Day: August 19, 2021

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

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

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

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

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

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. 1694-57-1, name is (2-Chlorophenyl)(pyridin-2-yl)methanone. A new synthetic method of this compound is introduced below., Safety of (2-Chlorophenyl)(pyridin-2-yl)methanone

2-chlorophenylpyridyl ketone (43.5mg, 0.2mmo l), dibromohein (57.2mg, 0.2mmol) and Pd (OAc) 2 (4.5mg, 0.02mmol), add 2mL of dichloroethane, The reaction was performed at 90C for 12 hours, and purified by thin layer chromatography to obtain 43.9 mg of 2-bromo-6-chlorophenylpyridylmethanone with a yield of 74.0%.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 1694-57-1, (2-Chlorophenyl)(pyridin-2-yl)methanone.

Reference:
Patent; China Three Gorges University; Liu Qixing; Chen Yongsheng; Zhang Yin; Chen Danyi; Wen Simiaomiao; Zhao Rongrong; Liu Yiheng; Zhou Haifeng; (14 pag.)CN110563641; (2019); A;,
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 36052-26-3, name is Methyl 6-aminopicolinate. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 36052-26-3

d) 6-Amino-5-bromo-pyridine-2-carboxylic acid methyl ester; To a solution of 6-amino-pyridine-2-carboxylic acid methyl ester (10 g, 66.0 mmol) in chloroform (450 mL) was added bromine (3.4 mL, 66.0 mmol) in CHCl3 (100 mL) at room temperature and stirred for 40 hours. The reaction mixture was diluted with CHCl3 and washed with saturated sodium thiosulfate solution and water. The organic phase was dried over sodium sulfate, the solvent was evaporated and the residue purified by silica gel column chromatography using ethyl acetate/hexane as eluent. The title compound obtained as yellow solid (3.3 g, 22%).MS ESI (m/e): 231.0 [(M+H)+].1H NMR (CDCl3, 400 MHz): delta(ppm)=7.76 (d, J=7.88 Hz, 1H), 7.34 (d, J=7.92 Hz, 1H), 5.23 (s, 2H), 3.94 (s, 3H).d) 6-Amino-3-bromo-pyridine-2-carboxylic acid methyl esterIn step d) the isomeric 6-amino-3-bromo-pyridine-2-carboxylic acid methyl ester (3.0 g, 19%) was isolated as side product.MS ESI (m/e): 231.2 [(M+H)+].1H NMR (CDCl3, 400 MHz): delta(ppm)=7.60 (d, J=8.72 Hz, 1H), 6.47 (d, J=7.88 Hz, 1H), 4.71 (s, 2H), 3.94 (s, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 36052-26-3.

Reference:
Patent; Baumann, Karlheinz; Goetschi, Erwin; Green, Luke; Jolidon, Synese; Knust, Henner; Limberg, Anja; Luebbers, Thomas; Thomas, Andrew; US2011/190269; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1173897-86-3, 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.1173897-86-3, name is 5-Bromo-6-methylpicolinonitrile, molecular formula is C7H5BrN2, molecular weight is 197.032, as common compound, the synthetic route is as follows.

An argon degassed solution of 5-bromo-6-methylpyridine-2-carbonitrile 13 (3.3 mmol, 650 mg), 4,4,5,5,-tetramethyl-2-vinyl-1,3,2-dioxaborolane (3.3 mmol, 0.56 mL), tetrakis(triphenylphosphine)palladium (5 mol %, 0.16 mmol, 190 mg) and 2N aqueous sodium carbonate solution (3.4 eq., 11.22 mmol, 5.60 mL) in toluene/ethanol (2:1, 45 mL) was heated at 95 C with stirring for 16 h. The slurry was cooled to RT, diluted with ethyl acetate and water. Organic layer was then separated. The organic layer was washed with brine and dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to afford the desired product which was purified by flash chromatography over silica gel using an elution of 20% ethyl acetate in hexane to give 246 mg (Yield: 52%) of the title compound 14 as an oil. 1H NMR (400 MHz, CDCl3): delta 7.81 (1H, d, J = 8.0 Hz), 7.52 (1H, d, J = 8.0 Hz), 6.89 (1H, dd, J = 17.6 & 10.8 Hz), 5.79 (1H, d, J = 17.2 Hz), 5.58 (1H, d, J = 10.8 Hz), 2.62 (3H, s); ESI-MS: m/z 145 [M + H]+

Statistics shows that 1173897-86-3 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-6-methylpicolinonitrile.

Reference:
Article; Nino, Patricia; Caba, Marta; Aguilar, Nuria; Terricabras, Emma; Albericio, Fernando; Fernandez, Joan-Carles; Indian Journal of Chemistry – Section B Organic and Medicinal Chemistry; vol. 55B; 9; (2016); p. 1117 – 1130;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 82454-61-3 ,Some common heterocyclic compound, 82454-61-3, molecular formula is C7H6N2, 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.

Copper (I) iodide (4.22 mg, 0.022 mmol) was added to a stirred mixture of 1-6 (1 g, 2.22 mmol), 5-ethynyl-2-pyridinamine (523.68 mg, 4.43 mmol), TEA (924.23 jiL, 6.65 mmol), PdC12(PPh3)2 (31.11 mg, 0.044 mmol) and PPh3 (11.63 mg, 0.044 mmol) in DMF (10 mL). The mixture was purged with N2 for 5 mm and then it was stirred at 90°C for 5 h. The residue was diluted with water and extracted with EtOAc. The organic layer was separated, dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by flash column chromatography (silica; MeOH/DCM 0/100 to 05/95). The desired fractions were collected and concentrated in vacuo to yield P-3 (923 mg, 92percent).

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. 82454-61-3, 5-Ethynylpyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ANDRES-GIL, Jose, Ignacio; VAN GOOL, Michiel, Luc, Maria; BORMANS, Guy, Maurits, R; VERBEEK, Joost; (42 pag.)WO2017/103182; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 14432-12-3 ,Some common heterocyclic compound, 14432-12-3, molecular formula is C5H5ClN2, 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 50 mL single necked round bottom flask equipped with a magnetic stirrer bar,reflux condenser and nitrogen line was charged with 2-chloropyridin-4-amine 12 (2.50 g, 19.4 mmol, 1.0 equiv), sodiumacetate trihydrate (3.97 g, 29.2 mmol, 1.5 equiv), iodine monochloride(3.47 g, 21.4 mmol, 1.1 equiv) and glacial acetic acid(13.0 mL) and heated at 70 C with magnetically facilitated stirring under nitrogen for 16 h, at which point tlc and GC/MS (EI) analysisshowed that the starting material had been consumed. The reactionmixture was cooled and transferred to a separating funnel where itwas carefully quenched with portion wise addition of solidpowdered sodium hydrogencarbonate (32.3 g), water (75 mL) and ethyl acetate (75 mL). The resultant effervescence was allowed to subside and the mixture was not shaken. The layers were thenseparated and the aqueous layer was extracted with ethyl acetate(6 x 25 mL), with shaking. The organic layers were combined anddried over magnesium sulfate and the solvent was removed viarotary evaporation. The residue was purified by portionwise flashcolumn chromatography over silica using n-hexane/ethyl acetate(94:6 to 60:40) mixtures as eluent to give 2-chloro-3-iodopyridin-4-amine 13 as a light brown solid (2.21 g, 45%), a sample of whichhad 1H NMR spectral data and low resolution GC/MS (EI) massspectral data identical to those in the literature [12].

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. 14432-12-3, 4-Amino-2-chloropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Balfour, Michael N.; Franco, Caio H.; Moraes, Carolina B.; Freitas-Junior, Lucio H.; Stefani, Helio A.; European Journal of Medicinal Chemistry; vol. 128; (2017); p. 202 – 212;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem