Tag: M.W:200-300

Application of 867279-13-8, 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 867279-13-8, name is 4-Bromo-2-chloro-5-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

4-(4,4,5,5-Tetramethyl- [1,3,2]dioxaborolan-2-yl)-1-(2,4,6-trimethylbenzensulfonyl)-1H pyrrole-2- carboxylic acid methyl ester (125 mg, 0.29 mmol, 0.6 equiv. ) and 4-bromo-2- chloro-5-methylpyridine (96 mg, 0.47 mmol, 1.0 equiv. ) were dissolved in benzene (4 mL). After adding methanol (0.94 mL) and aqueous Na2C03, Pd (PPh3)4 (108 mg, 0.094 mol, 0.2 equiv. ) was then added and the resulting mixture was heated at reflux for 16 hours. The reaction mixture was dissolved in ethyl acetate and washed with water. After drying the organic layer over Na2S04, the solvent was removed under reduced pressure. The crude material was purified by reversed phase HPLC (acetonitrile/ water/TFA), yielding the title compound as a colorless solid (54 mg, 0.125 mmol, HPLC Rt 9.087 min, ES+ 433.0, ES- 431.0).

According to the analysis of related databases, 867279-13-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS, INCORPORATED; WO2005/100342; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 22282-70-8, name is 2-Fluoro-4-iodopyridine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 2-Fluoro-4-iodopyridine

A solution of 401-A (21.6 g, 96.9 mmol) in 100 mL of dry THF was cooled to -70 C. The above LDA solutionwas added dropwise to the solution while the temperature was kept below -70 C. Then the solution was stirred at -70C for 1 hour. Ethyl formate (10 mL, 121 mmol) was added dropwise to the solution and slowly warmed to -50 C during1 hour. The reaction mixture was quenched with sat. NH4Cl and stirred at 25 C for 30 minute. THF was removed byevaporation and the reaction solution was extracted with EtOAc (300 mL2). The combined organic phase was washedwith water and brine, dried over Na2SO4. Na2SO4 was filtered and the organic phase was concentrated to dry and theresidue was purified by column chromatography on silica gel (PE/EtOAc: 50:1 to 10:1) to give the product 401-B (2-fluoro-4-iodonicotinaldehyde, 13.0 g, yield: 53%).1H NMR (300 MHz, DMSO-d6): delta 10.15 (s, 1H), 7.97 (d, J = 5.1 Hz, 1H), 7.87 (d, J = 5.1 Hz, 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, 22282-70-8, 2-Fluoro-4-iodopyridine.

Reference:
Patent; Kangpu Biopharmaceuticals, Ltd.; LEE, Wen-Cherng; LIAO, Baisong; ZHANG, Lei; EP3590924; (2020); 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

Synthetic Route of 1227384-81-7, 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. 1227384-81-7, name is 2-Bromo-5-(ethylsulfonyl)pyridine, molecular formula is C7H8BrNO2S, 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.

Under nitrogen atmosphere,750 mg of 2-bromo-5- (ethanesulfonyl) pyridine,811 mg of 3- (trifluoromethanesulfonyl) aniline,Potassium t-butoxide 504 mg,And a mixture of 10 mL of 1,4-dioxaneTris (dibenzylideneacetone) dipalladium (0)60 mg and54 mg of 1,3-bis (2,6-diisopropylphenyl) imidazolium chloride are sequentially added,Stir at 100 C.After completion of the reaction, the resulting mixture is brought to room temperature,Add water and extract with ethyl acetate.The resulting organic layer is washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure.The resulting residue is subjected to silica gel column chromatography.2-{[3- (Trifluoromethanesulfonyl) phenyl] amino} -5- (ethanesulfonyl) pyridine is obtained.

According to the analysis of related databases, 1227384-81-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sumitomo Chemical Chemicals company; Sasayama, Daisuke; Inui, Tomohiko; (102 pag.)JP2019/48845; (2019); 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 1227605-52-8, name is 2-Bromo-5-chloronicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

To a solution of 2,3-dibromo-5-chloropyridine (60 g, 221 mmol) in THF (500 mL) was added a solution of isopropylmagnesium chloride lithium chloride solution in THF (1.3M, 185 mL) at -40 C over about 30 min. The solution was stirred for 30 min at -40 C and DMF (50 mL) was added. The resulting solution was warmed up to room temperature and stirred for 30 min. The reaction was quenched with 1 N HCl (400 mL) and MTBE (200 mL) was added. Organic layer was separated and washed twice with 5% aqueous NaHC03 (200 mL). The solvent was removed under vacuum at 50 C. The resulting solids (aldehyde intermediate) were dissolved in methanol (400 mL). The solution was cooled to 5 C under an ice bath. NaBtit (3.6 g) was added slowly over 30 min while maintaining the reaction temperature below room temperature. The reaction mixture was stirred for another 30 min followed by addition of water (125 mL). The resulting mixture was concentrated under vacuum to approximately 150 ml. Solids precipitated during the concentration. The suspension was stirred vigorously at room temperature for 1 h and solids were collected by filtration. The wet cake was dried in a vacuum oven over night at 60 C to give 1 (45.6 g, 93%) as a solid. 1H NMR (CDC13) 400 MHz): <5 8.26 (d, J= 2.5 Hz, 1H), 7.88 (d, J=2.5 Hz, IK), 4.73 (d, J= 5.8 Hz, 2H), 2.33 (t, J= 1 1.4 Hz, 1H); 13C NMR (CDC13, 100 MHz): delta 147.12, 138.48, 138.39, 136.14, 132.06, 62.76. With the rapid development of chemical substances, we look forward to future research findings about 1227605-52-8. Reference:
Patent; MERCK SHARP & DOHME CORP.; XIANG, Bangping; YASUDA, Nobuyoshi; WO2013/138413; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 951625-93-7, Methyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate, 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, HPLC of Formula: C9H7ClN2O2, blongs to pyridine-derivatives compound. HPLC of Formula: C9H7ClN2O2

To a solution of 4-chloro-1H-pyrrolo[2,3-bjpyridine-5-carboxylic acid methyl ester (0.65 g, 3.1 mmol) in DMF (6.0 mL) was added NaH (60%, 149 mg, 3.72 mmol) at 0C. The mixture was stirred at rt for lh. Mel (572 mg, 4.03 mmol) was added to the reaction and stirred at rt overnight. The reaction was quenched with sat. NH4C1 solution (10 mL) and separated between water (20 mL) and EA (30 mL). The organic layer was washed with water (10 mL) and brine (10 mL), dried over anhydrous Na2SO4. The solvent was removed to give 4-chloro-1-methyl-1H-pyrrolo[2,3-bjpyridine-5-carboxylic acid methyl ester (0.75 g, yield:quantitative) as yellow crystal.?HNMR (400 MI-Tz, CDC13): = 8.86 (s, 1H), 7.26 (overlap, 1H), 6.68 (d, J= 3.6 Hz, 1H), 3.97 (s, 3H), 3.91 (s, 3H).

The synthetic route of 951625-93-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; PINKERTON, Anthony, B.; HASSIG, Christian, A.; JACKSON, Michael, R.; ARDECKY, Robert, John; PASS, Ian; (436 pag.)WO2016/123392; (2016); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 878197-68-3, 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 878197-68-3, name is 5-Bromoimidazo[1,2-a]pyridine-2-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

The reactor is charged with N-methylpiperazine (3.1 Kg, 31 mol ) and tetrahydrofuran (10 Liters) and stirred under nitrogen while cooling to negative 20 0C. n-Butyl lithium (10.4 L, 26.0 mol) is added to the reaction at a rate to maintain the negative 200C temp and the contents are stirred for 15 to 30 minutes. A slurry of 5- bromoimidazo[1 ,2-a]pyridine-2-carbaldehyde (2.79 Kg, 12.4 mol) in tetrahydrofuran (10 Liters) is added at a rate to maintain the reaction at ?0C. The slurry is washed in with additional tetrahydrofuran (6 Liters). The reaction is stirred for 30 minutes and warmed to approximately negative 100C. The reaction is quenched by addition of 6N HCI solution to achieve pH 4.0 while maintaining at ? 150C. The reaction is diluted with heptane (14 Liters) and the layers allowed to separate. The lower aqueous layer is drained and the upper organic layer is washed with 1N HCI (2 x 1.5 Liters). The combined aqueous layers are stirred at 20 degrees and adjusted to pH 9 with 4N NaOH solution. The Aqueous layer is extracted with 10% iPrOH/CH2CI2 (3 x 28 Liters) and the combined organic layers are washed with saturated NaHCO3 solution (14 Liters) and evaporated at <250C to approximately 3 volumes, lsopropanol (28 Liters) is added and reaction again concentrated under reduced pressure to approximately 8.5 Liters, lsopropanol (17 Liters) is added and the reaction is treated with a solution of oxalic acid (1.0 Kg, 11.1 mol) in isopropanol (7 Liters) at a rate to maintain good stirring and temperature between approximately 25-4O0C. The reaction is stirred for 30 minutes and the solids are collected and washed with isopropanol (8.5 Liters) Solids are dried at 50 0C to yield 5-(4-methyl-1- piperazinyl)imidazo[1,2-a]pyridine-2-carbaldehyde, (2.25 Kg, 54% yield) 1H NMR (400 MHz, DMSO-D6) delta ppm 10.01 (s, 1 H) 8.47 (s, 1 H) 7.41 (m, 2 H) 6.65 (m, 1 H) 3.34 (s, 8 H) 2.78 (s, 3 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 878197-68-3, 5-Bromoimidazo[1,2-a]pyridine-2-carbaldehyde.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/87549; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1235036-15-3, 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.1235036-15-3, name is tert-Butyl 3-bromo-6-chloropicolinate, molecular formula is C10H11BrClNO2, molecular weight is 292.56, as common compound, the synthetic route is as follows.

Example 1E tert-butyl 6-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-3-bromopicolinate EXAMPLE 1D (0.736 g), EXAMPLE 1C (1.62 g), and Cs2CO3 (4.1 g) were stirred in 12 mL of anhydrous N,N-dimethylacetamide at 120 C. for 12 hours. The cooled reaction mixture was then diluted with ethyl acetate and 10% citric acid. The organic phase was washed three times with citric acid, once with water and brine, and dried over Na2SO4. Filtration and concentration afforded crude material, which was chromatographed on silica gel using 0-40% ethyl acetate in hexanes to provide the title compound.

The chemical industry reduces the impact on the environment during synthesis 1235036-15-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; AbbVie Inc.; WANG, LE; Doherty, George; Wang, Xilu; Tao, Zhi-Fu; Bruncko, Milan; Kunzer, Aaron R.; Wendt, Michael D.; Song, Xiaohong; Frey, Robin; Hansen, Todd M.; Sullivan, Gerard M.; Judd, Andrew; Souers, Andrew; US2013/96120; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 190271-88-6, 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.190271-88-6, name is Methyl 2-chloro-5-nitronicotinate, molecular formula is C7H5ClN2O4, molecular weight is 216.58, as common compound, the synthetic route is as follows.

The fourth step of Scheme 4: To a 5 mL DMF solution of 2-chloro-5-nitronicotinic acid methyl ester (269 mg, 1.25 mmole) was added methyl thioglycolate (111 muL, 1.25 mmole) followed by potassium carbonate (428 mg, 3.1 mmole) and the mixture was stirred at room temperature overnight. The reaction mixture was then poured into 50 mL water and extracted with CH2Cl2. The aqueous phase was acidified with 2N HCl and extracted with CH2Cl2. Combined organic phases were washed with water and dried over MgSO4. The solids were removed by filtration and the solvent was evaporated under reduced pressure to give 240 mg (76%) 3-hydroxy-5-nitro-thieno[2,3-b]pyridine-2-carboxylic acid methyl ester as a tan colored solid. 1H NMR (400 MHz, CHLOROFORM-D) delta ppm 4.02 (s, 3H) 9.01 (d, J=2.53 Hz, 1H) 9.52 (d, J=2.53 Hz, 1H) 10.19 (s, 1H).

Statistics shows that 190271-88-6 is playing an increasingly important role. we look forward to future research findings about Methyl 2-chloro-5-nitronicotinate.

Reference:
Patent; Lee, Jinbo; Kirincich, Steve J.; Smith, Michael J.; Wilson, Douglas P.; Follows, Bruce C.; Wan, Zhao-Kui; Joseph-McCarthy, Diane M.; Erbe, David V.; Zhang, Yan-Ling; Xu, Weixin; Tam, Steve Y.; US2005/203081; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 7169-95-1 ,Some common heterocyclic compound, 7169-95-1, molecular formula is C7H6BrN3, 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 5(S)-6-(2-hydroxy-2-methylpropyl)-6-isopropyl-3-((S)-l-(4-(2-methyl-[l,2,4]triazolo[l,5-a]pyridin-6-yl)phenyl)ethyl)-l,3-oxazinan-2-oneTo a solution of 6-bromo-2-methyl-[l,2,4]triazolo[l,5-a]pyridine (9.5 mg, 0.045 mmol) in DME (3 mL) was added Pd(PPh3)4 (5.2 mg, 0.0045 mmol) under N2. After being stirred at room temperature for 1 hour, the mixture was added a solution of (2^-6- (2-hydroxy-2-methylpropyl)-6-isopropyl-3-(f5>;l-(4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)phenyl)ethyl)-l,3-oxazinan-2-one (20 mg, 0.045 mmol) in ethanol (1.5 mL) and saturated NaHCO3 solution(l mL). The mixture was heated to reflux for 2 hours under N2. The reaction mixture was treated with ethyl acetate (10 mL) and water (10 mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by preparative HPLC to give f5^-6-(2-hydroxy- 2-methylpropyl)-6-isopropyl-3-(5y)- 1 -(4-(2-methyl-[ 1 ,2,4]triazolo[ 1 ,5-a]pyridin-6-yl) phenyl)ethyl)-l,3-oxazinan-2-one (6.00 mg, 30%). LC-MS Method 2 tR = 0.99 min, m/z = 451. 1H NMR (CD3OD): 0.90 (d, 3H), 1.00 (d, 3H), 1.33 (d, 6H), 1.65 (d, 3H), 1.78 (d, IH), 1.93 (m, 2H), 2.17 (m, IH), 2.28 (m, IH), 2.58 (s, 3H), 2.84 (m, IH), 3.39 (m, IH), 5.73 (q, IH), 7.52 (d, 2H), 7.76 (m, 3H), 8.01 (d, IH), 8.99 (s, IH). (S)-6-(2-hydroxy-2-methylpropyl)-6-isopropyl-3-((S)-l-(4-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)phenyl)ethyl)-l,3-oxazinan-2-one was prepared as described in WO 2009/134400 Example 17.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7169-95-1, its application will become more common.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; CLAREMON, David, A.; WO2010/91067; (2010); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem