Pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 13959-02-9, 3-Bromoisonicotinic 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, 13959-02-9, blongs to pyridine-derivatives compound. Quality Control of 3-Bromoisonicotinic acid

General procedure: To a solution of Intermediate 7 (110 mg, 0.37 mmol), 3-methoxybenzene-1,2- diamine (50 mg, 0.34 mmol) and DIPEA (0.2 mL, 1 mmol) in DMF (2 mL) was added HATU (160 mg, 0.41 mmol). The reaction mixture was stirred at r.t. for 48 h, then partitioned between DCM and water. The organic phase was separated, then dried and concentrated in vacuo. The crude residue was purified by flash column chromatography (0-100% EtOAc/hexanes) to give the title compound (28.7 mg, 20%) as a white solid. LCMS (Method 5): [M+H]+ m/z 415, RT 1.31 minutes.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13959-02-9, its application will become more common.

Reference:
Patent; UCB BIOPHARMA SPRL; BRACE, Gareth Neil; CHAPPELL, Rose Elizabeth; FOULKES, Gregory; FROST, James Richard; HORSLEY, Helen Tracey; JONES, Elizabeth Pearl; LECOMTE, Fabien Claude; REUBERSON, James Thomas; SCHULZE, Monika-Sarah Elisabeth Dorothea; TAYLOR, Richard David; YAU, Wei Tsung; ZHU, Zhaoning; (246 pag.)WO2019/138017; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 884494-73-9 ,Some common heterocyclic compound, 884494-73-9, molecular formula is C7H6FNO2, 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.

General procedure: A solution of 4-(6-(3 ,6-diazabicyclo[3. 1.1 ]heptan-3 -yl)pyridin-3 -yl)-6-(2- hydroxy-2-methylpropoxy)pyrazolo[ 1,5 -a]pyridine-3 -carbonitrile dihydrochloride (Intermediate P43; 30mg, 0.063 mmol), in DCM (1 mL) was treated with DIEA (27 tL, 0.16 mmol) and stirred for 5 mm at ambient temperature. The resulting mixture was treated sequentially with 5-chloro- 6-methoxynicotinaldehyde (11 mg, 0.063 mmol) and NaBH(AcO)3 (27 mg, 0.13 mmol). After stirring 12 h at ambient temperature, the reaction mixture was diluted with DCM and washed with 10% Na2CO3(aq). The combined organic extracts were dried over anhydrous MgSO4(), filtered, and concentrated in vacuo. The residue was purified by silica chromatography (10% MeOHI DCM with 1% NH4OH as the eluent) to cleanly provide the title compound (22 mg, 63% yield). MS (apci) m/z = 560.3 (M+H).

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. 884494-73-9, 5-Fluoro-6-methoxynicotinaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ANDREWS, Steven W.; ARONOW, Sean; BLAKE, James F.; BRANDHUBER, Barbara J.; COOK, Adam; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; MCFADDIN, Elizabeth A.; MCKENNEY, Megan L.; MCNULTY, Oren T.; METCALF, Andrew T.; MORENO, David A.; TANG, Tony P.; REN, Li; (668 pag.)WO2018/71447; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 63071-13-6, 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.63071-13-6, name is 4-Chloropicolinaldehyde, molecular formula is C6H4ClNO, molecular weight is 141.56, as common compound, the synthetic route is as follows.

Step 1. Preparation of 4-(2-((1R,2R)-2-hydroxycyclohexylamino)benzo[d]thiazol-6-yloxy)picolinaldehyde To the reaction mixture of 2-((1R,2R)-2-hydroxycyclohexylamino)benzo[d]thiazol-6-ol (90 mg, 0.34 mmol) in 1.9 ml of NMP was added Cesium Carbonate (232 mg, 0.71 mmol) and 4-chloropicolinaldehyde (125 mg, 0.883 mmol). The reaction mixture was stirred at RT. for 10 minutes and then microwaved at 150 C. for 750 seconds. The crude reaction mixture was filtered, purified on prep HPLC and lyophilized to give 4-(2-((1R,2R)-2-hydroxycyclohexylamino)benzo[d]thiazol-6-yloxy)picolinaldehyde as TFA salt (88 mg). ES/MS m/z 388.1 (MH+) as the hydrate (+18).

The chemical industry reduces the impact on the environment during synthesis 63071-13-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Novartis AG; US2008/45528; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 13959-02-9, 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 13959-02-9, name is 3-Bromoisonicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 33methyl 3-bromoisonicotinate H2SO4 (0.5 mL) was added to a solution of 3-bromoisonicotinic acid (500 mg, 2.48 mmol) in MeOH (10 mL). The resulting solution was heated at reflux overnight. The mixture was cooled to 0° C. and a solution of 5percent NaHCO3 (5 mL) was added. The aqueous layer was basified to pH=7-8 with 50percent aqueous NaOH. It was then extracted with DCM (3.x.). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to afford title crude product (465 mg, 87percent) as an oil. 1H NMR (300 MHz, CDCl3) delta ppm 3.96 (s, 3H) 7.61 (d, J=5.10 Hz, 1H) 8.61 (d, J=5.10 Hz, 1H) 8.85 (s, 1H).

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 13959-02-9, 3-Bromoisonicotinic acid.

Reference:
Patent; ASTRAZENECA AB; US2010/130477; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 62068-78-4, 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. 62068-78-4, name is 2,6-Dichloronicotinamide, molecular formula is C6H4Cl2N2O, 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.

6-Chloro-2-(2-methoxy-ethylamino)-nicotinamide (2) (1113) Refer to synthesis of D46 for preparation of 2,6-dichloro-nicotinamide (1). A sealed reaction vessel containing 2,6-dichloro-nicotinamide (1) (8.66 g, 45.3 mmol) and 2-methoxy-ethylamine (15.6 mL, 181 mmol) in anhydrous dimethylformamide (40 mL) was heated to 60 C. for 7 h. The reaction was then cooled to room temperature. Dimethylformamide was azeotropically removed by the addition and evaporation of toluene (6×700 mL) by rotary evaporation with water bath at 70 C. An orange oil was obtained (12.2 g). The oil was fractionated by dry-pack column chromatography as follows: the oil was diluted with CH2Cl2 (400 mL) followed by the addition of silica gel (100 g, 230-400 mesh) and concentrated to dryness. This was loaded onto a silica column (200 g, 230-400 mesh) and eluted with 50% EtOAc/hexanes. Pure fractions were combined and concentrated to give the title compound as a white solid (5.37 g, 64% isolated yield). 1H NMR 400 MHz (d6-DMSO) delta7.79 (d, J=7.8 Hz, 1H), 7.30 (s, 1H), 6.76 (d, J=7.8 Hz, 1H), 6.52 (s, 1H), 4.04 (br t, J=4.7 Hz, 1H), 3.80 (td, J=5.5, 4.7 Hz, 2H), 3.63 (t, J=5.5 Hz, 2H), 2.94 (s, 3H).

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 62068-78-4, 2,6-Dichloronicotinamide.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; AKAMA, Tsutomu; US2015/291629; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 65001-21-0, 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.65001-21-0, name is 5-Bromopyridine-3-sulfonyl chloride, molecular formula is C5H3BrClNO2S, molecular weight is 256.51, as common compound, the synthetic route is as follows.

Step 3 – Preparation of 3-[l-(5-bromo pyridine-3-sulfonyl)-5-chloro-lH-indol-3-yl] propionic acid methyl ester (11); [0176] Into a flask, 3-(5-chloro-lH-indol-3-yl)-propionic acid methyl ester (11, 150 mg, 0.00063 mol), and tetrabutyl ammonium hydrogen sulfate were dissolved in 20 mL of dichloromethane and 20 mL of 50% KOH solution was added. The solution was mixed vigorously and 5-bromo- pyridyl-3-sulfonyl chloride (10, 240 mg, 0.00095 mol) was slowly added to the reaction. After 5-6 minutes of vigorous stirring, precipitates began to form. An additional 3-4 mL of 50% KOH was added and the reaction was stirred overnight. TLC (30% ethyl acetate/hexane) showed that the starting material had disappeared. The reaction mixture was extracted with 3 x 50 mL of dichloromethane and the organic layers were combined and washed with water, brine, and dried over MgSO4. The organic layer was filtered and roto evaporated to half its volume. Silica was added and the solvent completely removed. Chromatography was run using a gradient solvent condition of 0 to 20% ethyl acetate/hexane over 15 minutes, then 20 to 45% over 15 minutes. The desired compound was isolated. 1H NMR consistent with structure.

Statistics shows that 65001-21-0 is playing an increasingly important role. we look forward to future research findings about 5-Bromopyridine-3-sulfonyl chloride.

Reference:
Patent; PLEXXIKON, INC.; WO2008/109700; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 13228-40-5, 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. 13228-40-5, name is 2-(2-Pyridyl)indole. A new synthetic method of this compound is introduced below.

Step 3: To a solution of 16 (1.6 g, 8.24 [MMOL) IN ACOH] (30 ml) at 80 [C] was added 4-piperidone hydrochloride (3.7 g, 23.9 [MMOL)] and [H3PO4] (10 [ML).] The reaction was stirred at this temperature for 72 h and at [100] C for 24 h. The reaction was cooled to RT and poured into [ICE/NH40H] and extracted with EtOAc. The combined organic layers were washed with water and brine, dried [(NA2SO4)] and concentrated. The residue was purified on a flash column (20% EtOAc in hexane to 10% CH30H/NH3 in [CH2CI2)] to give 17 (0.5 g, 44% based on recovered starting material). MS (M+H) [=] 276.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13228-40-5, its application will become more common.

Reference:
Patent; SCHERING CORPORATION; WO2004/831; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1035123-89-7, 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. 1035123-89-7, name is 3-(6-Bromopyridin-3-yl)acrylic acid, molecular formula is C8H6BrNO2, 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 3: 3-(6-Bromo-pyridin-3-yl)-N-(3-ethynyl-5-fluoro-4-methanesulfonylamino-benzyl)-acrylamide N-(4-Aminomethyl-2-ethynyl-6-fluoro-phenyl)-methanesulfonamide HCl salt (63 mg, 0.219 mmol) was suspended in THF and treated with triethylamine (25 mg, 0.241 mmol) and then the resulting mixture was stirred for 10mins. 3-(6-Bromo-pyridin-3-yl)-acrylic acid (50 mg, 0.219 mmol) was added to the reaction mixture followed by DMTMM (66 mg, 0.241 mmol) after 10 mins. The resulting mixture was stirred overnight at ambient temperature and then diluted with EtOAc. The resulting solution was washed successively with water, sat’d NaHCO3 (x2), and brine, and then dried over anhyd. Na2SO4, filtered and concentrated under reduced pressure. The crude residue was recrystallized (EtOAc/n-Hexane) to yield the title compound (71 mg, 72 %). 1H NMR (300 MHz, DMSO-d6): delta 9.42 (s, 1H), 8.77 (t, 1H, J = 6.0 Hz), 8.60 (d, 1H, J = 2.4 Hz), 7.96 (dd, 1H, J = 8.1, 1.8 Hz), 7.70 (d, 1H, J = 8.1 Hz), 7.48 (d, 1H, J = 15.9 Hz), 7.28 (s, 1H), 7.27 (d, 1H, J = 8.7 Hz), 6.81 (d, 1H, J = 15.9 Hz), 4.50 (s, 1H), 4.39 (d, 2H, J = 5.7 Hz), 3.06 (s, 3H). ESI [M+H]+; 452.0.

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 1035123-89-7, 3-(6-Bromopyridin-3-yl)acrylic acid.

Reference:
Patent; Amorepacific Corporation; EP1882687; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 16830-24-3 , The common heterocyclic compound, 16830-24-3, name is Methyl 2-methylisonicotinate, molecular formula is C8H9NO2, 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.

The remaining solid is washed with diethyl ether and dried to give methyl 2-methyl-pyridine-4-carboxylate; LC-MS: tR=0.39 min, [M+1]+=152.05. This material is dissolved in 7 N NH3 in methanol (25 mL) and the mixture is stirred in a sealed vial for 20 h at 60 C. before it is filtered. The filtrate is evaporated to give crude 2-methyl-isonicotinamide (2.12 g) as a brownish solid.

The synthetic route of 16830-24-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bolli, Martin; Lescop, Cyrille; Mathys, Boris; Mueller, Claus; Nayler, Oliver; Steiner, Beat; Velker, Jorg; US2011/212998; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 18368-76-8, 2-Chloro 3-methylpyridine, 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, Safety of 2-Chloro 3-methylpyridine, blongs to pyridine-derivatives compound. Safety of 2-Chloro 3-methylpyridine

The compound 5 (1 mmol),The compound 2-chloro-3-methylpyridine (1 mmol)Dissolved in NMP (10 mL)CuI (20 mmolpercent) was added,Pd (PPh3) 2Cl2 (5 mmolpercent),DIEA (5 mmol).Under nitrogen protection,60 reaction 12h.TCL monitoring reaction is complete,Extracted three times with ethyl acetate,Combine organic phase,Washed twice with saturated NaCl,Anhydrous Na2SO4 dry.Spin dry,Column chromatography gave compound 7j.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,18368-76-8, 2-Chloro 3-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; Second Military Medical University, PLA; Yantai Dongcheng Pharmaceutical Industry Group Co., Ltd.; Zhang, Dazhi; Jiang, Yuanying; Niting, Junhong; Cai, Zhan; Pang, Lei; Xie, Fei; Li, Ran; Han, Haibing; He, Yan; You, Shouyi; Yang, Zhenqiu; Qi, Dongqi; (36 pag.)CN106336383; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem