Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 1137-67-3, 2-(Pyridin-3-yl)-1H-benzo[d]imidazole, 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, Formula: C12H9N3, blongs to pyridine-derivatives compound. Formula: C12H9N3

A solution of 2-(3-pyridyl)-1H-benzimidazole, L1, (0.34 g,1.79 mmol) in methanol (4 ml) was added to a solution ofZn(OAc)22H2O (0.39 g, 1.79 mmol) in methanol (6 ml).The mixture was stirred for 24 h at room temperature to give a white precipitate. After the reaction period, the precipitate was filtered off, washed with methanol (3 9 20 mL) and dried to afford complex 1 as a white solid. Yield = 0.39 g (58 %). 1H NMR (400 MHz,DMSO-d6): d(ppm): 13.15 (s, 1H, NH), 9.45 (d, 1H, 3JHH = 7.19 Hz, ArH), 8.76 (d, 1H, 3JHH = 7.29 Hz,ArH), 8.54 (d, 1H, 3JHH = 7.29 Hz, ArH), 7.61 (d, 2H,3JHH = 7.19 Hz, ArH), 7.21 (d, 2H, 3JHH = 7.30 Hz,ArH), 1.80 (s, 6H, CH3). IR m (cm-1): 3074.87 (weak, N-H), 1625 (strong, C=O), 1601 (medium, C=Npy), 1445(weak, ArH). (ESI-MS) m/z (%): 194 (M?-Zn2C8H13O8-L1, 100 %); 314 (M?-ZnC6H13O6L1, 8.0 %), 501 (M?-ZnC7H12O6, 8.2 %), 501(M?-C4H12, 8.2 %). Anal. Calcd.for C16H15N3O4Zn: C, 50.75; H, 3.99; N, 10.00. Found: C,50.60; H, 3.70; N, 9.65.

The synthetic route of 1137-67-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zaca, Thembisile P.; Ojwach, Stephen O.; Akerman, Matthew P.; Transition Metal Chemistry; vol. 41; 6; (2016); p. 663 – 673;,
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. 72141-44-7, name is 4-Chloro-2-methoxypyridine, the common compound, a new synthetic route is introduced below. Quality Control of 4-Chloro-2-methoxypyridine

(a); 5.76 g (40.1 mmol) of 4-chloro-2-methoxypyridine was dissolved in 20 ml of dimethylformamide, and a dimethylformamide (20 ml) solution of 8.01 g of N-bromosuccinimide (98%, 44.1 mmol) was dropwise added over a period of 30 minutes. After stirring at room temperature for 2 days, an unreacted material was confirmed, and thus 2.85 g of N-bromosuccinimide (98%, 16 mmol) was further added, followed by stirring at room temperature further for 3 days. The reaction mixture was poured into 250 ml of water, followed by extraction with ethyl ether (100 ml each) three times. The organic layer was washed with water (100 ml), a sodium thiosulfate aqueous solution (100 ml) and then a saturated sodium chloride solution (100 ml), dried over magnesium sulfate and subjected to filtration, and the solvent was distilled off under reduced pressure. The obtained crude product was purified by silica gel chromatography to obtain 7.10 g (yield: 80%) of 5-bromo-4-chloro-2-methoxypyridine. 1H-NMR(CDCl3, 400MHz): delta (ppm) =3.91 (s, 3H), 6. 89 (s,1H), 8.28(s,1H)

The synthetic route of 72141-44-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1679003; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1072438-56-2, 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.1072438-56-2, name is Methyl 6-(aminomethyl)nicotinate hydrochloride, molecular formula is C8H11ClN2O2, molecular weight is 202.6381, as common compound, the synthetic route is as follows.

Preparation 26Methyl 6-[(isobutyrylamino)methvHnicotinateTo an ice-cold suspension of methyl 6-(aminomethyl)nicotinate hydrochloride (1 .00 g, 4.1 8 mmol) and N-ethyl-N-isopropylpropan-2-amine (1 .89 g, 2.55 mL, 14.6 mmol) in DCM (10 mL) was added dropwise a solution of isobutyryl chloride (535 mg, 526 mu, 5.02 mmol) in DCM (3 mL). The reaction mixture was allowed to warm to room temperature, washed with water (5 mL), 1 0% aqueous citric acid solution (5 mL), saturated aqueous sodium bicarbonate solution (5 m L), brine (5 mL), dried over magnesium sulfate, filtered and evaporated to yield the title compound as a pale orange solid (0.988 g, 100%):1H NMR (400 MHz, CDCI3): delta 1 .22 (d, 6H), 2.45 – 2.55 (m, 1 H), 3.95 (s, 3H), 4.62 (d, 2H), 6.67 – 6.68 (br, 1 H), 7.32 – 7.36 (m, 1 H), 8.26 – 8.30 (m, 1 H), 9.15 (s, 1 H).LCMS Rt = 1 .72 minutes MS m/z 237 [MH]+

The chemical industry reduces the impact on the environment during synthesis 1072438-56-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PFIZER LIMITED; BROWN, Alan Daniel; RAWSON, David James; STORER, Robert Ian; SWAIN, Nigel Alan; WO2012/7869; (2012); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1042986-00-4, 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. 1042986-00-4, name is 2-Fluoro-5-methylnicotinic acid. A new synthetic method of this compound is introduced below.

To a cooled to 0 C. mixture of 4-amino-benzoic acid methyl ester (0.930 g, 61.7 mmol) and 2-fluoro-5-methylnicotinic acid (10.0 g, 64.5 mmol) was added a solution of HOBt (10.0 g, 74.0 mmol) in dry DMF (100 mL). EDC (11.0 g, 70.9 mmol) was added and the reaction mass was stirred overnight at room temperature. The resulting mixture was poured into cold water (600 mL). The precipitated solid was collected by filtration, washed with water, and dried in vacuum to obtain methyl 4-(2-fluoro-5-methylnicotinamido)benzoate (14.2 g, 80%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1042986-00-4, 2-Fluoro-5-methylnicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; Enanta Pharmaceuticals, Inc.; Kim, In Jong; Panarese, Joseph; Blaisdell, Thomas P.; Yu, Jianming; Shook, Brian C.; Or, Yat Sun; US2019/2478; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 132521-70-1, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 132521-70-1 as follows.

A suspension of 6-(4-methyl-piperazin-1-yl)-nicotinic acid (200 mg) in DMF (2 ml) was treated under an argon atmosphere with diisopropylamine (0.50 ml), benzylamine (0.12 ml) and BOP (600 mg). The reaction mixture was stirred at r.t. overnight, then diluted with water and extracted with EtOAc. The combined organic layers were washed with water and brine, dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (silica gel; gradient: CH2Cl2?CH2Cl2/MeOH 9:1) to give N-benzyl-6-(4-methyl-piperazin-1-yl)-nicotinamide (120 mg) as off-white solid. MS (ISP): 311.3 ([M+H]+)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,132521-70-1, its application will become more common.

Reference:
Patent; Galley, Guido; Zbinden, Katrin Groebke; Norcross, Roger; Stalder, Henri; US2009/36452; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 936011-17-5 ,Some common heterocyclic compound, 936011-17-5, molecular formula is C7H6BrNO2, 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.

Example 60b (20.5 g, 0.095 mol)was dissolved in THF (400 mL) the resulting solution was stirred at 0C under N2 then treated with LiAlH4 (3.9 g 0.1 mol), maintained the temp below 10C, After addition ,the colorless solution turned to purplish red and stirred at r.t. for 2hrs.TLC showed Compound 232 was consumed, water (4 mL) 15% NaOH (4 mL) and water (12 mL) was added successively the mixture was stirred at r.t for lhr, Na2S04 (50 g) was added, the suspension was filtered off and washed with EA (200 mL), the filtrate was concentrated to give the desired product (Example 60c, 9.4 g, yield 93%) as a brown oil. LCMS [M+H]+=218, 220.

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. 936011-17-5, 5-Bromo-2-methoxyisonicotinaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; (212 pag.)WO2017/218960; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 127406-55-7, 4-Pyridin-3-yl-benzaldehyde, 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, 127406-55-7, blongs to pyridine-derivatives compound. Recommanded Product: 127406-55-7

Methyl iodide (0. 8 ml, 12. 9 mmol) was added to a solution of 4- (3-PYRIDYL) benzaldehyde (0. 78 g, 4. 3 mmol) in dichloromethane and stirred 2 days. Additional methyl iodide (0. 8 ml, 12. 9 mmol) was added and stirred for 3 hr. After removal of the solvent, methanol was added to the residue and ice-cooled. Sodium tetrahydroborate (6. 4 g, 17. 0 mmol) was added to the solution and stirred for 1. 5 hr with warming to room temperature. Organic solvents were removed under reduced pressure after addition of water and extracted with ethyl acetate, washed with water and brine and dried over sodium sulfate. After removal of the solvent under reduced pressure, residue was purified by silica gel chromatography (eluent ethyl acetate to methanol) to give 3-(4-HYDROXYMETHYLPHENYL)-1-METHYL-1, 2, 5, 6- TETRAHYDROPYRIDINE (0. 63 g, 72%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,127406-55-7, its application will become more common.

Reference:
Patent; MITSUBISHI PHARMA CORPORATION; SANOFI-SYNTHELABO; WO2004/85408; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 89640-55-1, 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. 89640-55-1, name is 3-Iodo-4-methoxypyridine, molecular formula is C6H6INO, 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 the reaction mixture containing Intermediate IB (31.8 mg, 0.1 mmol) was added 3-iodo-4-methoxypyridine (125.5 mg, 0.534 mmol), sodium carbonate (68.1 mg, 0.643 mmol) and EtOH:DME:H20 (1.2:2.5: 1.0 ratio) (1.5 mL). The reaction mixture was purged with argon, then treated with tetrakis(triphenylphosphine)palladium (0) (23 mg, 0.020 mmol). The reaction mixture was purged with argon again, securely capped, and placed in a 105C oil bath for 2 h 45 min. The reaction mixture was cooled to room temperature, then diluted with DMF (4 mL). The resulting solution was filtered through a 0.45 uM frit attached to a single-use Waters C-18 sep-pak light cartridge (part No.WAT023501), and then purified by preparative HPLC (Condition A) using aPhenomenex Luna Axia 30 x 100 mm S10 column from 20% Solvent B to 85% Solvent B over 12 min, ret. T = 4.84 min to afford the title compound (12 mg, 31%) as a white solid. ¾ NMR (500 MHz, DMSO-d6) delta ppm 3.91-3.97 (m, 3 H), 4.04 (d, J=7.93 Hz, 2 H), 7.35 (d, J=3.36 Hz, 1 H), 7.49-7.58 (m, 1 H), 7.79-7.86 (m, 2 H), 8.40-8.47 (m, 1 H), 8.59-8.68 (m, 3 H), 8.78-8.85 (m, 2 H). LC/MS (Condition B): ret. T = 2.0min, (M+H)+ 382.04. Analytical HPLC: (Condition A): >97%, ret. T = 16.13 min, (Condition B):>97%, ret. T = 18.28 min, (Condition C): >98%, ret. T = 5.96 min, (Condition D): >98%, ret. T = 6.61 min.

According to the analysis of related databases, 89640-55-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; VELAPARTHI, Upender; FRENNESSON, David B.; SAULNIER, Mark G.; AUSTIN, Joel F.; HUANG, Audris; BALOG, James Aaron; VYAS, Dolatrai M.; WO2012/9510; (2012); 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. 477871-32-2, name is 6-Amino-5-bromonicotinonitrile. A new synthetic method of this compound is introduced below., COA of Formula: C6H4BrN3

5-(2-(3-((tert-butyldimethylsilyl)oxy)propyl)-2H-tetrazol-5-yl)-3-iodopyridin-2-amine The mixture of 6-amino-5-bromonicotinonitrile (3.315 g, 15.9 mmol, 1 eq), sodium iodide (4.77 g, 2 eq), copper(I) iodide (303 mg, 0.1 eq), and trans-N,N’-dimethylcyclohexane-1,2-diamine (0.52 mL, 0.2 eq) in anhydrous dioxane (40 mL under nitrogen atmosphere was stirred at 120 C. for 20 hours. The mixture was cooled to room temperature then partitioned between ethyl acetate and aqueous ammonium chloride. The organic layer was isolated, further washed with saturated aqueous sodium bicarbonate, brine, and dried with anhydrous sodium sulfate. The upper solution was decanted, concentrated, and the crude solid residue was subject to a column chromatography started first with EtOAc-Hex (1:5 to 1:1) followed by MeOH-CHCl3 (1:100 to 1:20). Product containing fractions were all collected and concentrated. The solid residue was triturated with EtOAc-Hex (1:4) yielding 3-iodo-5-isocyanopyridin-2-amine as an off-white solid in the amount of 2.75 g upon filtration. 1H NMR (600 MHz, DMSO-d6) delta ppm 8.35 (d, J=1.76 Hz, 1H) 8.30 (d, J=1.76 Hz, 1H) 7.14 (br. s., 2H).

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, 477871-32-2, 6-Amino-5-bromonicotinonitrile.

Reference:
Patent; Allergan, Inc.; Boral, Sougato; Malone, Thomas C.; Wang, Shimiao; Rao, Sandhya; Yang, Rong; (28 pag.)US2016/102081; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 109306-86-7, 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. 109306-86-7, name is 2-(2-Bromophenyl)pyridine, molecular formula is C11H8BrN, 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.

General procedure: Process (i) A dry 50-mL two-necked round bottom flask equipped with a glass stopper and a three-way stopcock was charged with 2-(2-chlorophenyl)pyridine (1.20 g, 6.32mmol) and CH2Cl2 (10 mL). The resulting colorless solution was cooled to 0 C, and mCPBA (1.64 g, 9.50mmol) was added slowly. The temperature was gradually raised to rt, and the colorless solution was stirred for 6 h. Cooling again to 0 C, 1M aq NaOH (10 mL) was slowly added. The organic layer was washed with 1M aq NaOH (10 mL) and brine (10 mL), and then dried over Na2SO4 (10 g). Filtration followed by evaporation gave nearly pure 2-(2-chlorophenyl)-pyridine-N-oxide (1.28 g) as a yellow oil. This was used for the next reaction without further purification.

According to the analysis of related databases, 109306-86-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Tanaka, Shinji; Suzuki, Yusuke; Kimura, Takahiro; Kitamura, Masato; Bulletin of the Chemical Society of Japan; vol. 92; 10; (2019); p. 1707 – 1720;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem