Day: July 29, 2021

Reference of 89284-61-7 , The common heterocyclic compound, 89284-61-7, name is 4-Chloronicotinonitrile, molecular formula is C6H3ClN2, 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.

Intermediate 35 (0.10 g, 0.383 mmol) was dissolved in anhydrous THF (3.99 mL), and 60% wt. in mineral oil) (0.034 g, 0.842 mmol) was added in one portion at 0 C. After 30 4-chloronicotinonitrile (0.133 g, 0.957 mmol) and was added in one portion, and the on mixture was allowed to reach rt overnight (16 h). Afterwards, the reaction mixture was hed with NH4Cl (2 mL), diluted with EtOAc (50 mL), washed with water (2×10 mL), (1×20 mL), dried (Na2SO4), filtered, concentrated, and purified by normal phasematography to give Example 44A (138 mg, 99%). MS (ESI) m/z: 364.1 (M+H)+. Example 44B. Preparation of 4-((aR)-6-aminospiro[3.3]heptan-2- y)nicotinamide NH2

The synthetic route of 89284-61-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SMITH II, Leon M.; LADZIATA, Vladimir; DELUCCA, Indawati; PINTO, Donald, J., P.; ORWAT, Michael J.; DILGER, Andrew K.; PABBISETTY, Kumar Balashanmuga; YANG, Wu; SHAW, Scott A.; GLUNZ, Peter W.; PANDA, Manoranjan; (612 pag.)WO2017/123860; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 866755-20-6, 2,6-Dichloro-3-bromopyridine, 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, SDS of cas: 866755-20-6, blongs to pyridine-derivatives compound. SDS of cas: 866755-20-6

Fresh cut sodium (0.101 g 4.41 mmol) was added to EtOH (50 mL) . The resulting mixture was stirred at rt. After the solid dissolved 3-bromo-2 6-dichloropyridine (1 g 4.41 mmol) was added. The resulting mixture was stirred at 70 overnight. After LCMS analysis showed the starting material was disappeared. The solvent was removed in vacuo. The residue was dissolved in DCM (60 mL) and washed with H2O (20 mL) and brine (20 mL) . The organic layer was dried over Na2SO4 filtered and concentrated. The residue was purified by silica column chromatography (PE/EA 20/1) to yield a white solid of a mixture of 3-bromo-2-chloro-6-ethoxypyridine 3-bromo-2 6-diethoxypyridine and 3-bromo-6-chloro-2-ethoxypyridine (930 mg 3.85 mmol 87yield) 1HNMR(400 MHz CD3OD) delta 7.85 (d J 1.2 Hz 1H) 6.88 (d J 8.0 Hz 1H) 4.42-4.36 (m 2H) 1.39 (t J 7.2 Hz 3H) ES-LCMS m/z 235.9 237.9 (M+H)

The synthetic route of 866755-20-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R & D COMPANY LIMITED; CHEUNG, Mui; DEMARTINO, Michael P.; EIDAM, Hilary Schenck; GUAN, Huiping Amy; QIN, Donghui; WU, Chengde; GONG, Zhen; YANG, Haiying; YU, Haiyu; ZHANG, Zhiliu; (391 pag.)WO2016/37578; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6188-23-4, 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 6188-23-4 as follows.

To a solution of 6-bromoimidazo[1,2-a]pyridine (318 mg, 1.61 mmol) in 1,4-dioxane (15 mL) were added N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)cyclopropanesulfonamide (600 mg, 1.69 mmol), KOAc (316 mg, 3.22 mmol), H2O (3 mL) and Pd(dppf)Cl2.CH2Cl2 (131 mg, 0.161 mmol). The reaction was heated to 85 C. and stirred further for 5 hours under N2 atmosphere, then cooled to rt, and concentrated in vacuo. The residue was dissolved in DCM (200 mL) and the resulted mixture was filtered through a CELITE. The filtrate was washed with H2O (100 mL) and brine (100 mL). The combined aqueous layers were extracted with DCM (50 mL*3). The combined organic extracts were dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by a flash silica gel column chromatography (DCM/MeOH (v/v)=65/1) to give the title compound as a yellowish solid (342 mg, 62%). MS (ESI, pos. ion) m/z: 345.0 [M+H]+; 1H NMR (600 MHz, DMSO-d6): delta 9.42 (s, 1H), 8.91 (s, 1H), 8.35 (d, J=2.1 Hz, 1H), 7.99 (s, 1H), 7.93 (d, J=2.4 Hz, 1H), 7.68-7.61 (m, 2H), 7.54 (dd, J=1.8, 9.6 Hz, 1H), 3.98 (s, 3H), 2.82-2.74 (m, 1H), 1.00-0.89 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6188-23-4, its application will become more common.

Reference:
Patent; Calitor Sciences, LLC; Xi, Ning; US2014/134133; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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