Pyridine-derivatives

Synthetic Route of 4548-45-2 , The common heterocyclic compound, 4548-45-2, name is 2-Chloro-5-nitropyridine, molecular formula is C5H3ClN2O2, 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 tert-butyl piperazine-1-carboxylate (64 g, 346 mmol) in 600 ml. of THF at O0C was added NaH (16.4 g, 409 mmol, 60% in mineral oil) portionwise. The reaction mixture was stirred for 15 min and 2-chloro-5-nitropyridine (50 g, 314 mmol) was added. The reaction mixture was allowed to warm to rt and then heated to 5O0C for 4 h. The reaction was quenched by water (30 ml.) and extracted with DCM (1.5 Lx 3). The combined organic layers were dried over Na2SO4 and the solvent was removed under reduced pressure. The residue was subjected to wash with petroleum ether to give the desired product of Step A (80 g, yield 83%). 1H NMR (CDCI3, 400 MHz) delta 8.95 (d, J = 2.4 Hz, 1 H), 8.24 (d, J = 12 Hz, 1 H), 6.92 (d, J = 6.0 Hz, 1 H), 3.75 (s, 4 H), 3.44 (s, 4H), and 1.41 (s, 9 H).

The synthetic route of 4548-45-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/32667; (2009); 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. 52718-95-3, name is Methyl 2-bromonicotinate. A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 2-bromonicotinate

Step 1) Methyl 2-[(4-Hydroxymethyl)phenyl]-3-pyridinecarboxylate To a stirred solution of methyl 2-bromo-3-pyridinecarboxylate (3.45 g, 14.39 mmol) and 4-(trimethylstannyl)benzyl alcohol (3.90 g, 14.39 mmol), prepared as described in Step 1 of Example 3, in DMF (25 mL) was added bis(acetonitrile)palladium dichloride (0.19 g, 0.72 mmol) and CuI (0.27 g, 1.44 mmol). After 18 h, bis(triphenylphosphine)palladium dichloride (0.20 g, 0.28 mmol) and CuI (0.11 g, 0.57 mmol) were added and stirring was continued for 2 days at room temperature. The mixture was concentrated, taken up in water, and extracted with EtOAc. The combined extracts were washed with brine, dried, and concentrated. Purification by flash chromatography (50% EtOAc/hexane) gave 277 mg (8%) of product as a yellow oil. 1 H NMR (CDCl3) delta 3.69 (s, 3H), 4.69 (s, 2H), 7.35 (m, 1H), 7.38 (d, J=8.2 Hz, 2H), 7.49 (d, J=8.2 Hz, 2H), 8.08 (dd, J=7.9, 1.8 Hz, 1H), 8.75 (m, 1H).

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, 52718-95-3, Methyl 2-bromonicotinate.

Reference:
Patent; American Home Products Corporation; US5283242; (1994); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 7205-46-1, 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. 7205-46-1, name is 6-Chloro-1-methyl-1H-imidazo[4,5-c]pyridine, molecular formula is C7H6ClN3, 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 mixture of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.08 g), 6-chloro-l-methyl- lH-imidazo[4,5-c]pyridine (0.23 g, 0.0014 mol), 3-amino-4-ethyl-N,N-dimethylbenzamide (0.27 g, 0.0014 mol) and sodium tert-butoxide (0.20 g, 0.0021 mol) in 1,4-dioxane (15 mL) was stirred under N2 for 20 min. Tris(dibenzylideneacetone)dipalladium(0) (0.06 g) was added and the mixture was stirred at 100C for 7 h. The reaction mixture was concentrated in vacuo and the residue was treated with water and extracted into EtOAc. The organics were washed with brine, dried (MgSO i) and concentrated in vacuo to give the desired compound. For analytical purpose, a 60 mg sample was further purified by preparative HPLC to give the desired compound. [00324] NMR delta (ppm)(CHCl3-d): 8.69 (1 H, d, ArH), 7.71 (1 H, s, ArH), 7.52 (1 H, d, ArH), 7.32 (1 H, m, ArH), 7.16 (1 H, dd, ArH), 6.63 (1 H, d, ArH), 6.36 (1 H, s, NH), 3.68 (3 H, s, CH3), 3.09 (3 H, s, CH3), 3.03 (3 H, s, CH3), 2.69 (2 H, q, CH2), 1.24 (3 H, t, CH3). [00325] LCMS (lOcm ESCI Formic MeCN) tR 2.21 (min) m/z 324 (MH+).

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 7205-46-1, 6-Chloro-1-methyl-1H-imidazo[4,5-c]pyridine.

Reference:
Patent; GALAPAGOS NV; MENET, Christel; SCHMITT, Benoit; GENEY, Raphael; DOYLE, Kevin; PEACH, Joanne; PALMER, Nicholas; JONES, Graham; HARDY, David; DUFFY, James; WO2013/117649; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 74976-31-1, 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 74976-31-1, name is 6-Chloro-1H-pyrrolo[3,2-c]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

Into a 100 mL 3-necked round-bottom flask was added a solution of 6-chloro- lH-pyrrolo [3, 2- c]pyridine (1.00 g, 6.55 mmol) in N,N-dimethylformamide (10 mL), potassium hydroxide (1.40 g, 24.9 mmol). The reaction mixture was stirred for 20 min at room temperature, then I2 (1.66 g, 6.54 mmol, 1.00) was added to the solution. The reaction mixture was stirred for additional 30 min at room temperature. The reaction mixture was diluted with H20 (50 mL) and the solids were collected by filtration. The solids were dried under reduced pressure overnight to afford 6-chloro- 3-iodo-lH-pyrrolo[3,2-c]pyridine (1.70 g, 93.0%) as a yellow solid. LCMS (ESI): RT (min) = 1.321, [M+H]+ = 279, method = N.

According to the analysis of related databases, 74976-31-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; BRYAN, Marian C.; CHAN, Bryan; HANAN, Emily; HEFFRON, Timothy; PURKEY, Hans; ELLIOTT, Richard Leonard; HEALD, Robert; KNIGHT, Jamie; LAINCHBURY, Michael; SEWARD, Eileen M.; WO2014/81718; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 67515-76-8, Adding some certain compound to certain chemical reactions, such as: 67515-76-8, name is Methyl 5-aminopicolinate,molecular formula is C7H8N2O2, 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 67515-76-8.

Reference Example 17 Methyl 5-(tert-butoxycarbonylamino)-6-iodopyridine-2-carboxylate A mixture of methyl 5-aminopyridine-2-carboxylate (2.92 g), iodine (3.9 g) and sodium periodate (1.64 g) in N,N-dimethylformamide (24 mL) was stirred at 60C for 2 days. The reaction mixture was cooled to room temperature. To the reaction mixture was added 10% aqueous sodium sulfite solution, and the resulting mixture was stirred for 10 minutes. The crystals were collected by filtration. The collected crystals were washed with water, and dried under reduced pressure to give methyl 5-amino-6-iodopyridine-2-carboxylate (3.26 g). To sodium hexamethyldisilazide (1.03 mol/L tetrahydrofuran solution, 7.68 mL) was added a solution of methyl 5-amino-6-iodopyridine-2-carboxylate (1 g) in tetrahydrofuran (5 mL) in a dropwise manner at -14C, and the mixture was stirred at the same temperature for 10 minutes. To the mixture was added a solution of di(tert-butyl)dicarbonate (0.82 g) in tetrahydrofuran (3 mL) in a dropwise manner, and the mixture was stirred at the same temperature for 30 minutes. To the reaction mixture was added 1 mol/L hydrochloric acid (13.6 mL), and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. To the residue were added 2-propanol (2.8 mL) and water (3.4 mL), and the mixture was stirred at 80C for 30 minutes, and then stirred at room temperature for 30 minutes. The crystals were collected by filtration. The collected crystals were washed with a mixed solvent (2-propanol/water = 5/6), and dried under reduced pressure to give the title compound (0.82 g).

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. 67515-76-8, Methyl 5-aminopicolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; EP2143724; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1822-51-1, Adding some certain compound to certain chemical reactions, such as: 1822-51-1, name is 4-(Chloromethyl)pyridine hydrochloride,molecular formula is C6H7Cl2N, 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 1822-51-1.

A mixture of 4-hydroxylbenzaldehyde (2a) (1.2 g, 10 mmol), 4-(chloromethyl)pyridine hydrochloride (1.6 g, 10 mmol) and K2CO3 (4.2 g, 30 mmol) in dry DMF (12 mL) was stirred at 80 for 7 h. The cooled mixture was extracted with EtOAc (100 mL). The organic layer was washed with brine (2 × 100 mL) , dried (MgSO4) and concentrated to dryness. Yield = 1.3 g (61 %), tan crystals, recrystallised with methanol. m. p. = 102 – 104 (Lit. m. p. 57 – 58 ). TLC: petroleum ether-EtOAc 1: 3 v/v, Rf = 0.24 .1H NMR (DMSO-d6): delta 9.89 (s, 1H, CHO), 8.60 (dd, J = 1.6, 4.5 Hz, 2H, Ar), 7.91 (m, 2H, Ar), 7.47 (d, J = 6.3 Hz, 2H, Ar), 7.22 (dd, J = 1.8, 7Hz, 2H, Ar), 5.33 (s, 2H, CH2).

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. 1822-51-1, 4-(Chloromethyl)pyridine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Taban, Ismail M.; Zhu, Jinge; DeLuca, Hector F.; Simons, Claire; Bioorganic and Medicinal Chemistry; vol. 25; 20; (2017); p. 5629 – 5636;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 884494-37-5, 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 884494-37-5, name is 2-Bromo-3-fluoro-4-picoline. This compound has unique chemical properties. The synthetic route is as follows.

[00415] Intermediate 44A. Methyl l-(3-fluoro-4-methylpyridin-2-yl)-lH-imidazole-4- carboxylate: A suspension of methyl lH-imidazole-4-carboxylate (83 mg, 0.658 mmol), 2-bromo-3-fluoro-4-methylpyridine (200 mg, 1.053 mmol), copper (I) iodide (125 mg, 0.658 mmol) and potassium carbonate (546 mg, 3.95 mmol) in DMSO (2 mL) was heated at 120 for 90 min under microwave conditions. The reaction mixture was quenched with H20, and the solid was suspended in EtOAc and MeOH. The combined organic layer was concentrated in vacuo, yielding oily residue, which was purified by reverse phase HPLC to give the desired product (5 mg, 3%). MS(ESI) m/z: 236.1 (M+H)+.

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 884494-37-5, 2-Bromo-3-fluoro-4-picoline.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PINTO, Donald J.; CORTE, James R.; GILLIGAN, Paul J.; FANG, Tianan; SMITH II, Leon M.; WANG, Yufeng; YANG, Wu; EWING, William R.; WO2013/22818; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 504-24-5, 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. 504-24-5, name is 4-Aminopyridine. A new synthetic method of this compound is introduced below.

(1) Bromination reaction:In a 100 ml three-necked flask, 3.76 g (0.04 mol)4-aminopyridineAnd 0.04 g of azobisisobutyronitrile were dissolved in 36 ml of carbon tetrachloride,14.95g (0.084mol) of N-bromosuccinimide was added portionwise at 25 C, the reaction was carried out for 20h,After the liquid-phase central control monitored the conversion of 4-aminopyridine and intermediate 3-bromo-4-aminopyridine into the target product 3,5-dibromo-4-aminopyridine,The reaction mixture was cooled to room temperature with stirring, poured into 50ml carbon tetrachloride and stirred, filtered, the filter cake was washed twice with 2 × 30ml carbon tetrachloride, the filtrate was washed once with aqueous sodium bicarbonate solution, saturated salt Water once, spin-dried to remove carbon tetrachloride, and then recrystallized from petroleum ether,9.28 g of a white solid was obtained,Namely 3,5-dibromo-4-aminopyridine,Yield 92.10%

At the same time, in my other blogs, there are other synthetic methods of this type of compound,504-24-5, 4-Aminopyridine, and friends who are interested can also refer to it.

Reference:
Patent; Shanghai Wohua Chemical Co., Ltd.; Hu Yadong; Yang Benmei; (5 pag.)CN106957259; (2017); 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 74420-15-8, name is 3-Bromo-1H-pyrrolo[2,3-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 3-Bromo-1H-pyrrolo[2,3-b]pyridine

To a mixture of tert-butyl piperazine- 1-carboxylate (224 mg, 1.2 equiv.), 3-bromo-lH- pyrrolo[2,3-£]pyridine (197 mg, 1 equiv.), RuPhos (9.3 mg, 0.02 equiv.) and Ruphos Pd Gl, MTBE adduct (16.3 mg, 0.02 equiv.) in THF (2 mL), under argon atmosphere, a 1.3 M THF solution of LiHMDS (1.92 mL, 2.5 equiv.) was added. The resulting mixture was purged with argon for 5 min, and was then sealed in a vial and heated at 70 C for 3 h. The reaction mixture was cooled to RT, quenched by an addition of 1 M HC1 (1.5 mL), diluted with EtOAc and poured into a sat. solution of sodium bicarbonate. After extracting with 3 portions of EtO Ac, combined organic extracts were dried, and the solvent was removed in vacuo. The obtained residue was purified by flash chromatography on silica gel (eluting with a cyclohexane/EtOAc gradient, 0-100 % of EtO Ac) to afford the expected product (165 mg). LCMS: MW (calc’d): 302.4; MS (ES+, m/z): 303.2 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 74420-15-8.

Reference:
Patent; E-THERAPEUTICS PLC; JURKOVIC, Mihaela; LANDEK, Ivana Ozimec; POLJAK, Tanja; RO?CIC, Maja; STUBBERFIELD, Colin; VADLAMUDI, Srinivasamurthy; (228 pag.)WO2019/43372; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6959-47-3 , The common heterocyclic compound, 6959-47-3, name is 2-(Chloromethyl)pyridine hydrochloride, molecular formula is C6H7Cl2N, 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.

The ligand L3 was prepared by modifying an established method bySong et al. [24]. To a 100 mL round bottom flask, 15 mL of doubledistilled water was added, followed by an addition of 2-chloromethylpyridineHCl (4.96 g, 0.03 mol). Cyclohexylamine (1.73 mL,0.015 mol) was added dropwise to the mixture which was stirred for5 min before adding NaOH pellets (2.4 g, 0.06 mol). The mixture wasfurther stirred for 5 days at room temperature and the product was thenextracted with 3×30 mL portions of CHCl3. The organic layers werecombined and dried over MgSO4, yielding a crude product that waspassed through a silica column and eluted with CHCl3. The off-white crystalline solid obtained was isolated in moderate yield (1.8 g, 43%based on cyclohexylamine). 1H NMR (DMSO): delta 1.1 (m, 2H, CH2-cy),1.3 (q, 2H, J=11.1 Hz, CH2-cy), 1.5 (m, 2H, CH2-cy), 1.7 (m, 2H, CH2-cy), 1.8 (d, 2H, J=12.6 Hz, CH2-cy), 2.4 (m, 1H, CH2-cy), 3.8 (s, 4H,N-CH2-py), 7.2 (ddd, 2H, J=7.6, 3.9, 1.1 Hz, CH-py), 7.5 (d, 2H,J=7.6 Hz, CH-py), 7.7 (ddd, 2H, J=8.6, 7.8, 1.7 Hz, CH-py), 8.4 (d, 2H, J=4.9 Hz, CH-py). 13C NMR (DMSO): delta 24.4 (CH2-cy), 25.6 (CH2-cy), 25.7 (CH2-cy), 28.4 (CH2-cy), 32.9 (CH2-cy), 56.0 (N-CH2-py), 59.3(CH-cy), 121.8 (CH-py), 122.0 (CH-py), 136.3 (CH-py), 148.5 (CH-py),160.8 (C-py). IR numax (cm-1): 2923 (w), 2851 (w), 1587 (w), 1440 (w),1359 (s), 1127 (w), 754 (s), 620 (s). Melting point: 57.3-60.1 C. m/z[M+H]+ (calcd): 282.20 (282.40).

The synthetic route of 6959-47-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chanerika, Revana; Friedrich, Holger B.; Shozi, Mzamo L.; Inorganica Chimica Acta; vol. 495; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem