Category: pyridine-derivatives

Synthetic Route of 866775-18-0, 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. 866775-18-0, name is Methyl 3-amino-6-bromo-5-(trifluoromethyl)picolinate, molecular formula is C8H6BrF3N2O2, 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.

Step 1 : Methyl 3-amino-6-(4-fluorophenyl)-5-(trifluoromethyl)picolinate 3-Amino-6-bromo-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester (Intermediate 3D) (200 mg, 0.669 mmol), 4-fluorophenylboronic acid (94 mg, 0.669 mmol) and 1 , 1 ‘bis(diphenylphosphoshio)ferrocene palladium dichloride (Apollo) were suspended in THF (2 ml) and 1 M Cs2C03 (0.667 ml). The vial was flushed with N2, sealed and heated at 160C for 15 minutes using microwave radiation. The reaction mixture was partitioned between EtOAc (50 ml) and water (50 ml). The organic portion was separated and washed with brine (30 ml), dried over MgS04, filtered and concentrated in vacuo. Purification by chromatography on silica eluting with 0-80% EtOAc in iso-hexane afforded the title compound; LCMS: Rt = 1 .47 mins, [M+H]+ 315.1 ; Method 2minl_C_v002. Step 2: 3-Amino-6-(4-fluorophenyl)-5-(trifluoromethyl)picolinic acid To a stirred solution of methyl 3-amino-6-(4-fluorophenyl)-5-(trifluoromethyl)picolinate (step 1 ) (6.00 mmol) in EtOH (5 ml) was added 2M NaOH (3 ml, 6.00 mmol) and the solution was stirred at RT for 15 minutes. The resulting mixture was diluted with water (10 ml) and the pH was adjusted to pH 6 using 1 M HCI. The mixture was extracted with DCM (2 x 10 ml) and the phases were separated using a phase separating cartridge. The combined organic extracts were concentrated in vacuo and used in the next step without further purification; LCMS: Rt = 1 .42 mins, [M+H]+ 301.1 ; Method 2minl_C_v002. Step 3: 3-Amino-6-(4-fluorophenyl)-N-(1 H-pyrazol-3-yl)-5- (trifluoromethyl)picolinamide A stirred solution of 3-amino-6-(4-fluorophenyl)-5-(trifluoromethyl)picolinic acid (0.167 mmol) in dry NMP (2 ml) was treated with 1 H-pyrazol-3-amine (0.183 mmol). After stirring at RT, triethylamine (0.366 mmol) was added and stirring continued for 5 minutes. HATU (0.183 mmol) was added and the resulting mixture was sealed and heated at 100 C for 1 hour using microwave radiation. The mixture was partitioned between EtOAc (25 ml) and 1 M NaOH (25 ml). The organic portion was separated, washed with water (25 ml), dried over MgS04 and concentrated in vacuo. Purification by mass directed LCMS eluting with TFA/MeCN/water afforded the title compound as a TFA salt. The salt was partitioned between EtOAc (10 ml) and sodium bicarbonate (10 ml). The organic portion was separated, passed through phase separating cartridge and concentrated in vacuo to afford the title compound; LCMS: Rt = 1 .58 mins, [M+H]+ 366.2; Method 2minLC_v002. 1 H NMR (400MHz, DMSO – d6) delta 12.6 (1 H, s), 10.2 (1 H, s), 7.82 (1 H, s), 7.78 (1 H, s), 7.62 (2H, m), 7.3 – 7.4 (4H, m), 6.72 (1 H, s).

According to the analysis of related databases, 866775-18-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; BALA, Kamlesh, Jagdis; BUDD, Emma; EDWARDS, Lee; HOWSHAM, Catherine; LEGRAND, Darren, Mark; TAYLOR, Roger, John; WO2013/38390; (2013); 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. 166266-19-9, name is 5-Iodo-3-methylpyridin-2-amine. A new synthetic method of this compound is introduced below., COA of Formula: C6H7IN2

Step 23.1: 5-iodo-3-methylpyridin-2-ol Sodium nitrite (0.708 g, 10.25 mmol) was added to a mixture of 5-iodo-3-methyl-pyridin-2-ylamine (2 g, 8.55 mmol) and H2SO4 (12 mL) at 0 C. The reaction mixture was stirred 15 min at 60 C., allowed to cool down, and poured onto crushed ice. Boric acid (1.057 g, 17.09 mmol) was added and the solution was quickly heated to 100 C. The reaction mixture was cooled down and neutralized with a saturated aq. NH4OH solution. The suspension was filtered to afford the crude title product (1.67 g, 7.11 mmol, 83% yield) as a brown solid. tR: 2.85 min (HPLC 1); tR: 0.62 min (LC-MS 2); ESI-MS: 236 [M+H]+ (LC-MS 2).

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, 166266-19-9, 5-Iodo-3-methylpyridin-2-amine.

Reference:
Patent; NOVARTIS AG; BLANK, Jutta; BORDAS, Vincent; COTESTA, Simona; GUAGNANO, Vito; RUEEGER, Heinrich; VAUPEL, Andrea; US2014/349990; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 52605-96-6, 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.52605-96-6, name is 2-Chloro-3-methoxypyridine, molecular formula is C6H6ClNO, molecular weight is 143.57, as common compound, the synthetic route is as follows.

1) Preparation of 2-Hydrazino-3-methoxypyridine To 50 ml of a butanol solution of 9.376 g of 2-chloro-3-methoxypyridine were added 16 ml of hydrazine monohydrate and 9.03 g of anhydrous potassium carbonate, and the mixture was heated under reflux for 20 hours. After cooling, the reaction mixture was poured into 200 ml of water and extracted with a mixed solvent of methanol-chloroform (1:9 by volume). The organic layer was washed with a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate. The solvent was removed by evaporation. The residue was subjected to silica gel column chromatography using a mixture of chloroform-methanol (20:1 by volume) as an elude. The fraction containing the desired compound was concentrated to afford 5.952 g of the title compound. 1H-NMR (CDCl3) delta: 3.83 (s, 3H), 6.13 (br, 1H), 6.64 (dd, 1H, J=8, 5 Hz), 6.87 (dd, 1H, J=8, 1 Hz), 7.77 (dd, 1H, J=5, 1 Hz).

The chemical industry reduces the impact on the environment during synthesis 52605-96-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Daiichi Pharmaceutical Co., Ltd.; US6169086; (2001); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 98139-15-2, 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. 98139-15-2, name is 4-Aminopicolinonitrile. A new synthetic method of this compound is introduced below.

Ethyl 4-chlorosulfonyl-3-fluoro-l-methyl-pyrrole-2-carboxylate (1200 mg, 4.45 mmol) was dissolved in dry pyridine (21 mL, 0.98 g/mL, 260.17 mmol). l,l,l-trifluoro-2-methylpropan-2- amine (1131.2 mg, 8.9 mmol) was added and the mixture was stirred at room temperature for 3 hours. The mixture was concentrated in vacuo. The residue was purified by silica gel column chromatography using gradient elution from heptane to EtOAc (100:0 to 0: 100) yielding ethyl 3- fluoro-l-methyl-4-[(2,2,2-trifluoro-l,l-dimethyl-ethyl)sulfamoyl]pyrrole-2-carboxylate (1.15 g) as a beige powder which was used as such in the next step. Ethyl 3-fluoro-l-methyl-4-[(2,2,2- trifluoro- l,l-dimethyl-ethyl)sulfamoyl]pyrrole-2-carboxylate (0.15 g, 0.42 mmol) and (0863) 4-aminopyridine-2-carbonitrile (54.55 mg, 0.46 mmol) were dissolved in THF (4.1 mL) in a tube. The tube was flushed with nitrogen, capped with a septum and stirred at room temperature. To this was added lithium bis(trimethylsilyl)amide (1.04 mL, 1 M, 1.04 mmol) at once using a syringe. The obtained solution was stirred for 3 hours. Then ammonium chloride (aq. / sat. / 10 mL) was added and the layers where separated. Then it was extracted once using ethyl acetate (10 mL). The combined extracts were concentrated in vacuo and purified by silica gel column chromatography using gradient elution from heptane to EtOAc. (100:0 to 0:100). The obtained fractions were concentrated in vacuo and repurified by Prep HPLC (RP SunFire Prep CI 8 OmicronBeta-10muiotaeta,30chi150 mm), mobile phase (0.25% NH4HCO3 solution in water, MeOH). The desired fractions were concentrated under reduced pressure and co-evaporated twice with methanol (2 X 20 mL) and dried in a vacuum oven at 55C for 18 hours yielding compound 188 (45 mg) as a white powder. Method B: Rt: 0.94 min. m/z: 432.1 (M-H)” Exact mass: 433.1. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.39 (s, 6 H), 3.83 (s, 3 H), 7.58 (d, J=4.4 Hz, 1 H), 7.91 (dd, J=5.6, 1.9 Hz, 1 H), 8.21 (d, J=1.8 Hz, 1 H), 8.47 (br. s., 1 H), 8.63 (d, J=5.7 Hz, 1 H), 10.67 (br. s., 1 H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98139-15-2, 4-Aminopicolinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN SCIENCES IRELAND UC; VANDYCK, Koen; HACHE, Geerwin Yvonne Paul; LAST, Stefaan Julien; ROMBOUTS, Geert; VERSCHUEREN, Wim Gaston; RABOISSON, Pierre Jean-Marie Bernard; WO2015/118057; (2015); 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. 135124-71-9, name is 5-(Hydroxymethyl)nicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows. Safety of 5-(Hydroxymethyl)nicotinonitrile

Preparation 68; 5-Chloromethyl-nicotinonitrile; Add thionyl chloride (1mL) to a solution of 5-hydroxymethyl-nicotinonitrile (45mg, 0. 34mmol, lequiv) in anhydr CH2C12 (1mL). After 20min, basify the reaction with satd aq NaHC03 (12 mL). Extract this mixture with Et2O (2x 5mL). Dry the combined organic layers (anhydr MgS04) and rotary evaporate (40C) to yield 4.9mg (9.6%) of 5-chloromethyl-nicotinonitrile as a yellow film. MS (m/z): 152.

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, 135124-71-9, 5-(Hydroxymethyl)nicotinonitrile.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/66126; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 59020-10-9 ,Some common heterocyclic compound, 59020-10-9, molecular formula is C17H31NSn, 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.

34a. 5-(3-Pyridinyl)-6-chloro-3-(1-BOC-2-(S)-pyrrolidinylmethoxy)pyridine To a solution of 5-bromo-6-chloro-3-(1-BOC-2-(S)-pyrrolidinylmethoxy)pyridine (from Example 23a, 500 mg, 1.28 mmol) in toluene (10.0 mL) was added 3-pyridinyltributyltin (564 mg, 1.5 mmol) and tetrakis(triphenylphosphine)palladium(0) (45 mg, 0.039 mmol). After being refluxed overnight, the resulting mixture was cooled to room temperature. Solvent was removed and the residue was chromatographed on a silica gel column, eluding with hexane/EtOAc 2:1 and 1:1 to afford an oil (428 mg, 86%). MS (CI/NH3) m/z 390 (M+H)+. 1H NMR (CDCl3, 300 MHz) delta 1.24-1.67 (m, 2H), 1.44 (s, 9H), 1.86-2.10 (m, 2H), 3.32-3.45 (m, 2H), 3.95-4.27 (m, 3H), 7.28-7.44 (m, 2H), 7.81-7.86 (m, 1H), 8.14-8.17 (m, 1H), 8.65-8.73 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,59020-10-9, its application will become more common.

Reference:
Patent; Abbott Laboratories; US6437138; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 562825-95-0 ,Some common heterocyclic compound, 562825-95-0, molecular formula is C7H9N3O2, 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-amino-3-nitropyridine (2.0 mmol) in DMF (10 mL), NaH (2.2 mmol) was addedslowly, the mixture was stirred at room temperature for 30 min. Then ethyl iodine (2.0 mmol) wasadded slowly into the mixture until the reaction is finished monitored by TLC. Then the solvent wasevaporated and the residue was purified by silica gel chromatography by DCM/MeOH system toafford 4-ethylamino-3-nitropydine.To a solution of 4-ethylamino-3-nitropydine (1.0 mmol) in EtOH (10 mL), 10% Pd/C was added.Then the mixture was reduced by catalytic hydrogenation. Until the completion of the reaction,the Pd/C was filtered and the solvent was evaporated. The product was used in the next step withoutfurther purification.The solution of substituted 4-ethylamino-3-aminopydine (0.5 mmol), benzaldehyde (0.5 mmol)with sodium pyrosulfite (0.5 mmol) was stirred in DMF (8 mL) under 120 C overnight. On completionof the reaction, the solvent was evaporated and the residue was purified by silica gel chromatographyby DCM/MeOH system to afford the final product. If necessary, the crude product could berecrystallized in DCM to afford pure compound [31].

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. 562825-95-0, N-Ethyl-3-nitropyridin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Pan, Liangkun; Hang, Nan; Zhang, Chao; Chen, Yu; Li, Shuchun; Sun, Yang; Li, Zhongjun; Meng, Xiangbao; Molecules; vol. 22; 2; (2017);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 884494-69-3, Adding some certain compound to certain chemical reactions, such as: 884494-69-3, name is 3-Fluoro-2-methoxypyridine,molecular formula is C6H6FNO, 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 884494-69-3.

General procedure: A 3 mL glass vial was equipped with a rubber septum and magnetic stir bar. The vial was brought into a glove box and charged with methyl trifluoromethylsulfonate (MeOTf, 51 muL, 0.46 mmol) by micropipette with polypropylene tip. The vial was sealed and removed from the glove box. A separate 3 mL vial was charged with substrate (68 mg, 0.46 mmol) and was dissolved in PhMe (0.5 mL). The solution of pyridine was added via syringe onto the sealed vial of MeOTf at room temperature. The vial which contained the pyridine was rinsed with PhMe (0.2 mL) and the rinse solution was injected into the reaction vial. The reaction vial was kept at room temperature and stirring was maintained at ca. 400-600 rpm. Over the course of the reaction (2 hr), a precipitate formed. At the end of the reaction, PhMe (2 mL) was added after which stirring was stopped. Any solid or oil was allowed to settle and the solvent was removed by glass pipette. The residue was then rinsed with several portions of hexanes to remove any unreacted starting materials, again removing the solvent by pipette. Residual solvent was then removed in vacuo to provide the title compound (53 mg, 37%).

According to the analysis of related databases, 884494-69-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Topczewski, Joseph J.; Lodge, Alexander M.; Yasapala, Sumana N.; Payne, Maurice K.; Keshavarzi, Pedrom M.; Quinn, Daniel M.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 21; (2013); p. 5786 – 5789;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 56946-65-7 ,Some common heterocyclic compound, 56946-65-7, molecular formula is C8H7Cl2N, 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 2,4-dichloro-6,7-dihydro-5H-cyclopenta[^]pyridine (0.130 g, 0.69 mmol) in dioxane (3 mL) was added tributyl(furan-2-yl)stannane (0.271 g, 0.76 mmol) and tetrakis(triphenylphosphine)palladium (0.039 g, 0.035 mmol). The mixture was purged with nitrogen and then heated to 110 C under sealed conditions for 2 h. After this time, the mixture was diluted with water and extracted with ethyl acetate. The organic layer were dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by column chromatography (silica, hexanes/ethyl acetate) to afford the title compound (0.140 g, 92%) as a white solid. MW = 219.67. ]H NMR (CDC13, 500 MHz) delta 7.52-7.48 (m, 1H), 7.45 (s, 1H), 7.02-6.98 (m, 1H), 6.52-6.48 (m, 1H), 3.10 (t, / = 7.5 Hz, 2H), 2.99 (t, J = 7.5 Hz, 2H), 2.15 (quin, J = 7.5 Hz, 2H); APCI MS m/z 220 [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. 56946-65-7, 2,4-Dichloro-6,7-dihydro-5H-cyclopenta[b]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TETRA DISCOVERY PARTNERS, LLC.; GURNEY, Mark, E.; HAGEN, Timothy, J.; MO, Xuesheng; VELLEKOOP, A.; ROMERO, Donna, L.; CAMPBELL, Robert, F.; WALKER, Joel, R.; ZHU, Lei; WO2014/66659; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 97986-08-8, N,6-dimethylpyridin-2-amine, 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, 97986-08-8, blongs to pyridine-derivatives compound. Safety of N,6-dimethylpyridin-2-amine

Example 11N-[3,5-difmorpholin-4-yl)phenyll-N>-methyl-N>-f6-methylpyridin-2-yl)pyrimidine-2.,4- diamine4-Chloro-N-(3,5-dimorpholin-4-ylphenyl)pyrimidin-2-amine (described in Example 1, 200 mg, 0.53 mmol), 6-methyl-2-methylaminopyridine (98 mg, 0.8 mmol), potassium carbonate (736 mg, 5.3 mmol), Pd2dba3 (16 mg, 0.027 mmol) and Xantphos (31 mg, 0.053 mmol) were mixed in toluene (5 ml). The mixture was degassed with nitrogen and heated in a sealed tube at 1200C for 3 hours. After filtration, the toluene was evaporated and the residue purified on a preparative HPLC-MS system (Column: C18, 5 microns, 19 mm diameter, 100 mm length, elution with a gradient of water and acetonitrile containing 2g/l of ammonium carbonate) to give 55 mg of the title compound (22% yield). NMR Spectrum (500 MHz, DMSOd) 2.45 (s, 3H), 3.01 (m, 8H), 3.51 (s, 3H), 3.70 (m, 8H), 6.10 (s, IH), 6.30 (d, IH), 6.93 (d, 2H), 7.07 (d, IH), 7.23 (d, IH), 7.70 (t, IH), 8.00 (d, IH), 8.92 (s, IH). Mass Spectrum MH+ 462

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,97986-08-8, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/10794; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem