Category: pyridine-derivatives

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. 1702-17-6, name is 3,6-Dichloropicolinic acid, molecular formula is C6H3Cl2NO2, 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. Quality Control of 3,6-Dichloropicolinic acid

To a solution of compound 1(100 g, 520.8 mmol) in EtOH (400 mL) was added drop- wise SOd2 (155 g, 1.3 mol) at 0 C Then the mixture was stirred at 90 C for 2 h. TLC(PE:EA=3:1, Rf =0.5) showed the reaction was completed. The solvent was evaporated underreduced pressure. The mixture was add saturated NaHCO3 adjusted PH=7 and extracted with EA (200 ml*3). The combined organic layer was dried with Na2SO4, filtered and concentrated to give compound (120 g, 100%) as yellow oil. LC-MS (M+H) =220.

With the rapid development of chemical substances, we look forward to future research findings about 1702-17-6.

Reference:
Patent; BEIGENE, LTD.; WANG, Hexiang; ZHANG, Guoliang; GUO, Yunhang; REN, Bo; WANG, Zhiwei; ZHOU, Changyou; (219 pag.)WO2016/161960; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 109113-39-5 ,Some common heterocyclic compound, 109113-39-5, molecular formula is C13H10N2O2S, 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.

m-Chloroperoxybenzoic acid (~70%, 63 g, 369.7 mmol) was added in portions to a stirred solution of 3-2 (9.5 g, 36.9 mmol) in CHCI3 (250 mL) at room temperature, and the reaction mixture was stirred for 24 hours. The reaction mixture was cooled to 0C, and 10% aqueous sodium sulfite solution (50 mL) was added thereto followed by saturated aqueous NaHC03 solution. The organic layer was separated, and the aqueous layer was extracted with CH2C12 (50 mL. x 3). The combined organic layers were dried over anhydrous Na2S04, and concentrated under reduced pressure. The obtained residue was triturated with diethyl ether to give the desired product 3-3 as a creamy solid (8.5 g, 84%); LCMS: m/z 275.1 [ + 1].

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. 109113-39-5, 1-(Phenylsulfonyl)-1H-pyrrolo[3,2-c]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KOUL, Summon; KURHADE, Suresh; BHOSALE, Sandeep; NAIK, Keshav; SALUNKHE, Videsh; MUNOT, Yogesh; BHUNIYA, Debnath; (284 pag.)WO2015/88045; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 61889-48-3, 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. 61889-48-3, name is 2-Chloro-1-(pyridin-3-yl)ethanone hydrochloride. A new synthetic method of this compound is introduced below.

To a solution of (-)-B-chlorodiisopinocampheylborane [(-)-DIP-Cl] (25 g, 77.9 mmol) in tetrahydrofuran (90 ml) are added with stirring 3-(2-chloroacetyl)pyridine hydrochloride (Can. J. Chem., vol. 61, p. 334 (1983)) (3.0 g, 15.6 mmol) and triethylamine (2.39 ml, 17.2 mmol) at -25C, and the reaction mixture is stirred at -25C for 3 days. To this mixture is added water (300 ml), and the mixture is warmed to room temperature. To the mixture is added ethyl acetate, and the organic phase is separated. The aqueous phase is neutralized with a saturated aqueous sodium hydrogen carbonate solution, and extracted 6 times with ethyl acetate. The combined organic phase is dried over sodium sulfate, and concentrated under reduced pressure to give yellow oil, which is purified by silica gel column chromatography (methanol/chloroform = 1/20) to give the title compound (R)-2-chloro-1-pyridin-3-ylethanol (2.02 g, yield: 82 %) as pale yellow oil. 1H-NMR (CDCl3) delta: 2.75 (1H, d, J=3.4Hz), 3.67 (1H, dd, J=8.5, 11.3Hz), 3.78 (1H, dd, J=3.5, 11.3Hz),, 4.96-5.00 (1H,m), 7.33 (1H, dd, J=4.9, 7.9Hz), 7.75-7.78 (1H, m), 8.59 (1H, dd, J=1.6, 4.8Hz), 8.64 (1H, d, J=2.2Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,61889-48-3, its application will become more common.

Reference:
Patent; Sumitomo Pharmaceuticals Company, Limited; EP1514869; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 14237-71-9, 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 14237-71-9, name is 2-Chloro-4,6-dimethylnicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: In a 100 mL round bottom flask, compound 2a (0.7 g, 4.0 mmol),P-methylaniline (1.3 g, 12.0 mmol) and DMSO (15 mL) were stirred and heated in an oil bath at 120 under N2 protection(The progress of the reaction was monitored by TLC, developing solvent: ethyl acetate: petroleum petroleum = 1: 10). After the reaction is completed, cool to room temperature.Extract with saturated NaHCO3 solution (3 × 30 mL) and DCM solution (5 × 30 mL), combine the organic phases,Wash with saturated NaCl solution 3 ~ 4 times, dry with anhydrous Na2SO4, and concentrate under reduced pressure.Purification by silica gel column chromatography (eluent: V ethyl acetate: V petroleum ether = 1: 45) to obtain compound 3aa as a white powder. Yield: 39%.

According to the analysis of related databases, 14237-71-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guilin Medical University; Huang Wanyun; Zhang Xiaoting; Zheng Bin; Lv Liang; Wang Shuqin; (17 pag.)CN110305128; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 54916-66-4, 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. 54916-66-4, name is 5-Bromo-2-methoxynicotinic acid, molecular formula is C7H6BrNO3, 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.

To a solution of 5-bromo-2-methoxynicotinic acid (15 g, 64.6 mmol, commercially available from, for example, Combiblocks) in DCM (100 mL) cooled to 0 0C, was added oxalyl dichloride (16.98 mL, 194.0 mmol) followed by the slow addition of DMF (5.01 mL, 64.6 mmol) at 0 C. The reactionmixture was then stirred for 18 h at rt. A small aliquot of the reaction mixture was taken and quenched with MeOH, the TLC shows the complete conversion of SM. The reaction mixture was then concentrated and re-dissolved in DCM (150 mL) and treated with ethanamine hydrochloride (7.91 g, 97 mmol). The reaction mixture was stirred for 3 h at rt. After the reaction, water was added andthe organics extracted with ethyl acetate (2 x 300 mL). The organic layer was separated, dried over Na2504, filtered and concentrated to obtain the crude product. The crude product was purified by column chromatography on a silica gel 100-200 column and was eluted with l6% EtOAc/n-hexane. The collected pure fractions were concentrated under reduced pressure to afford the desired product 5-bromo-N-ethyl-2-methoxynicotinamide (11 g, 41.0 mmol, 64 % yield) as an off-whitesolid.LCMS (10 mm RND-FA-10-MIN): Rt = 4.22 mi [MH] = 261.LCMS Conditions: RND-FA- lO-MIN:Column: Acquity BEH C18 (100 mm x 2.1 mm, 1.7 pm)Mobile Phase: A: 0.05% formic acid in ACN; B: 0.05% formic acid in waterTime (mm) /%B: 0/97, 0.4/97, 7.5/2, 9.5/2, 9.6/97, 10/97Column Temp: 35 C, Flow Rate: 0.45 mL/min

According to the analysis of related databases, 54916-66-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen John; AYLOTT, Helen Elizabeth; COOPER, Anthony William James; DEMONT, Emmanuel Hubert; HARRISON, Lee Andrew; HAYHOW, Thomas George Christopher; LINDON, Matthew J; PRESTON, Alexander G; SEAL, Jonathan Thomas; WALL, Ian David; WATSON, Robert J; WOOLVEN, James Michael; (308 pag.)WO2017/37116; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 128071-98-7, 4-Bromo-2-fluoropyridine, 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, 128071-98-7, blongs to pyridine-derivatives compound. HPLC of Formula: C5H3BrFN

Compound 41.1. 4-Bromo-2-hydrazinylpyridine. To a solution of 4-bromo-2- fluoropyridine (2.0 g, 1 1.4 mmol) in pyridine (10 mL) was added hydrazine (5 mL, 159 mmol). The mixture was heated at 70 C for 2 hours, then cooled to room temperature. The volatile organics were removed under reduced pressure, then water (60 mL) was added to the residue and an off-white solid precipitated. The solid was filtered, washed with water, and dried under reduced pressure at 50 C to give 1.77 g (84%) of the title compound as an off- white solid, m/z (ES+) 188, 190 (M+H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,128071-98-7, its application will become more common.

Reference:
Patent; 3-V BIOSCIENCES, INC.; OSLOB, Johan D.; MCDOWELL, Robert S.; JOHNSON, Russell; YANG, Hanbiao; EVANCHIK, Marc; ZAHARIA, Cristiana A.; CAI, Haiying; HU, Lily W.; WO2014/8197; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1513-66-2 ,Some common heterocyclic compound, 1513-66-2, molecular formula is C5H3F2N, 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.

500 g of DMF was added to a 1000 mL four-necked flask, 100 g of compound A was charged,113.6 g of potassium carbonate and 5 g of tetrabutylammonium bromide, the temperature was raised to 60 C, and 92.6 g of the product was added dropwise2,3-difluoropyridine in 50 g of DMF in a mixed solution at a controlled temperature of 65 to 70 C,The reaction is about 2 hours, the reaction is completed, added to 1000 g of water, the pH is adjusted to 7 to 8 with hydrochloric acid,Stirring for 1 hour, filtering, solid is the etherification (compound I), drying.

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. 1513-66-2, 2,3-Difluoropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Jiangsu Fuding Chemical Co., Ltd.; Liu Dongwei; Cheng Lizhong; Chang Qing; Dong Hailong; Zhu Ruiyu; Gu Junkun; (16 pag.)CN106632045; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 55314-16-4, 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 55314-16-4 as follows.

A mixture of 65 g (0.156 moles) of 4-methyl-N-[3-(4-methyl-1H-imidazol-1-yl-5-(trifluoromethyl)phenyl]-3-guanidino-benzamide from step (c), 30.0 g (0.171 moles) of 3-dimethylamino-1-(3-pyridyl)-2-propen-1-one of the formula (VIII) in 650 ml n-butanol was heated at 110-115 C. for 9 hours. Reaction mass was brought to room temperature and the separated solid (70 g) was filtered off. Wet solid was leached with hot water (700 ml) and hot methanol (700 ml) successively. The wet product was dried at 60-65 C. under vacuum to yield compound of formula (I). Yield: 52.1 g (63%) MR: 235-236 C. Purity: 99.0% (by HPLC)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,55314-16-4, its application will become more common.

Reference:
Patent; Natco Pharma Limited; Kompella, Amala; Bhujanga Rao, Adibhatla Kali Satya; Rachakonda, Sreenivas; Gampa, Venugopala Krishna; Nannapaneni, Venkaiah Chowdary; US2013/210847; (2013); 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. 174669-74-0, name is 2-Fluoropyridin-3-ol, molecular formula is C5H4FNO, 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 2-Fluoropyridin-3-ol

To a suspension of sodium hydride (0.129 g, 3.21 mmol) in DMF (10 mL) at 0 C was dropwise added a stuffing solution of 2-fluoropyridin-3-ol (0.363 g, 3.21 mmol) in DMF (5 mL), then followed by the dropwise addition of the solution of 2-(2-(2-(2- azidoethoxy)ethoxy)ethoxy)ethyl 4-methylbenzenesulfonate (1.00 g, 2.68 mmol) in DMF (5 mL). The suspension was held at 0 C for 10 mm, then brought to ambient temperature for 1 hour, followed by additional heating at 60 C for 4 hours. The solvent was removed in vacuo. 100 ml of ethyl acetate was added followed by 3 separate wash extractions with concentrated brine solution. The organic layer was dried over sodium sulfate, filtered, and concentrated. The crude material was purified using flash chromatography (IscoCombiFlash – eluted with 10 – 50% EtOAc in Hex) to give a colorless oil. 3-(2-(2-(2-(2- azidoethoxy)ethoxy)ethoxy)ethoxy)-2-fluoropyridine (702 mg, 2.233 mmol, 83 % yield) was isolated as a clear oil. ?H NMR (400MHz, CHLOROFORM-d) oe 7.75 (dt, 1=4.9, 1.6 Hz, 1H), 7.33 (ddd, 1=10.0, 8.1, 1.5 Hz, 1H), 7.10 (ddd, 1=7.9, 4.9, 0.7 Hz, 1H), 4.30 – 4.16 (m, 2H),3.95 – 3.83 (m, 2H), 3.80 – 3.61 (m, 1OH), 3.38 (t, 1=5.1 Hz, 2H) 13C NMR (101MHz, CHLOROFORM-d) d 142.3, 137.7, 137.5, 123.4, 123.4, 121.7, 121.6, 77.3, 76.7, 70.9, 70.7, 70.6, 70.0, 69.4, 69.0, 50.6 19F NMR (400MHz, CHLOROFORM-d) oe -83.55. HRMS (ESI) Theory:C 1 3H20FN404+ mlz 315.464; found 315.1463.

With the rapid development of chemical substances, we look forward to future research findings about 174669-74-0.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MORIN, Paul, E.; DONNELLY, David; LIPOVSEK, Dasa; GOKEMEIJER, Jochem; JURE-KUNKEL, Maria, N.; FABRIZIO, David; WRIGHT, Martin, C.; DISCHINO, Douglas; BONACORSI, Samuel, J.; SMITH, Ralph, Adam; LAFONT, Virginie; (0 pag.)WO2016/86021; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 78607-36-0 ,Some common heterocyclic compound, 78607-36-0, 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.

Dissolve 2-chloro-3-iodopyridine (2.0 g, 8.37 mmol) in toluene (7 mL). Add piperazine-1-carboxylic acid t-butyl ester (1.2 g, 6.4 mmol), followed by the addition of tris(dibenzylideneacetone)dipalladium(0) (0.12 g, 0.13 mmol), 4,5-bis(diphenyl- phosphino)-9,9-dimethylxanthene (0.23 g, 0.39 mmol), and sodium t-butoxide (0.93 g, 9.7 mmol). Heat at 100 0C for 3.5 hr. Concentrate and partition the residue between EtOAc and water. Extract the aqueous phase twice with ethyl acetate. Wash combined organic layers with brine. Dry the organic extracts (sodium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 0: 100 to 20:80 ethyl acetate:hexanes), to give the title preparation (95%). MS (ES): m/z = 298 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,78607-36-0, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; WO2009/29439; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem