Month: April 2022

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. 22280-60-0, name is 6-Chloro-2-methyl-3-nitropyridine. A new synthetic method of this compound is introduced below., Safety of 6-Chloro-2-methyl-3-nitropyridine

6-methoxy-3-nitro-2-picoline 0.46 gm (20 mMol) sodium were dissolved in 15 mL anhydrous methanol. To this solution were added 2.3 gm 6-chloro-3-nitro-2-picoline in portions. The resulting mixture was stirred for 18 hours at room temperature and then 1 hour at reflux. The reaction mixture was poured into 100 mL of ice water with vigorous stirring. The suspension was filtered and the solid dried at 30 C. under reduced pressure for 18 hours to provide 2.04 gm (91%) of the desired compound as a tan solid.

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, 22280-60-0, 6-Chloro-2-methyl-3-nitropyridine.

Reference:
Patent; Eli Lilly and Company; US5874427; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 113293-70-2, 2,6-Dichloroisonicotinaldehyde, 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, 113293-70-2, blongs to pyridine-derivatives compound. Product Details of 113293-70-2

Step 23a: tert-butyl 4-((2,6-dichloropyridin-4-yl)methyl)piperazine-1-carboxylate (Intermediate 23a) 2,6-dichloroisonicotinaldehyde (106 mg, 0.6 mmol), N-Boc-piperizane (112 mg, 0.6 mmol) and 320 mg of NaBH(OAc)3 powder was stirred in 5 mL of dichloromethane at room temperature for 1 hr. 3 mL of saturated NaHCO3 aqueous solution was added, the reaction mixture was stirred for additional 30 min. After regular aqueous workup with dichloromethane-water, the reaction mixture was subject to column chromatography on silica gel, eluting with heptane/ethyl acetate (v/v 3/1), giving 150 mg of desired product as colorless oil. MS: m/z 346.0 (ES+); 290.0 (M-Bu-t, ES+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,113293-70-2, its application will become more common.

Reference:
Patent; AVILA THERAPEUTICS, INC.; US2011/230476; (2011); 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. 167837-43-6, name is (E)-3-(6-Aminopyridin-3-yl)acrylic acid. A new synthetic method of this compound is introduced below., Quality Control of (E)-3-(6-Aminopyridin-3-yl)acrylic acid

EDC (231 mg, 1.2 mmol) was added to a solution of (E)-3-(6-AMINO-PYRIDIN-3- yl) acrylic acid (164 mg, 1.0 mmol), (2-ethoxy-3-methoxy-benzyl) methylamine (215 mg, 1.1 mmol), HOT HO (149 mg, 1.1 mmol) and DIPEA (525 1L, 3.0 mmol) in dry DMF (10 mL). After 18 hr of stirring, the mixture was diluted with water (60 mL) and extracted with EtOAc (2X20 mL). The organic layer was washed with brine (2×30 mL), dried and evaporated. Flash chromatography (silica 1-3% MEOH in CH2CL2) furnished pure free base which was dissolved in CH2CL2 (10 mL). After addition of HCl (1.5 mL, 1M in ether), the solvents were evaporated and the residue was washed with ether and dried to afford the title compound (172 mg, 46%). 1H NMR (300 MHz, DMSO-d6) 8 8.28 (m, 3H), 7.48 and 7.45 (rotamers, 2d, J= 15.4 Hz, 1H), 7.25 and 7.23 (rotamers, 2d, J= 15.4 Hz, 1H), 7.00 (m, 3H), 6.62 (m, 1H), 4.78 and 4.63 (rotamers, 2s, 2H), 3.98 (m, 2H), 3.79 (s, 3H), 3.08 and 2.84 (rotamers, 2s, 3H), 1.28 (m, 3H). MS (ESI) mle 342 (M+H) +.

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, 167837-43-6, (E)-3-(6-Aminopyridin-3-yl)acrylic acid.

Reference:
Patent; AFFINIUM PHARMACEUTICALS, INC.; WO2004/52890; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1192813-41-4, 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 1192813-41-4 as follows.

Step-2 -Preparation of 6-(difluoromethoxy)pyridin-3-amine To a solution of 2-(difluoromethoxy)-5-nitropyridine (0.900 g, 2.35 mmol) in ethanol (5.0 mL), was added iron powder (0.400 g, 7.14 mmol) and conc. HCl (0.2 mL). The reaction mass was refluxed for 1/2 h. Ethanol was removed under vacuum. To the reaction mass, water was added, basified with NaHCO3 and extracted with DCM. The organic layer was separated, dried over anhydrous sodium sulphate and concentrated to afford 0.400 g of the desired product. 1HNMR (DMSO-d6): delta 7.65 (s, 1H), 7.52-7.03 (t, J=72.0 Hz, 1H), 7.27 (s, 1H), 6.73 (d, J=8.4 Hz, 1H); MS [M-H]-: 159.14.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1192813-41-4, its application will become more common.

Reference:
Patent; Glenmark Pharmaceuticals S.A.; US2012/108583; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.178421-21-1, name is Ethyl 6-chloro-5-methylpicolinate, molecular formula is C9H10ClNO2, molecular weight is 199.63, as common compound, the synthetic route is as follows.name: Ethyl 6-chloro-5-methylpicolinate

l-[(2,2-difluorocyclopropyl)methyl]-3-methyl-5-(4,4,5,5-tetramethyl-1,3 ,2- dioxaborolan-2-yl)-1,3 -dihydro-2,1,3-benzothiadiazole 2,2-dioxide (12-1) (100 mg, 0.25 mmol, 1 eq), ethyl 6-chloro-5-methylpyridine-2-carboxylate (26-4) (75 mg, 0.38 mmol, 1.5 eq), tripotassium phosphate (106 mg, 0.50 mmol, 2.0 eq), S-Phos (10 mg, 0.025 mmol, 0.1 eq), and palladium(II) acetate (2.8 mg, 0.012 mmol, 0.05 eq) were combined in THF (1 mL) and water (0.2 mL). The resulting mixture was heated at 75 C for 14 hours. The reaction mixture was allowed to cool to room temperature. The mixture was then diluted with EtOAc (10 mL), washed with water (1 mL) and brine (1 mL), dried over MgS04, filtered and concentrated. The crude residue was purified by flash chromatography (12 g Si02, 0-80% EtOAc in hexanes) to afford ethyl 6- { 1 -[(2,2-difluorocyclopropyl)methyl]-3-methyl-2,2-dioxido- 1 ,3-dihydro-2, 1 ,3- benzothiadiazol-5-yl}-5-methylpyridine-2-carboxylate (26-5). HRMS m/z (M+H) 438.1291 found, 438.1294 required.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,178421-21-1, Ethyl 6-chloro-5-methylpicolinate, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LAYTON, Mark, E.; KELLY, Michael, J.; HARTINGH, Timothy, J.; WO2011/109277; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 4214-74-8 , The common heterocyclic compound, 4214-74-8, name is 3,5-Dichloropyridin-2-amine, molecular formula is C5H4Cl2N2, 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.

Step 1: 2-bromo-3,5-dichloropyridine [0239] To a solution of 3,5-dichloropyridin-2-amine (1.0 g, 6.2 mmol) in 40% aqueous HBr (8 mL) was added dropwise bromine (2.8 g, 17 mmol) at -20C. The orange suspension was stirred for 2hrs at -20C, and followed by addition of the aqueous NaN02 (1.1 g, 17 mmol) at -20C. The mixture thus obtained was stirred for an additional 2 hours at ambient temperature. The brown mixture was basified with 30% aqueous NaOH to pH ~12 at 0C. The pale yellow mixture was extracted with ether. The combined organic phases were washed with brine, dried over Na2S04 and concentrated to afford the title compound as yellow solid (730 mg, 52%). 1H NMR (400 MHz, CDC13) delta 8.27 (d, J J= 2.3 Hz, 1H).

The synthetic route of 4214-74-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RUGEN HOLDINGS (CAYMAN) LIMITED; SHAPIRO, Gideon; (119 pag.)WO2015/187845; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 850429-51-5, 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. 850429-51-5, name is Ethyl 6-amino-5-bromonicotinate, molecular formula is C8H9BrN2O2, 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) To a solution of ethyl 6-amino-5-bromonicotinate (2.31 g, 10 mmol) in tetrahydrofuran (20 mL) at RT was added LAH (10 mL, IM in tetrahydrofuran) dropwise. After stirring for Ih, the mixture was quenched with water (0.2 mL) and the resultant precipitate was filtered and washed with ethyl acetate. The filtrate was concentrated in vacuo to afford (6-amino-5-bromopyridin-3-yl)methanol (2.0 g, 99%) as a solid. LC/MS; (M+H)+ = 203, 205 (1 : 1 ratio). 1H NMR (CD3OD, 300 MHz) delta 7.79 (s, IH), 7.67 (s, IH), 4.35 (br S, 2H).

According to the analysis of related databases, 850429-51-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/60907; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 147740-04-3, Adding some certain compound to certain chemical reactions, such as: 147740-04-3, name is Ethyl 1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate,molecular formula is C10H12N2O2, 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 147740-04-3.

d) 2,3-Dihydro-1H-pyrrolo[3,4-c]pyridine dihydrochloride 10.4 g (51 mmol) of ethyl 2,3-dihydro-1H-pyrrolo-[3,4-c]pyridine-2-carboxylate are refluxed for 15 hours together with 100 ml of concentrated hydrochloric acid. The batch is evaporated, and the crystalline residue is stirred with acetone. The product is filtered off with suction and dried in the air. Yield: 9.8 g (100percent of theory)

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. 147740-04-3, Ethyl 1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bayer Aktiengesellschaft; US5312823; (1994); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 709652-82-4 , The common heterocyclic compound, 709652-82-4, name is 2-Amino-5-bromonicotinonitrile, molecular formula is C6H4BrN3, 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 126 Step 1: (6-amino-5-cyanopyridin-3-yl)boronic acid and 2-amino-5-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)nicotinonitrile To a stirred solution of 2-amino-5-bromonicotinonitrile (100 mg, 0.51 mmol) and 1,2- dimethoxyethane (4 mL) in a microwave vial equipped with a stirbar was added bis(pinacolato diborane) (175 mg, 0.66 mmol), potassium acetate (149 mg, 1.52 mmol) and 1,1′- bis(diphenylphosphino)ferrocene-palladium(II)dichloride (21 mg, 0.025 mmol). The mixture was purged with nitrogen gas for 5 min and the reaction mixture was stirred at 90 C for 3 h. The reaction mixture was filtered through a celite bed and washed with dichloromethane (10 mL). The filtrate was concentrated to dryness in vacuo affording a crude mixture of (6-amino-5-cyanopyridin-3-yl)boronic acid and 2-amino-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)nicotinonitrile used for the next step without any further purification. Step 2: 2-amino-5-(4-cyclopropyl-6,6-dimethyl-8,9-dihydro-6H-[l,4]oxazino[4,3-e]purin-2- yl)nicotinonitrile 2-chloro-4-cyclopropyl-6,6-dimethyl-8,9-dihydro-6H-[l,4]oxazino[4,3-e]purine (50 mg, 0.18 mmol) and a crude mixture of (6-amino-5-cyanopyridin-3-yl)boronic acid and 2-amino-5-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)nicotinonitrile (120 mg) was dissolved in acetonitrile (2.5 mL) and degassed water (0.5 mL) in a microwave vial equipped with a stirbar. To the solution was added bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (12.7 mg, 0.018 mmol), potassium acetate (25 mg, 0.25 mmol) and sodium carbonate (27 mg, 0.25 mmol) and the mixture was microwaved at 140 C for 40 min. The reaction mixture was filtered through a celite bed and washed with dichloromethane (10 mL). The filtrate was concentrated to dryness in vacuo. The resulting residue was purified by RP-HPLC affording 2-amino-5-(4-cyclopropyl-6,6-dimethyl-8,9-dihydro-6H- [l,4]oxazino[4,3-e]purin-2-yl)nicotinonitrile (4.1 mg, 6%, two steps): LCMS RT = 5.07 min, m/z = 362.2 [M + H]+.

The synthetic route of 709652-82-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; HUESTIS, Malcolm; KELLAR, Terry; PATEL, Snahel; SHORE, Daniel; SIU, Michael; (260 pag.)WO2016/142310; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1019021-85-2, 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.1019021-85-2, name is 6-Fluoroimidazo[1,2-a]pyridine-3-carboxylic acid, molecular formula is C8H5FN2O2, molecular weight is 180.1359, as common compound, the synthetic route is as follows.

Oxalyl chloride (10 mL, 1 10 mmol) was added dropwise to a stirred suspension of 6- fluoroimidazo[1 ,2-a]pyridine-3-carboxylic acid (24b) (2 g, 1 1 mmol) and catalytic amounts of DMF in dichloromethane (20 mL). After 5 hours, the solvent was evaporated and the solid was suspended in dry DCE (20 mL) and added to a stirred solution of 3- amino-4-methylbenzonitrile (1 .45 g, 1 1 mmol) and DIEA (6 mmol) in DCE (1 0 mL) at 0 C. After the addition, the reaction was heated at 60 C for 5 hours. The mixture was subjected to standard aqueous work and silica purification to give N-(5-cyano-2- methylphenyl)-6-fluoroimidazo[1 ,2-a]pyridine-3-carboxamide (39) as a solid. 1 H NMR (400MHz, c/6-DMSO) delta 10.14 (s, 1 H), 9.45 (dd, J = 5.2, 2.0 Hz, 1 H), 8.62 (s, 1 H), 7.90 – 7.87 (m, 2 H), 7.68-7.63 (m, 1 H), 7.53 (d, J = 8.0 Hz, 1 H), 2.37 (s, 3H). MS m/z 295.1 (M+1 ) +.

Statistics shows that 1019021-85-2 is playing an increasingly important role. we look forward to future research findings about 6-Fluoroimidazo[1,2-a]pyridine-3-carboxylic acid.

Reference:
Patent; IRM LLC; LOREN, Jon; LI, Xiaolin; LIU, Xiaodong; MOLTENI, Valentina; NABAKKA, Juliet; NGUYEN, Bao; PETRASSI, Hank Michael James; YEH, Vince; RUCKER, Paul Vincent; WO2013/33203; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem