Category: pyridine-derivatives

Application of 1628-89-3, 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. 1628-89-3, name is 2-Methoxypyridine, molecular formula is C6H7NO, 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: A stirred cooled (0 C) solution of LiTMP prepared at 0 C in THF (6 mL) from 2,2,6,6-tetramethylpiperidine (1.7 mL, 10 mmol) and BuLi (1.6 M hexanes solution, 10 mmol) was treated with TMEDA (0.77 mL, 5.0 mmol) and CuCl (495 mg, 5.0 mmol). The mixture was stirred for 15 min at 0 C before introduction of the required substrate (5 mmol). After 2 h at rt, a solution of the required aroyl chloride (10 mmol) in THF (3 mL) was added. The mixture was stirred at rt or 60 C overnight before addition of a 1 M aqueous solution of NaOH (20 mL) and extraction with Et2O (220 mL). After washing the organic phase with an aqueous saturated solutionof NH4Cl (10 mL) and drying over anhydrous Na2SO4, the solvent was evaporated under reduced pressure, and the product was isolated after purification by flash chromatography on silica gel (the eluent is given in the product description).

According to the analysis of related databases, 1628-89-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Marquise, Nada; Harford, Philip J.; Chevallier, Floris; Roisnel, Thierry; Dorcet, Vincent; Gagez, Anne-Laure; Sable, Sophie; Picot, Laurent; Thiery, Valerie; Wheatley, Andrew E.H.; Gros, Philippe C.; Mongin, Florence; Tetrahedron; vol. 69; 47; (2013); p. 10123 – 10133;,
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 10592-27-5, name is 2,3-Dihydro-1H-pyrrolo[2,3-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. name: 2,3-Dihydro-1H-pyrrolo[2,3-b]pyridine

To a solution of sulfurisocyanatidic chloride (37 mg, 0.26 mmol) in DCM (2 mL) in an ice-water bath was added a solution of Intermediate GW-13.2 (100 mg, 0.26 mmol) and TEA (0.11 mL, 0.79 mmol) in DCM (2 mL) and the reaction mixture was stirred for 2 min. Then a solution of 2,3-dihydro-1H-pyrrolo[2,3-b]pyridine (48 mg, 0.39 mmol) in DCM (2 mL) was added, followed by TEA (0.15 mL, 1.1 mmol), the bath was removed and the stirring was continued at rt for 2 h. The reaction mixture was concentrated, the residue was redissolved in DMF and purified by preparative HPLC to afford the title compound (31.4 mg). LC-MS retention time = 3.06 min; m/z = 554.16 [M+Na]+. (Column: Phenomenex-Luna 2.0 X 50 mm, 3 mupiiota particles; Mobile Phase A: 10% MeOH- 90% H2O-0.1% TFA; Mobile Phase B: 90% MeOH-10% H2O-0.1% TFA; Temperature: 40 C; Gradient: 0-100% B over 4 min, then a 1-min hold at 100% B; Flow: 0.8 mL/min; Detection: UV at 220 nm).

With the rapid development of chemical substances, we look forward to future research findings about 10592-27-5.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BENDER, John A.; GENTLES, Robert G.; PENDRI, Annapurna; WANG, Alan Xiangdong; MEANWELL, Nicholas A.; BENO, Brett R.; FRIDELL, Robert A.; BELEMA, Makonen; NGUYEN, Van N.; YANG, Zhong; WANG, Gan; KUMARAVEL, Selvakumar; THANGATHIRUPATHY, Srinivasan; BORA, Rajesh Onkardas; HOLEHATTI, Shilpa Maheshwarappa; METTU, Mallikarjuna Rao; PANDA, Manoranjan; (319 pag.)WO2016/172424; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 109-04-6, 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.109-04-6, name is 2-Bromopyridine, molecular formula is C5H4BrN, molecular weight is 157.996, as common compound, the synthetic route is as follows.

2-Bromopyridine (2.00 mL), 3-aminophenylboronic acid (5.40 g) and palladium tetrakistriphenylphosphine (1.2512 g) were added to a mixture of 130 mL of dimethoxyethane and 32 mL of 2.0 M aqueous potassium carbonate under an atmosphere of dry N2. The reaction mixture was heated at 90 C overnight. The reaction mixture was then cooled to room temperature and diluted with water (300 mL). The resulting precipitate was collected, washed with water and air-dried. The dried material was purified using silica gel chromatography to give 2.75 g of 3-(pyridin-2-yl)benzenamine.

Statistics shows that 109-04-6 is playing an increasingly important role. we look forward to future research findings about 2-Bromopyridine.

Reference:
Patent; ARRAY BIOPHARMA, INC.; WO2007/130743; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 100137-47-1, name is 4-Aminopicolinamide, molecular formula is C6H7N3O, 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. COA of Formula: C6H7N3O

To a solution of 4-aminopyridine-2-carboxamide (2.90 g, 21.2 mmol) and DIEA (7.19 g, 55.7 mmol) in NMP (27 mL) at 0 C was added dropwise a solution of 2-fluoro-4-(trifluoromethoxy)benzoyl chloride (5.40 g, 22.3 mmol) in dichloromethane (27 mL). The reaction mixture was removed from the ice bath and stirred at room temperature for 16 hours. The reaction mixture was partitioned between water and ethyl acetate. The layers were separated and the aqueous layer was extracted with additional ethyl acetate. The combined organic layers were dried over Na2S04, filtered and concentrated in vacuo. The crude material was triturated with a mixture of hexanes/dichloromethane and the solid was collected by vacuum filtration to obtain 4-[[2-fluoro-4-(trifluoromethoxy)benzoyl]amino]pyridine-2-carboxamide (650 mg, 9%). ESI-MS m/z calc. 343.05, found 344.1 (M+l)+; retention time (Method B): 1.65 minutes(3 minute run). NMR (400 MHz, DMSO-d6) delta 1 1.09 (s, 1H), 8.56 (d, J = 5.6 Hz, 1H), 8.36 (d, J = 2.2 Hz, 1H), 8.1 1 (d, J = 2.7 Hz, 1H), 7.95 – 7.80 (m, 2H), 7.74 – 7.54 (m, 2H), 7.50 – 7.32 (m, 1H) ppm.

With the rapid development of chemical substances, we look forward to future research findings about 100137-47-1.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; AHMAD, Nadia; ANDERSON, Corey; ARUMUGAM, Vijayalaksmi; ASGIAN, Iuliana, Luci; CAMP, Joanne, Louise; FANNING, Lev Tyler, Dewey; HADIDA RUAH, Sara, Sabina; HURLEY, Dennis; SCHMIDT, Yvonne; SHAW, David; SHETH, Urvi, Jagdishbhai; THOMSON, Stephen, Andrew; (691 pag.)WO2019/14352; (2019); 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. 67443-38-3, name is 5-Bromo-2-chloro-3-nitropyridine, the common compound, a new synthetic route is introduced below. Recommanded Product: 5-Bromo-2-chloro-3-nitropyridine

To a suspension of sodium hydride (5.31 g, 133 mmol) in 1 ,4-dioxane (250 ml), ethyl glycolate (12.56 ml, 133 mmol) was added drop wise over a period of 30 minutes ensuring that the temperature was maintained below 30C. The resulting thick suspension was stirred at room temperature for 15 minutes. In a separate 11 round- bottomed flask was added 5-bromo-2-chloro-3-nitropyridine (21 g, 88 mmol) in 1 ,4- dioxane (150 ml) to give a brown solution. The suspension of sodium hydride and ethyl glycolate was added drop wise over a period of 30 minutes at 0C. The resulting reaction mixture was heated to 80C overnight. The reaction mixture was concentrated under reduced pressure and the crude residue was purified by Biotage silica chromatography (gradient 0% to 10% ethyl acetate in n- hexanes) to give the title compound (1 .8g, 44%). N R (500 MHz, CDCI3): 8.48 (1 H, s), 8.42 (1 H, s), 5.07 (2H, s), 4.28-4.24 (2H, q), 1.31-1.28 (3H, t).

The synthetic route of 67443-38-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMAC DISCOVERY LIMITED; ZHANG, Lixin; TREVITT, Graham, Peter; MIEL, Hughes; BURKAMP, Frank; HARRISON, Timothy; WILKINSON, Andrew, John; FABRITIUS, Charles-Henry; WO2011/77098; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 116026-94-9 ,Some common heterocyclic compound, 116026-94-9, molecular formula is C11H14N2O3, 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 mixture of the aldehyde (0.222 g, 1 mmol) and DMF (3 mL) was added MeI (0.178 g, 1.25 mmol) at 0 0C. NaH (0.052 g, 60% mineral oil, 1.35 mmol) was added in three portions over 15 min and the resulting yellowish suspension was stirred for an additional 60 min. The mixture was warmed to rt and quenched by the addition Of NaHCO3 (10 mL) and H2O (10 mL). The mixture was extracted with Et2O (3><1 OmL), and the combined organic layers were washed with H2O (10 mL), NaHCO3 (10 mL), brine (10 mL), and dried over Na2SO4. The product was further purified by flash chromatography (25% EtOAc in hexanes) to afford an oil (0.197 g, 84%), which was used in the next step

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. 116026-94-9, tert-Butyl (3-formylpyridin-2-yl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LAUTENS, Mark; YUEN, Josephine; FANG, Yuanqing; WO2008/22467; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 153034-90-3, 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. 153034-90-3, name is 2-Chloro-4-iodonicotinaldehyde, molecular formula is C6H3ClINO, 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.

According to GP1, 2-chloro-4-iodonicotinaldehyde (989 mg, 3.70 mmol), CsF (112 mg, 0.74 mmol), and t-BuMe2SiCN (784 mg, 5.60mmol) were dissolved in anhyd MeCN (3.7 mL). The reaction mixture was stirred at 25 C for 12 h. The resulting mixture was diluted with H2O (20 mL) and extracted with EtOAc (3 × 40 mL). The combined organic phases were dried (anhyd MgSO4), filtered, and the solvents were evaporated in vacuo. The crude product was purified by flash column chromatography on silica gel (i-hexane/EtOAc, 9:1 + Et3N 2%) yielding 2-(tert-butyldimethylsilyloxy)-2-(2-chloro-4-iodopyridin-3-yl)acetonitrile as a light yellow solid (1.5 g, 98%); mp 83.4-85.2 C.IR (Diamond-ATR, neat): 2955, 2859, 1636, 1548, 1472, 1337, 1302,1255, 1186, 1066, 939, 833, 781 cm-1.1H NMR (400 MHz, CDCl3): delta = 7.99 (d, J = 5.2 Hz, 1 H), 7.85 (d, J = 5.2Hz, 1 H), 6.24 (s, 1 H), 0.94 (s, 9 H), 0.31 (s, 3 H), 0.13 (s, 3 H).13C NMR (101 MHz, CDCl3): delta = 150.3, 149.9, 135.5, 132.5, 116.7,110.3, 65.2, 25.4, 18.0, -4.9, -5.1.MS (70 eV, EI): m/z (%) = 353 (28), 351 (79), 323 (52), 296 (4), 226(35), 224 (100), 209 (12), 150 (6).HRMS (EI): m/z [M – C4H9]+ calcd for C9H9ClIN2OSi: 350.9217; found:350.9210.

According to the analysis of related databases, 153034-90-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Castello-Mico, Alicia; Knochel, Paul; Synthesis; vol. 50; 1; (2018); p. 155 – 169;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 16135-36-7, Methyl 4-aminonicotinate, 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

A mixture of 4-chloro-5-isopropenyl-2 -phenyl-pyridine (1.2 g, 5.24 mmol), methyl 4- aminopyridine-3-carboxylate (795 mg, 5.225 mmol) and Cs2C03 (3.40 g, 10.435 mmol) in dioxane (30 mL) was purged with nitrogen for 30 min, followed by addition of Pd2(dba)3 (478 mg, 0.521 mmol) and xantphos (604 mg, 1.043 mmol) and again purged with nitrogen for 5 min. The reaction mixture was heated at 100 C overnight. The progress of reaction was monitored over LCMS. After completion of the reaction, the reaction mixture was diluted with water (100 mL) and extracted with EtOAc (2×150 mL). The combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford a crude product, which was purified by column chromatography on silica gel (100-200 mesh) using 20% EtOAc- hexane as eluent to obtain methyl 4-[(5-isopropenyl-2-phenyl-4- pyridyl)amino]pyridine-3-carboxylate (500 mg) as a yellow sticky semi-solid

At the same time, in my other blogs, there are other synthetic methods of this type of compound,16135-36-7, Methyl 4-aminonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; MEDIVATION TECHNOLOGIES, INC.; RAI, Roopa; CHAKRAVARTY, Sarvajit; PUJALA, Brahmam; SHINDE, Bharat Uttam; NAYAK, Anjan Kumar; CHAKLAN, Naveen; AGARWAL, Anil Kumar; RAMACHANDRAN, Sreekanth A.; PHAM, Son; WO2015/103355; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 183208-35-7 ,Some common heterocyclic compound, 183208-35-7, molecular formula is C7H5BrN2, 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 G-1 : Preparation of (2S)-1-(4-(3-(3-chloro-1H-pyrrolo[2,3-b]pyridin-5-yl)-1- (tetrahydrofuran-3-yl)-1H-pyrazol-4-yl)pyrimidin-2-ylamino)propan-2-olPreparation of methyl 1H-pyrrolo[2,3-b]pyridine-5-carboxylate (G-1 -1a)G-1-1 G-1 -1aA mixture of 5-bromo-1 H-pyrrolo[2,3-b]pyridine (90 g, 0.4 mol) and dppp (3 g, 0.072 mol) in DMSO (300 mL) and MeOH (300 mL) was added Pd(OAc)2 (16.5 g, 0.072 mol). The resulting mixture was degassed under N2 for 2 min and then heated to 1000C under 2 MPa of CO gas for two days. TLC (Petroleum ether: EtOAc = 4:1 ) showed the reaction was complete. The mixture was cooled and filtered then concentrated. The obtained residue was poured into ice-water. The formed solid was collected and dried in vacuum to give crude compound 5 (86.1 g, crude), which was directly used to the next reaction without further purification.

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. 183208-35-7, 5-Bromo-1H-pyrrolo[2,3-b]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER INC.; WO2009/16460; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 55304-75-1, 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 55304-75-1, name is 2,6-Dichloro-3-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A DMF/water solution (1:1, 2 mL per 1 mmol of 1) of K3PO4 (1.5 mmol), Pd(OAc)2(2 mol %), and arylboronic acid 2 (2.2 mmol) was stirred at room temperaturefor 8-12 h (tlc control). After completion of the reaction, the mixture wasextracted with CH2Cl2 and the combined organic layers were dried (Na2SO4), filtered and the filtrate was concentrated in vacuo. The residue was purified bycolumn chromatography (silica gel, EtOAc/heptane = 1:4). Starting with 1(216 mg, 1.0 mmol), K3PO4 (345 mg, 2.5 mmol), Pd(OAc)2 (2 mol %), arylboronic acid (334 mg, 2.20 mmol), and solution of DMF andwater (1:1) (2 mL), 4a-f was isolated as a yield.

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 55304-75-1, 2,6-Dichloro-3-(trifluoromethyl)pyridine.

Reference:
Article; Ahmed, Shahzad; Sharif, Muhammad; Shoaib, Khurram; Reimann, Sebastian; Iqbal, Jamshed; Patonay, Tamas; Spannenberg, Anke; Langer, Peter; Tetrahedron Letters; vol. 54; 13; (2013); p. 1669 – 1672;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem