Category: pyridine-derivatives

Reference of 1235036-15-3, 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 1235036-15-3, name is tert-Butyl 3-bromo-6-chloropicolinate. This compound has unique chemical properties. The synthetic route is as follows.

Cs2CO3 (4.1 g, 12.6 mmol) and 4A sieves were dried under high vacuum at 1500C for 6 to 10 hours before the start of the reaction. After cooling to room temperature, compound 94A (0.736g, 2.53 mmol) and compound IB (1.62 g, 3 mmol) were transferred to the reaction vessel and the atmosphere was purged with nitrogen. 12 mL of anhydrous DMA were then added and the reaction was stirred at 1200C for 12 hours. The cooled reaction mixture was then diluted with ethyl acetate and 10% citric acid. The organic phase was washed three times with citric acid, once with water and brine, and dried over Na2SO4. Concentration afforded an orange film/foam. Purification on Flash Master (SiO2, ethyl acetate/petroleum ether 0: 100 to 40:60) afforded a white solid (1.15 g, 80 % yield): 1H NMR (300 MHz, DMSO-d6) delta ppm 12.84 (1 H, s), 8.03 (1 H, d), 7.77 (2 H, m), 7.58 (1 H, d), 7.40 (4 H, m), 6.86 (1 H, d), 4.92 (2 H, s), 3.78 (2 H, t), 3.01 (2 H, t), 1.34 (9 H, s).

According to the analysis of related databases, 1235036-15-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; THE WALTER AND ELIZA HALL INSTITUTE OF MEDICAL RESEARCH; ABBOTT LABORATORIES; BAELL, Jonathon, Bayldon; BUI, Chinh, Thien; COLMAN, Peter; CZABOTAR, Peter; DUDLEY, Danette, A.; FAIRBROTHER, Wayne, J.; FLYGARE, John, A.; LASSENE, Guillaume, Laurent; NDUBAKU, Chudi; NIKOLAKOPOULOS, George; SLEEBS, Brad, Edmund; SMITH, Brian, John; WATSON, Keith, Geoffrey; ELMORE, Steven, W.; HASVOLD, Lisa, A.; PETROS, Andrew, M.; SOUERS, Andrew, J.; TAO, Zhi-Fu; WANG, Le; WANG, Xilu; DESHAYES, Kurt; WO2010/80503; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 886365-46-4, Adding some certain compound to certain chemical reactions, such as: 886365-46-4, name is 5-Chloro-3-methylpyridine-2-carboxylic acid,molecular formula is C7H6ClNO2, 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 886365-46-4.

d) 5-Chloro-3-methylpicolinic acid (30 mg, 0.16 mmol) and N-(3-tert-butylphenyl)-2-phenylpiperidine-3-carboxamide (50 mg, 0.15 mmol, prepared in step c above) were dissolved in anhydrous DMF (1 mL). N,N-Diisopropylethylamine (0.15 mL) was added at room temperature followed by HCTU (67 mg, 0.16 mmol). After stirring 2 h at ambient temperature, LC-MS and TLC indicated the completion of the reaction. The reaction mixture was diluted with EtOAc (50 mL) and washed with 1 N HCl (20 mL), saturated NaHCO3 (30 mL), and brine (30 mL) and the resulting solution was concentrated under reduced pressure.The residue was purified by preparative HPLC (20?95% gradient of MeCN-H2O with 0.1% TFA) and the pure fractions were lyophilized to afford the title compound (50 mg, 67% yield). HPLC retention time=2.88 minutes. 1H NMR (400 MHz, CDCl3) delta 8.42 (d, 1H, J=0.8 Hz), 7.97 (br, 1H), 7.59 (d, 1H, J=0.8 Hz), 7.56 (d, 1H, J=7.6 Hz), 7.34 (m, 3H), 7.20 (m, 3H), 7.10 (d, 1H, J=7.6 Hz), 6.61 (two sets of br, 1H), 3.12 (two sets of m, 2H), 2.94 (three sets of m, 1H), 2.36 (s, 3H), 2.20 (two sets of br, 2H), 1.74 (br complex, 2H), 1.29 (s, 9H). MS: (ES) m/z 490.2 (M+H+).

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. 886365-46-4, 5-Chloro-3-methylpyridine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ChemoCentryx, Inc.; US2010/160320; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 53554-20-4, name is 6-Amino-2-chloronicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 6-Amino-2-chloronicotinonitrile

6-Amino-2-chloronicotinonitrile (250 mg, 1.628 mmol), 1- (methylsulfonyl)piperazine, HC1 (1307 mg, 6.51 rnmo]) and potassium carbonate (675 mg, 4.88 mmol) were suspended in DMA (5426 m). The reaction mixture was heated to 105 C overnight, cooled to rt and stirred for 72 h. The reaction ws decanted into a separatory funnel containing EtOAc and H20, rinsing the residual K2CO3 with EtOAc. The aqueous layer was extracted with EtOAc (2X) and the combined organics were washed with 10% LiCl solution before drying (MgS04) and concentrating to a cream solid to afford the titled product (461 mg, 85% purity, 86% yield). This material was used as is in the subsequent reactions. 1H NMR (4QQMHz, DMSO-d6) d 7.52 (d,.1 8.4 Hz, 1 1 1). 6 83 (br s, 2H), 6.46 (d, 1=8.7 Hz, 1H), 5.99 (d, J=8.4 Hz, 1H), 3.68 – 3.54 (m, 4H), 3.27 – 3.12 (m, 4H), 2.92 (s, 3H); LC/MS [M+H] = 282.2; LC RT 0.63 min; (Column: BEH 08 2.1 x 50mm; Mobile Phase A: water with 0.05% TFA; Mobile Phase B: acetonitrile with 0.05% TFA; Temperature: 50 C; Gradient: 2-98% B over 1.7 min; Flow: 0.8 mL/min).

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, 53554-20-4, 6-Amino-2-chloronicotinonitrile.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; TARBY, Christine M.; NORRIS, Derek J.; LO, Julian C.; AHUJA, Vijay T.; SEITZ, Steven P.; GAVAI, Ashvinikumar V.; TOKARSKI, John S.; RAJASAGI, Mohini; WICHROSKI, Michael; BROEKEMA, Matthias; (155 pag.)WO2019/213340; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 59105-50-9, (5-Bromopyridin-3-yl)(phenyl)methanone, 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, SDS of cas: 59105-50-9, blongs to pyridine-derivatives compound. SDS of cas: 59105-50-9

General procedure: Pd(PPh3)4 (17.3 mg, 0.015 mmol) was added to a solution of 3-benzoy-5-bromo pyridine(130.1 mg, 0.5 mmol) and aryl boronic acid (0.6 mmol) in MeOH (0.2 mL), toluene (0.8 mL),and 2 M Na2CO3 (0.2mL) under N2. The mixture was heated to 75 C for 2 h, and then cooledto room temperature and concentrated under reduced pressure. Water was added to theresidue and the aq. phase was extracted with DCM (3 × 5 mL). The combined organic layerswere washed with brine, dried over Na2SO4, and evaporated to obtain the crude product.Purification by column chromatography on silica gel afforded the desired product.

The synthetic route of 59105-50-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fu, Yun; Sun, Jian; Molecules; vol. 24; 3; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 63996-36-1, 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. 63996-36-1, name is 2-(4-Bromophenyl)pyridine. A new synthetic method of this compound is introduced below.

A solution of 2-bromopyridine (2.0 g) in anhydrous THF (50 ml) was cooled at -78 C in a nitrogen atmosphere, and a solution of tert-butyl lithium in pentane (1.64M, 15.0 ml) was added dropwise. The mixture was stirred for 10 minutes, and a 1M solution of zinc chloride in ether was dropwise added over 10 minutes. After the mixture was allowed to worm to room temperature over 2 hours, a solution of Pd(PPh3)4 (71 mg) and 1-bromo-4-iodobenzene (3.56 g) in anhydrous THF (20 ml) was added, and the mixture was stirred at room temperature for 3 days. To the reaction was added a 10% aqueous ammonia, and the mixture was extracted with ethyl acetate. The ethyl acetate solution was washed with saturated brine, and dried over magnesium sulfate, followed by evaporating the solvent. The residue was purified by silica gel chromatography (70 g, hexane-ethyl acetate = 4: 1) to give 2.37 g of 2-(4-bromophenyl]pyridine (79.9%). To the aliquot of 2-(4-bromophenyl]pyridine (702 mg) were added 3-thiopheneboronic acid (460 mg), Pd(PPh3)4 (104 mg), sodium carbonate (2M, 3.6 ml), and DME (6ml), and the mixture was heated at reflux for 2 hours. After cooling, water was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel chromatography (40 g, hexane-ethyl acetate = 4: 1) to give crude materials, which were recrystallized from ethyl acetate giving 457 mg of the intended compound (64.3%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,63996-36-1, 2-(4-Bromophenyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; SHIONOGI & CO., LTD.; EP1426046; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1198103-43-3, (6-(Difluoromethoxy)pyridin-3-yl)methanamine, 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, HPLC of Formula: C7H8F2N2O, blongs to pyridine-derivatives compound. HPLC of Formula: C7H8F2N2O

Phenyl formate (0.17 mL, 1.5 mmol) was added to a solution of (6- (difluoromethoxy)pyridin-3-yl)methylamine (0.261 g, 1.50 mmol) in dry dichloromethane (5 mL). The mixture was stirred at room temperature for 18 hours then the volatiles were removed in vacuo. The crude residue was purified by silica gel column chromatography using dichloromethane : methanol = 100:0 to 95:5 as gradient affording the title compound as white solid, 250 mg (82 %). 1H NMR (400 MHz, CDCl3) delta (ppm) 8.29 (s, 1 H) 8.12 (s, 1 H) 7.72 (d, 1 H) 7.45 (t, 1 H) 6.89 (d, 1 H) 5.81 (m, 1 H) 4.48 (d, 2 H). 19F NMR (400 MHz, CDCl3) delta (ppm) -89.30 and -89.49. MS (ESI) m/z 202 [M+H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1198103-43-3, (6-(Difluoromethoxy)pyridin-3-yl)methanamine, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; WO2009/145720; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 709652-82-4, 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. 709652-82-4, name is 2-Amino-5-bromonicotinonitrile, molecular formula is C6H4BrN3, 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.

Imidodicarbonic acid, 2-[5-bromo-3-(cyano)-2-pyridinyl]-, 1 ,3-bis(1 , 1 -dimethylethyl) ester To 2-amino-5-bromonicotinonitrile (0.785 g, 3.96 mmol), triethylamine (0.553 mL, 3.96 mmol) and 4-dimethylaminoyridine (20 mg, 0.164 mmol) in CH2CI2 (25 mL) was added di-ferf-butyl- dicarbonate (2.16 g, 9.91 mmol) and the resulting mixture stirred at room temperature for 18h. Evaporated to dryness in vacuo and triturated in heptane (25 mL) for 72h. The resulting precipitate was filtered and washed with heptane (10 mL) to give imidodicarbonic acid, 2-[5- bromo-3-(cyano)-2-pyridinyl]-, 1 ,3-bis(1 , 1-dimethylethyl) ester as a beige solid (1.1 g, 70% yield). 1H N MR (400 Mhz, CDCI3, 298K) 1 .51 (s, 181-1) 8.16 (d, 1 1-1) 8.77 (d, 1 H). LCMS: [M+H]+=398/400.1 , Rt (4)= 1.43 min.

According to the analysis of related databases, 709652-82-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; COOKE, Nigel Graham; FERNANDES GOMES DOS SANTOS, Paulo; GRAVELEAU, Nadege; HEBACH, Christina; HOeGENAUER, Klemens; HOLLINGWORTH, Gregory; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; STOWASSER, Frank; STRANG, Ross; TUFILLI, Nicola; VON MATT, Anette; WOLF, Romain; ZECRI, Frederic; WO2012/4299; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1206978-11-1, Adding some certain compound to certain chemical reactions, such as: 1206978-11-1, name is 2-Bromo-3-(trifluoromethoxy)pyridine,molecular formula is C6H3BrF3NO, 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 1206978-11-1.

A microwave vial was charged with (iS,25)-l-A-(6-fluoro-l,3-beiizothiazol-2- yl)cyclopentane-l,2-di amine hydrochloride (Intermediate 1; 172 mg, 0.60 mmol), molybdenum hexacarbonyl (79 mg, 0.30 mmol), tri-tert-butylphosphonium (0587) tetrafiuoroborate (5 mg, 0.018 mmol), 2-bromo-3-(trifluoromethoxy)pyridine (145 mg, 0.60 mmol), Herrmanns Catalyst (6 mg, 6.41 muetaiotaomicron) and DBU (150 mu, 0.998 mmol) in dry 1,4-dioxane (2.4 ml). The reaction was subjected to microwave irradiation at 125 C for 25 minutes then partitioned between ethyl acetate and water. The organics were washed with water and brine, filtered through a hydrophobic frit and concentrated in vacuo. The crude material was purified by column chromatography (silica, 0 – 100% ethyl acetate / petrol then 0 – 30% methanol /’ ethyl acetate) then further purified by reverse phase preparative HPLC (eluted with acetonitriie / water containing 0.1 % ammonia) to afford the title compound. (0588) 1H NMR (400 MHz, DMSO-6) delta ppm 1.50 – 1.64 (m, 2 H), 1.68 – 1.80 (m, 2 1 1 }.. 2.07 – 2.21 (m, 2 H), 4.13 – 4.23 (m, 1 H), 4.23 – 4.33 (m, 1 H), 6.97 – 7.10 (m, 1 H), 7.26 – 7.37 (m, 1 H), 7.52 – 7.62 (m, 1 H), 7.64 – 7.74 (m, 1 H), 7.90 – 8.03 (m, 1 H), 8.14 – 8.23 (m, 1 H), 8.55 – 8.69 (m, 1 H), 8.92 – 9.02 (m, 1 H) MS ES?: 441

According to the analysis of related databases, 1206978-11-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA CAMBRIDGE LIMITED; TAKEDA PHARMACEUTICAL COMPANY LIMITED; FIELDHOUSE, Charlotte; GLEN, Angela; FUJIMOTO, Tatsuhiko; ROBINSON, John Stephen; WO2015/124934; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 120739-77-7, 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 120739-77-7, name is N-((6-Chloropyridin-3-yl)methyl)ethanamine. This compound has unique chemical properties. The synthetic route is as follows.

1200 kg of dichloromethane was introduced into a 2000 L reactor, and 171 kg (1 kmol) of N-ethyl-2-chloro-5-pyridinemethylamine was added thereto with stirring, 60 L of ion exchange resin 201×7, and the mixture was cooled to an internal temperature of -10 C, and added dropwise. A solution of 157 kg (1.1 kmol) of 1-dichloro-2-nitroethylene and 320 kg of dichloromethane was added dropwise over 3 hours to control the internal temperature below 0 C. After the dropwise addition, the reaction was kept at 0 C for 3 hours. After the reaction is completed, a solution containing the compound (II) is obtained. The solution was further cooled to an internal temperature of -10 C, and slowly introduced into a methylamine gas of 46.5 kg, (1.5 kmol), controlled internal temperature of 0 C or less, and a calculated amount of monomethylamine gas was passed for 3 hours, and the temperature was maintained at 0 C. 3 hours. After completion, filtration, washing the ion exchange resin with dichloromethane, the filtrate is concentrated to dryness, adding 280 kg of ethyl acetate, stirring and crystallization at room temperature for 1 hour, then cooling to 0 C, stirring and crystallization for 3 hours, centrifuging the feed, drying to obtain the acetamid The amine was 252.3 kg, the purity was 99% or more, and the yield was 93%

According to the analysis of related databases, 120739-77-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Jinjing Chemical Co., Ltd.; Chen Xuejun; Ma Jun; Tang Songqing; (6 pag.)CN108822025; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 161117-83-5, tert-Butyl (2-methoxypyridin-3-yl)carbamate, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

4.48 g (20 mmol) of the compound obtained in the preceding step in solution in 100 ml of diethyl ether and 9.05 ml (60 mmol) of tetramethylethylene-diamine are placed in a reactor, protected from moisture, and under a nitrogen atmosphere. After having cooled the solution to -70 C., 37.5 ml (60 mmol) of n-butyllithium in hexane (1.6 M) are added dropwise.. The reaction medium is stirred for 2 hours at -10 C. and then 14.1 g (60 mmol) of dihexyl sulfide are added dropwise at -70 C. After stirring the solution for 12 hours at room temperature, the reaction medium is taken up in water and extracted with diethyl ether.. The organic phase is washed with hydrochloric acid (0.1 M) and then with water until a PH of the washings equal to 7 is obtained, and then finally dried over sodium sulfate.. After evaporation of the solvent, an oil is obtained which is chromatographed on a silica gel (eluent ethyl acetate-hexane: 1-5).. After evaporation of the solvent, 5.6 g of an oil is obtained which crystallizes, that is to say a yield of 82.3%.. Its melting point is between 72 and 74 C. TLC: (MERCK “Kieselgel 60” silica gel; AcOEt-hexane: 1-3); Rf=0.3 I.R.: upsilon NH=3171, CO=1720; NMR: (CDCl3): 0.85 (t, 3H); 1.3 (m, 4H); 1.45 (m, 11H); 1.7-1.8 (m, 2H); 3.0 (t, 2H); 4.25 (s, 3H); 6.7 (d, 1H, J=6.8 Hz); 7.85 (d, 1H, J=6.8 Hz).

The synthetic route of 161117-83-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Patent GmbH; US6339097; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem