Day: April 12, 2022

Application of 60010-03-9, 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. 60010-03-9, name is 2,6-Dichloro-4-methyl-3-nitropyridine. A new synthetic method of this compound is introduced below.

6-chloro-2-(4,4-difluoro-1 -piperidyl)-4-methyl-3-nitro-pyridine (Intermediate com- pound)A solution of 2,6-dichloro-4-methyl-3-nitropyhdine (4.5g;21.7 mmol), 4,4- Difluoropiperidine (3.97g; 1.1 eq) and TEA (12ml; ca.4eq) in MeCN (30ml) was stirred at rt over night after which the reaction mixture was quenched with sat.NaHCOs(aq) solution and extracted with EtOAc (3x 5OmL). The combined or- ganic. were washed with brine, dried over Na2SO4(s), filtered and evaporated in vacuo to give 6.27g yellow solid (90% pure title compound)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,60010-03-9, its application will become more common.

Reference:
Patent; NEUROSEARCH A/S; BROWN, William, Dalby; JESSEN, Carsten; MATTSSON, Cecilia; SOTT, Richard; STRØBAeK, Dorte; WO2010/122064; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 77199-09-8, 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. 77199-09-8, name is Ethyl 5-bromopicolinate, molecular formula is C8H8BrNO2, 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.

A suspension of 5-bromo-2-pyridinecarboxylic acid (1.0 g, 4.95 mmol) and thionyl chloride (1.4 mL, 19.8 mmol) was heated at 70 C. for 2 hours. The reaction was cooled to room temperature and the excess thionyl chloride was removed under a stream of nitrogen. Toluene (5 mL) and ethanol (2.91 mL, 49.5 mmol) were added and heated at 80 C. for 18 hours. Excess ethanol was removed under reduced pressure. Ethyl acetate was added and the mixture was neutralized with sat. NaHCO3. The organic layer was washed with water and sat. NaCl. Extract was dried over MgSO4, filtered and solvent removed under reduced pressure to give 1.07 g of ethyl 5-bromopicolinate.Ethyl 5-bromopicolinate (1.0 g, 4.35 mmol) was mixed with 4.3 mL hydrazine and 4 mL ethanol and heated at 90 C. for 70 minutes then the excess reagent and ethanol was removed with a stream of nitrogen. The wet solid was triturated with ether then 90:10 Ether:MeOH to give a gray/green solid which was dried on the vacuum pump. The yield of 5-bromopicolinohydrazide was 0.536 g.5-Bromopicolinohydrazide (0.2 g, 0.926 mmol) was mixed with 0.4 mL acetic acid and 4.0 mL phosphorus oxychloride and heated at 100 C. for 1 hour then at 120 C. for 1.5 hours. Excess reagents were removed with a stream of nitrogen. The residue was dissolved in ethyl acetate and sat. NaHCO3 was added until the mixture was slightly basic. The organic layer was washed again with sat. NaHCO3, water and finally sat. NaCl. The organic layer was dried over MgSO4, filtered and solvent was removed under reduced pressure to give 0.236 g of 2-(5-bromopyridin-2-yl)-5-methyl-1,3,4-oxadiazole.2-(5-Bromopyridin-2-yl)-5-methyl-1,3,4-oxadiazole e (0.222 g, 0.925 mmol) was mixed with 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.226 g, 0.971 mmol), palladium tetrakis triphenyl phosphine (0.012 g, 0.046 mmol), 2M K3PO4 (0.957 mL), and 3.2 mL dioxane. The reaction was purged with nitrogen, sealed in a tube and put in an oil bath at 95 C. under a balloon filled with nitrogen for 18 hours. The reaction was cooled to room temperature and filtered through a plug of Celite washing with water and ethyl acetate. The layers were separated and the water layer was extracted with ethyl acetate (2×25 mL). The combined organic layers were washed with 20 mL sat. NaCl, dried with MgSO4, filtered and solvent removed under reduced pressure. The crude product was purified by column chromatography on 100 mL Silica Gel eluting with 100% ethyl acetate followed by 90:10 ethyl acetate:MeOH to give 0.147 g of 4-methyl-3-(6-(5-methyl-1,3,4-oxadiazol-2-yl)pyridin-3-yl)aniline.Phosgene solution (0.146 mL, 0.278 mmol) in 1 mL DCM was cooled to 0 C. A solution of 4-(2-amino-5-tert-butylthiophene-3-carbonyl)-1,3,3-trimethylpiperazin-2-one (0.030 g, 0.093 mmol) in 1 mL DCM was added to the cooled phosgene solution over 5 minutes. The ice bath was removed and after 20 minutes the reaction was checked by LC/MS. The excess phosgene and solvents were removed in a stream of Nitrogen and the residue was taken up in 1 mL of DCM. 4-Methyl-3-(6-(5-methyl-1,3,4-oxadiazol-2-yl)pyridin-3-yl)aniline (0.024 g, 0.090 mmol) and DIEA (0.019 mL, 0.107 mmol) were mixed with 1 mL DCM and cooled in salt ice bath. The carbamoyl chloride solution was added dropwise to the amine solution. LC/MS of the reaction mixture 20 minutes later showed completion of the reaction. The reaction was diluted with DCM and washed with sat. NaHCO3, water and sat. NaCl. The combined organic layers were dried over MgSO4, filtered and solvent removed under reduced pressure. Purification by column chromatography on silica gel eluting with 90:10 ethyl acetate:Hex then 100% ethyl acetate gave the material contaminated with some residual aniline. This material was dissolved in DCM and two drops of Acetyl chloride were added to form the acetate of the aniline impurity. The reaction was run for 30 minutes then it was diluted with DCM and washed with sat. NaHCO3 and sat. NaCl. The organic layers were dried over MgSO4, filtered and solvent removed under reduced pressure. The solid was purified by column chromatography on silica gel eluting with 100% ethyl acetate to give 0.0168 g of 1-(5-tert-butyl-3-(2,2,4-trimethyl-3-oxopiperazine-1-carbonyl)thiophen-2-yl)-3-(4-methyl-3-(6-(5-methyl-1,3,4-oxadiazol-2-yl)pyridin-3-yl)phenyl)urea.H-1 NMR (400 MHz, CDCl3): (ppm) 10.05 (s, 1H), 8.70 (d, J=1.4 Hz, 1H), 8.24 (d, J=8.2 Hz, 1H), 7.85 (dd, J=8.2, 2.1 Hz, 1H), 7.75 (s, 1H), 7.45 (d, J=2.1 Hz, 1H), 7.30 (dd, J=8.2, 2.3 Hz, 1H), 7.21 (d, J=8.4 Hz, 1H), 6.40 (s, 1H), 3.73 (t, J=5.0 Hz, 2H), 3.46 (t, J=5.0 Hz, 2H), 3.02 (s, 3H), 2.67 (s, 3H), 2.22 (s, 3H), 1.72 (s, 6H), 1.31 (s, 9H).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 77199-09-8, Ethyl 5-bromopicolinate.

Reference:
Patent; LOCUS PHARMACEUTICALS, INC.; US2010/41642; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1092286-30-0, 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.1092286-30-0, name is 5-Chloro-2-methyl-3-pyridinecarboxylic acid, molecular formula is C7H6ClNO2, molecular weight is 171.58, as common compound, the synthetic route is as follows.

Example 3.1 and 3.2Trans-5-Chloro-N-[4-(5,6-dihydro-4H-cyclopentapyrazol-1 -ylmethyl)- cyclohexyl]-2-methyl-nicotinamide and Trans-5-Chloro-N-[4-(5,6-dihydro-4H- cyclopentapyrazol-2-ylmethyl)-cyclohexyl] -2-methyl-nicotlnamideTrans-4-(5,6-dihydro-4H-cyclopentapyrazof-1-ylrriethyl)-cydohexylamine(intermediate H) (118 mg, 0.461 mmol) was suspended in DMF (2 ml) and treated with 5-chloro-2-methyl-nicotinic acid (96 mg, 0.461 mmol) and HATU (210 mg, 0.554 mmol) . DIPEA (0.321 ml, 1.845 mmol) was added and the reaction mixture was stirred at RT for 1 hour. The mixture was partitioned between DC and water and the organic phase was separated and washed with water, brine, dried (MgS04) and the solvent was removed in vacuo. The crude product was purified by chromatography on basic Alumina, eluting with a iso-hexane/EtOAc to afford a -1: 1 mixture of regiosisomers.LCMS Rt = 2.15 min; [M+H 373. Method LowpH_v002. The mixture was separated using by SFC using conditions described in the ‘General Conditions’ section.Ex. 3.1 : Trans-5-Chloro-N-[4-(5,6-dihydro-4H-cyclopentapyrazol-1-ylmethyl)- cyclohexyl]-2-methyl-nicotinamide:1 H N R (500MHz, DMSO) delta 8.52 (1 H, d), 8.40 (1 H, d), 7.78 (1 H, d), 7.06 (1H, s), 3.80 (2H,d) 3.66 (1H, m), 2.66 (2H, m), 2.51 (2H, m), 2.47 (3H, s), 1.91 (2H, m), 1.73 (1H, m), 1.59 (2H, m), 1.21 (2H, m), 1.08 (2H, m).Ex. 3.2: Trans-5-Chloro-N-[4-(5,6-dihydro-4H-cyclopentapyrazol-2-ylmethyl)- cyclohexyl] -2-methyl-nicotinamide:1 H NMR {500MHz, DMSO) delta 8.52 (1 H, d), 8.40 (1 H, d), 7.78 (1 H, d), 7.27 (1 H, s), 3.83 (2H,d) 3.65 (1H, m), 2.53 (2H, m), 2.48 (3H, s), 2.30 (2H, m), 1.89 (2H, m), 1.71 (1H, m), 1.58 (2H, m), 1.20 (2H, m), 1.05 (2H, m).

Statistics shows that 1092286-30-0 is playing an increasingly important role. we look forward to future research findings about 5-Chloro-2-methyl-3-pyridinecarboxylic acid.

Reference:
Patent; NOVARTIS AG; BEATTIE, David; BRUCE, Ian; COLSON, Anny-Odile; CULSHAW, Andrew James; SHARP, Thomas; WO2011/95450; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1239880-00-2, 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. 1239880-00-2, name is 6-Bromoimidazo[1,5-a]pyridine, molecular formula is C7H5BrN2, 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 mixture of AICI3 (798 mg, 6.0 mmol) in dry DCM (12 mL) at 0C was added dropwise acetyl chloride (471 mg, 6.0 mmol). The mixture was stirred at 0C for 10 min, followed by dropwise addition of a solution of 6- bromoimidazo[l,5-a]pyridine (400 mg, 2.0 mmol) in dry DCM (3 mL). The resulting mixture was stirred at 0C for 0.5 hr then poured into ice -water (20 g) and extracted with DCM. The combined organic layers were washed with brine, dried over anhydrous Na2SC>4, and concentrated under reduced pressure. The residue was purified by flash column chromatography to give the desired product (130 mg, 27% yield) as a yellow solid. LC-MS: m/z 239, 241 (M+H)+.

According to the analysis of related databases, 1239880-00-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SPERO THERAPEUTICS, INC.; ZAHLER, Robert; (262 pag.)WO2016/112088; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 59576-31-7, 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. 59576-31-7, name is 1-(4,6-Dimethylpyridin-2-yl)ethanone, molecular formula is C9H11NO, 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.

Example 7: Preparation of compound P.10l-(4,6-Dimethyl-pyridin-2-yl)-ethanone (400mg) was dissolved in methanol (15ml_) and (E)-l-[6-(3-aminooxy-propyl)-pyridin-2-yl]-ethanone O-methyl-oxime (600mg) was added. After stirring for 70h at ambient temperature, the reaction mixture was concentrated and the residue was purified by chromatography over silica to give colorless oil (740mg). ^-NMR (CDCI3, 400 MHz):7.70 (d, IH), 7.55 (t, IH), 7.47 (s, 2H), 7.11 (d, IH), 6.93 (s, IH), 4.28 (t, 2H), 4.01 (s, 3H), 2.92 (t, 2H), 2.51 (s, 3H), 2.32 (s+s+s, 9H), 2.21 (m, 2H)

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 59576-31-7, 1-(4,6-Dimethylpyridin-2-yl)ethanone.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; ZAMBACH, Werner; STIERLI, Daniel; NEBEL, Kurt; BORTOLATO, Andrea; MASSOL-FRIEH, Clara; WO2012/38521; (2012); 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. 15103-48-7, name is Pyridine-2-sulfonic acid, the common compound, a new synthetic route is introduced below. SDS of cas: 15103-48-7

Take 1.0 g of compound Int-14 prepared in the fifth step of Example 2 and 325 mg of 2-pyridine sulfonic acid, 140 mg of anhydrous potassium carbonate, and 50 ml of 1,4-dioxane, and heat and reflux the reaction for 12 hours. After concentration under reduced pressure, the residue was separated and purified by silica gel column to give 0.8 g of compound CJH-IRPS-09 as a black solid.

The synthetic route of 15103-48-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shijiazhuang Cheng Zhiyonghua Display Materials Co., Ltd.; Cao Jianhua; Sui Yan; Dong Liang; Zhang Jianchuan; Wang Shibo; Hua Ruimao; (44 pag.)CN107722062; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 138647-49-1, 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. 138647-49-1, name is tert-Butyl 4-(((trifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate. A new synthetic method of this compound is introduced below.

To a mixture of tert-butyl4-(((trifluoromethyl)sulfonyl)oxy)-3 ,6-dihydropyridine-1(2H)-carboxylate (5.6 g, 16.8 mmol), Et3N (4.7 ml, 33.0 mmol) in DMF (69 ml) andMeOH (52 ml) was added PPh3 (0.2 g, 1.0 mmol) and Pd(OAc)2 (0.1 g, 0.5 mmol) at RT under nitrogen followed by stirring under CO atmosphere for 12 h. The reaction mixture was concentrated under reduced pressure. The crude residue was purified by column chromatography to give 2.0 g of the title compound as a greenish liquid. 1H-NMR (400MHz; DMSO-d6): oe 6.85 (d, 1H), 4.00 (t, 2H), 3.67 (s, 3H), 3.42 (d, 2H), 2.25 (t, 2H),1.41 (s, 9H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,138647-49-1, tert-Butyl 4-(((trifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ORION CORPORATION; DIN BELLE, David; MAeKELAe, Mikko; PASSINIEMI, Mikko; PIETIKAeINEN, Pekka; RUMMAKKO, Petteri; TIAINEN, Eija; VAISMAA, Matti; WOHLFAHRT, Gerd; (254 pag.)WO2018/115591; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 36953-37-4, 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. 36953-37-4, name is 4-Bromopyridin-2(1H)-one, molecular formula is C5H4BrNO, 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 sodium 2-chloro-2,2-difluoroacetate (12.38 g, 81 mmol) in MeCN (400 mL) was added 4-bromopyridin-2(1H)-one (10.09 g, 58 mmol) and the reaction was refluxed for 20 h. The mixture was filtered and the solid purified by chromatography on silica gel (80 g column, 0-10% EtOAc/isohexane) to afford the title compound (6.75 g, 51%) as a clear colourless liquid.1H NMR (DMSO-d6) d 8.10 (d, J = 5.5 Hz, 1H), 7.86-7.52 (m, 2H), 7.49 (d, J = 1.6 Hz, 1H).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 36953-37-4, 4-Bromopyridin-2(1H)-one.

Reference:
Patent; INFLAZOME LIMITED; MILLER, David; MACLEOD, Angus; THOM, Stephen; MCPHERSON, Christopher G.; ALANINE, Thomas; CARRILLO ARREGUI, Jokin; CIANA, Claire-Lise; SHANNON, Jonathan; VAN WILTENBURG, Jimmy; DEN HARTOG, Jacobus Antonius Joseph; (603 pag.)WO2019/211463; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1221171-70-5 ,Some common heterocyclic compound, 1221171-70-5, molecular formula is C6H3ClF3NO, 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 cooled solution of 2-chloro-6-(trifluoromethoxy)pyridine (0.3 g, 1.51 mmol) in anhydrous THF (2 ml.) was added LDA (2M in THF, 0.9 ml_, 1 .82 mmol) dropwise over 5 min and the resulting solution was stirred for 2 h at -78C. Iodine (0.5 g, 1 .97 mmol) in anhydrous TFIF (1 ml.) was then added dropwise over 5 min at -78C and stirred for an hour at same temperature. The reaction mixture was then quenched with saturated aq.NFUCI solution (5 ml_). Crude was extracted with EtOAc (10 mL X 2) and combined organic phases were washed with Na2S2C>3 (2M, 10 mL), dried over sodium sulphate, evaporated under reduced pressure to afford a title compound as colourless liquid (0.30g, 61 .07 %), Rf = 0.6 (05% EtOAc in n-Hexane); 1H NMR (300 MHz, Chloroform-d) d 8.09 (d, J = 8.0 Hz, 1 H), 7.02 (d, J = 8.2 Hz, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1221171-70-5, its application will become more common.

Reference:
Patent; NOVARTIS AG; JIRICEK, Jan; NG, Shuyi Pearly; RAO, Srinivasa P S; (126 pag.)WO2019/244049; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1032943-43-3, 4-Bromo-1H-pyrazolo[3,4-c]pyridine, 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, Safety of 4-Bromo-1H-pyrazolo[3,4-c]pyridine, blongs to pyridine-derivatives compound. Safety of 4-Bromo-1H-pyrazolo[3,4-c]pyridine

To a stirred solution of 4-bromo-1H-pyrazolo[3,4-c]pyridine (0.320 g, 1.62 mmol) inDMF (10 mL)were addedZn(CN)2(0.190 g, 1.62 mmol) andZnCl2(0.110 g, 0.808 mmol). The resulting reaction mixture was degassed with nitrogen for 5 minutes and tetrakis(triphenylphosphine)palladium(0) (0.373 g, 0.323 mmol) was added and again degassed with nitrogen for 5 minutes. The reaction mixture was heated in a sealed tube at100 C for 10 h. The reaction mixture was cooled and concentrated under reduced pressure, diluted with water (40 mL) and extracted with EtOAc (2 x 20 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by CombiFlash (Redisep-24 g, 70 % EtOAc/n-hexanes), to obtain Intermediate 1-10 (0.14 g, 60 %). ?HNIVIR (400 MHz, DMSO-d6) ppm 8.50 (s, 1 H), 8.75 (s, 1 H), 9.38 (s, 1 H), 14.32 (br, s,1 H). LCMS (methodE), retention time 0.647 mi [M+H] 145.0.

The synthetic route of 1032943-43-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GUNAGA, Prashantha; RICHTER, Jeremy; YADAV, Navnath Dnyanoba; PANDA, Manoranjan; GODESI, Sreenivasulu; (132 pag.)WO2017/184662; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem