Category: 884494-51-3

Synthetic Route of 884494-51-3, 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. 884494-51-3, name is 2-Fluoro-4-iodonicotinic acid, molecular formula is C6H3FINO2, 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 2-(((3R.6R)-l-(ter?-butoxycarbonyl)-6-methylpiperidin-3-yl)oxy)-4- iodonicotinate A solution of 2-fluoro-4-iodonicotinic acid (4.43 g, 16.61 mmol) in DMSO (75 ml) was treated with sodium hydride (0.471 g, 19.62 mmol) in portions. After stirring a few minutes, (2R,5R)-tert-butyl 5-hydroxy-2-methylpiperidine-l-carboxylate (8, 3.25 g, 15.10 mmol) was added. Additional sodium hydride (0.362 g, 15.10 mmol) was added in portions and, after stirring for a few minutes, the reaction was heated at 40 C for 2 days. The reaction was cooled and quenched with saturated, aqu. NH4C1, then rapidly diluted with H2O and EtOAc. Cone. HCl was added until the the solution was acidic, then rapidly extracted 3x with EtOAc. The organics were washed 2x with H20, lx with brine, dried over MgS04, filtered, concentrated, and dried to provide the crude carboxylic acid. The crude foam was dissolved in DMF (76 mL) and cooled at 0 C and treated with sodium hydride (0.55 g, 23 mmol) in portions. After stirring ~10 mins, iodomethane (1.34 mL, 21.4 mmol) was added and the reaction was warmed to RT overnight. The reaction was cooled at 0 C and quenched by additon of saturated, aqu. NH4C1 and stirred well. Saturated, aqu. aHC03 was added and the reaction was extracted 2x with EtOAc. The organic fractions were washed with brine, dried over MgS04, filtered, and concentrated to provide the title compound as a crude oil. LRMS m/z (M+H) 477.3 found, 477.1 required.

According to the analysis of related databases, 884494-51-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; SKUDLAREK, Jason, W.; WO2014/62533; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 884494-51-3, 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. 884494-51-3, name is 2-Fluoro-4-iodonicotinic acid, molecular formula is C6H3FINO2, 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 2-(((3R.6R)-l-(ter?-butoxycarbonyl)-6-methylpiperidin-3-yl)oxy)-4- iodonicotinate A solution of 2-fluoro-4-iodonicotinic acid (4.43 g, 16.61 mmol) in DMSO (75 ml) was treated with sodium hydride (0.471 g, 19.62 mmol) in portions. After stirring a few minutes, (2R,5R)-tert-butyl 5-hydroxy-2-methylpiperidine-l-carboxylate (8, 3.25 g, 15.10 mmol) was added. Additional sodium hydride (0.362 g, 15.10 mmol) was added in portions and, after stirring for a few minutes, the reaction was heated at 40 C for 2 days. The reaction was cooled and quenched with saturated, aqu. NH4C1, then rapidly diluted with H2O and EtOAc. Cone. HCl was added until the the solution was acidic, then rapidly extracted 3x with EtOAc. The organics were washed 2x with H20, lx with brine, dried over MgS04, filtered, concentrated, and dried to provide the crude carboxylic acid. The crude foam was dissolved in DMF (76 mL) and cooled at 0 C and treated with sodium hydride (0.55 g, 23 mmol) in portions. After stirring ~10 mins, iodomethane (1.34 mL, 21.4 mmol) was added and the reaction was warmed to RT overnight. The reaction was cooled at 0 C and quenched by additon of saturated, aqu. NH4C1 and stirred well. Saturated, aqu. aHC03 was added and the reaction was extracted 2x with EtOAc. The organic fractions were washed with brine, dried over MgS04, filtered, and concentrated to provide the title compound as a crude oil. LRMS m/z (M+H) 477.3 found, 477.1 required.

According to the analysis of related databases, 884494-51-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; SKUDLAREK, Jason, W.; WO2014/62533; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 884494-51-3, 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 884494-51-3 as follows.

To a solution of 2-fluoro-4-iodonicotinic acid (5.13 g) in diethyl ether (25 mL)-methanol (25 mL) was added 10% trimethylsilyldiazomethane (hexane solution) (32.9 g), and the mixture was stirred under a nitrogen atmosphere at room temperature for 3 hr. The reaction solution was concentrated, and the residue was purified by silica gel chromatography (hexane-ethyl acetate) to give the title compound (5.3 g). 1H NMR (300 MHz, DMSO-d6) delta 3.94 (3H, s), 7.98 (1H, dd, J = 5.3, 1.1 Hz), 8.07 (1H, dd, J = 5.3, 0.8 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,884494-51-3, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; SUGIMOTO, Takahiro; NAKAMURA, Minoru; SAKAMOTO, Hiroki; SUZUKI, Shinkichi; YAMADA, Masami; KAMATA, Makoto; KOJIMA, Takuto; FUJIMORI, Ikuo; SHIMOKAWA, Kenichiro; EP2921480; (2015); A1;,
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. 884494-51-3, name is 2-Fluoro-4-iodonicotinic acid, molecular formula is C6H3FINO2, 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. Application In Synthesis of 2-Fluoro-4-iodonicotinic acid

To a solution of 401-C (10.3 g, 38.6 mmol) in 40 mL of MeOH and Et2O (40 mL) cooled with ice-water, TMSCH2N2(29 mL, 57.9 mmol) was added dropwise. The mixture was stirred at 25 C for overnight. Then ice water was added toquench the reaction. The solvent was removed by evaporation and Sat. NaHCO3 was added and the mixture was stirredfor 30 minutes. The mixture was extracted with EtOAc (100 mL3). The combined organic phase was washed with brine,dried over Na2SO4, filtered and concentrated to dry to give product 401-D (methyl 2-fluoro-4-iodonicotinate, 9.6 g, yield:88%).1H NMR (300 MHz, DMSO-d6): delta 8.06 (d, J = 5.4 Hz, 1H), 7.97 (d, J = 5.1 Hz, 1H), 3.93 (s, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 884494-51-3.

Reference:
Patent; Kangpu Biopharmaceuticals, Ltd.; LEE, Wen-Cherng; LIAO, Baisong; ZHANG, Lei; EP3590924; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 884494-51-3 ,Some common heterocyclic compound, 884494-51-3, molecular formula is C6H3FINO2, 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.

A suspension of 2-fluoro-4-iodonicotinic acid (896 mg, 3356 mumol) in 6M hydrochloric acid (13423 mul, 80540 mumol) was heated at 100 0C. After 5 min, the reaction became a solution, and then a precipitate appeared. The reaction mixture was stirred 60 min at 100 0C and then cooled to room temperature. Filtration afforded 2- hydroxy-4-iodonicotinic acid (710 mg, 2679 mumol, 80% yield). MS (ESI pos. ion) m/z: 248(M+H-H2O). Calc’d exact mass for C6H4INO3: 265.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,884494-51-3, its application will become more common.

Reference:
Patent; Amgen Inc.; WO2006/116713; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 884494-51-3, 2-Fluoro-4-iodonicotinic acid, 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, COA of Formula: C6H3FINO2, blongs to pyridine-derivatives compound. COA of Formula: C6H3FINO2

Step 1: Methyl 2-(((3R,6R)-1-(tert-butoxycarbonyl)-6-methylpiperidin-3-yl)oxy)-4-iodonicotinate (15) A solution of 2-fluoro-4-iodonicotinic acid (0.651 g, 2.44 mmol) in DMF (3 mL) was treated with sodium hydride (0.072 g, 3.0 mmol). After stirring ~5 minutes, tert-butyl (2R,5R)-5- hydroxy-2-methylpiperidine-1-carboxylate (Example 2, 8, 0.500 g, 2.32 mmol) and sodium hydride 10 (0.072 g, 3.0 mmol) were added, and the reaction was heated to 40 C for 1 hour. Iodomethane (0.73 mL, 0.012 mmol) was added, and the reaction was stirred at RT. After 1 hour, the mixture was diluted with ethyl acetate, washed with water and brine, dried over sodium sulfate, filtered, concentrated, and purified by silica gel chromatography eluting with 0-20% ethyl acetate in hexanes to provide the title compound as a colorless oil. LRMS m/z (M+H) 477.2 found, 477.2 required.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,884494-51-3, 2-Fluoro-4-iodonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; SKUDLAREK, Jason, W.; WO2015/88864; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 884494-51-3, 2-Fluoro-4-iodonicotinic acid, 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, COA of Formula: C6H3FINO2, blongs to pyridine-derivatives compound. COA of Formula: C6H3FINO2

Step 1: Methyl 2-(((3R,6R)-1-(tert-butoxycarbonyl)-6-methylpiperidin-3-yl)oxy)-4-iodonicotinate (15) A solution of 2-fluoro-4-iodonicotinic acid (0.651 g, 2.44 mmol) in DMF (3 mL) was treated with sodium hydride (0.072 g, 3.0 mmol). After stirring ~5 minutes, tert-butyl (2R,5R)-5- hydroxy-2-methylpiperidine-1-carboxylate (Example 2, 8, 0.500 g, 2.32 mmol) and sodium hydride 10 (0.072 g, 3.0 mmol) were added, and the reaction was heated to 40 C for 1 hour. Iodomethane (0.73 mL, 0.012 mmol) was added, and the reaction was stirred at RT. After 1 hour, the mixture was diluted with ethyl acetate, washed with water and brine, dried over sodium sulfate, filtered, concentrated, and purified by silica gel chromatography eluting with 0-20% ethyl acetate in hexanes to provide the title compound as a colorless oil. LRMS m/z (M+H) 477.2 found, 477.2 required.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,884494-51-3, 2-Fluoro-4-iodonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; SKUDLAREK, Jason, W.; WO2015/88864; (2015); 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. 884494-51-3, name is 2-Fluoro-4-iodonicotinic acid. A new synthetic method of this compound is introduced below., Quality Control of 2-Fluoro-4-iodonicotinic acid

To a solution of the product from step 2 (23.5 g, 88 mrnoi) in methanol (300 mL) was added dropwise TMSCHN2 (220 mL, 440 minol) at 05C under N2 . After addition was complete, the mixture was stirred at RT for 16 hrs, water was added and the mixture extracted with EtOAc (200 mL x 3). The combined organic layers were washed with brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. The crude product was purified bychromatography on silica (10% EtOAc in petroleum ether) to give the title compound as an oil. LRMS m/z M+H) 282.1 found, 282.1 required.

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, 884494-51-3, 2-Fluoro-4-iodonicotinic acid.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott D.; LIVERTON, Nigel; LUO, Yunfu; SKUDLAREK, Jason; (79 pag.)WO2016/95204; (2016); 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. 884494-51-3, name is 2-Fluoro-4-iodonicotinic acid. A new synthetic method of this compound is introduced below., Quality Control of 2-Fluoro-4-iodonicotinic acid

To a solution of the product from step 2 (23.5 g, 88 mrnoi) in methanol (300 mL) was added dropwise TMSCHN2 (220 mL, 440 minol) at 05C under N2 . After addition was complete, the mixture was stirred at RT for 16 hrs, water was added and the mixture extracted with EtOAc (200 mL x 3). The combined organic layers were washed with brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. The crude product was purified bychromatography on silica (10% EtOAc in petroleum ether) to give the title compound as an oil. LRMS m/z M+H) 282.1 found, 282.1 required.

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, 884494-51-3, 2-Fluoro-4-iodonicotinic acid.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott D.; LIVERTON, Nigel; LUO, Yunfu; SKUDLAREK, Jason; (79 pag.)WO2016/95204; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem