, 1H), 2.67 (s, 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. 68175-07-5, 2-Methyl-1H-imidazo[4,5-b]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WROBLESKI, Stephen T.; WEINSTEIN, David S.; YANG, Michael G.; (73 pag.)WO2018/81488; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1111637-74-1 ,Some common heterocyclic compound, 1111637-74-1, molecular formula is C7H5BrFNO, 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: (R,Z)-N-(1-(5-bromo-2-fluoropyridin-3-yl)ethylidene)-2-methylpropane-2-sulfinamide (5b) A mixture of 1-(5-bromo-2-fluoropyridin-3-yl)ethanone (5a, synthesized according to procedures described in WO2009016460; 11 g, 50.5 mmol), (R)-2-methylpropane-2-sulfinamide (Ak Scientific, 12.23 g, 101 mmol) and titanium (IV) ethoxide (Aldrich, 26.1 ml, 126 mmol) in THF (100 mL) was heated to reflux for 2 h. The mixture was cooled to room temperature, and brine (200 mL) was added. The suspension was vigorously stirred for 10 min. The suspension was filtered through a pad of silica gel and the organic phase was separated. The aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography (gradient 0-20% EtOAc/hexanes) to afford the title compound as a bright yellow oil (16 g, 49.8 mmol, 99% yield). MS m/z=320.8 [M+H]+; Calculated for C11H14BrFN2OS: 320.0

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. 1111637-74-1, 1-(5-Bromo-2-fluoropyridin-3-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MINATTI, Ana Elena; LOW, Jonathan D.; ALLEN, Jennifer R.; CHEN, Jian; CHEN, Ning; CHENG, Yuan; JUDD, Ted; LIU, Qingyian; LOPEZ, Patricia; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert M.; TAMAYO, Nuria A.; XUE, Qiufen; YANG, Bryant; ZHONG, Wenge; US2014/249104; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1227489-68-0 ,Some common heterocyclic compound, 1227489-68-0, molecular formula is C7H5F3N2O2, 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.

A mixture of 2-amino-4-(trifluoromethyl)nicotinic acid (74.0 mg, 0.359 mmol) and 50% aq. chloroacetaldehyde (0.093 mL, 0.718 mmol) was heated to 80 C for 18 h. The reaction mixture was concentrated in vacuo to yield the title compound. MS: m/z = 231 (M + 1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1227489-68-0, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott; COOKE, Andrew; STUMP, Craig; WILLIAMS, Peter; WO2014/113303; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1017183-06-0, 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 1017183-06-0, name is 2-Methyl-3-(pyridin-2-yl)propanoic acid. This compound has unique chemical properties. The synthetic route is as follows.

DIPEA (63.6 mu, 0.365 mmol) was added to a mixture of 2-methyl-3-(pyridin-2- yl)propanoic acid (60.4 mg, 0.365 mmol), 4-(3,5-dimethylisoxazol-4-yl)-Nl- (tetrahydro-2H-pyran-4-yl)benzene-l,2-diamine (100 mg, 0.348 mmol) and 2-(3H- [l,2,3]triazolo[4,5-b]pyridin-3-yl)-l, l,3,3-tetramethylisouronium hexafluorophosphate(V) (139 mg, 0.365 mmol) in DMF (lmL). The reaction mixture [ 5 was stirred at rt for 18h. DCM (lOmL) and saturated sodium bicarbonate solution (5mL) were added and the reaction mixture shaken thoroughly. The organic phase was collected, washed with brine (lOmL) and collected via PhaseSep cartridge. The solvent was removed in vacuo to afford a loose brown solid, which was redissolved in acetic acid (lmL) and heated to 80C with stirring for 72h. After cooling to rt, methanol 10 (5mL) was added and the solution was treated to SCX chromatography; eluting the compound with 1% ammonia in methanol solution. The ammoniacal eluent was concentrated in vacuo and the crude residue was purified by chromatography (4g silica, 0-10% methanol in DCM, gradient elution) to afford 3,5-dimethyl-4-(2-(l-(pyridin-2- yl)propan-2-yl)-l-(tetrahydro-2H-pyran-4-yl)-lH-benzo[d]imidazol-5-yl)isoxazole (20 15 mg, 13%) as an off white solid; Rt 1.29 min (Method 1), m/z 417 (M+H)+ (ES+); 1H MR (d6-DMSO) delta: 8.49 (ddd, J = 4.8, 1.9, 0.9 Hz, 1H), 7.71 – 7.55 (m, 3H), 7.26 – 7.08 (m, 3H), 4.71 (dd, J = 13.6, 9.4 Hz, 1H), 4.14 – 3.88 (m, 3H), 3.64 – 3.45 (m, 2H), 3.43 – 3.26 (m, 28H), 3.20 – 3.08 (m, 2H), 2.39 (s, 4H), 2.22 (s, 3H), 1.78 (d, J = 12.8 Hz, 1H), 1.48 – 1.31 (m, 4H)

According to the analysis of related databases, 1017183-06-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CELLCENTRIC LTD; PEGG, Neil Anthony; TADDEI, David Michel Adrien; ONIONS, Stuart Thomas; TSE, Eric Sing Yuen; BROWN, Richard James; MYCOCK, David Kenneth; COUSIN, David; PATEL, Anil; (135 pag.)WO2016/170324; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem