Tag: M.W:200-300

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 884494-81-9, name is 3-Bromo-5-fluoro-2-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C6H5BrFNO

To a solution of 18.0 g (87.4 mmol) of 3-bromo-5-fluoro-2-methoxypyridine in 63 mL of anhydrous THF was added 67.0 mL (87.1 mmol, 1 .3 M in THF) of i-PrMgCI LiCI slowly at 0 C. The mixture was stirred at rt under Ar atmosphere for 4 h.To a stirred solution of 12.6 g (43.6 mmol) of compound 17-1 in 10 mL of DCM was added 130 mL of the above Grignard reagent (-0.4 M in THF) at -78 C. The mixture was stirred at rt under Ar atmosphere overnight, then quenched by addition of 200 mL of saturated NH4CI at 0 C. The organic phase was separated, dried over anhydrous Na2S04. After filtration, the filtrate was concentrated to afford a residue, which was purified by Ci8column eluting with 0 to 30 % gradient of ACN in H20 (0.5 % NH4HCO3) to afford compound 17-2. LC-MS: m/e = 417 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 884494-81-9.

Reference:
Patent; ANGEX PHARMACEUTICAL, INC.; WU, Wen-Lian; YANG, Zhiqiang; LEE, Francis; TAN, John Qiang; (112 pag.)WO2019/94143; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 58584-86-4 ,Some common heterocyclic compound, 58584-86-4, molecular formula is C8H7Cl2NO2, 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 first step of Scheme 5: A dry round bottom flask was charged with NaH (264 mg of a 60% dispersion in mineral oil, 6.6 mmole) and the reagent washed twice with hexane. 5 mL dry DMF was added and benzyl alcohol (0.62 mL, 6.0 mmole) was added dropwise. After H2 evolution had ceased the reaction mixture was added dropwise to a 0 C. solution (10 mL) of 2,6-dichloro-nicotinic acid ethyl ester (1.33 g, 6.0 mmole). It was stirred 15 minutes, and then allowed to stir another 20 minutes at room temperature. The reaction mixture was then poured into 150 mL water and extracted with ether (3×75 mL). Combined organic phases were washed with water, brine and dried over MgSO4. Filtration and evaporation gave the crude product which was then purified by chromatography on silica gel using a gradient of hexane/EtOAc (0 to 4%) as eluent. Pure fractions were combined and evaporated to give 818 mg (47%) of a 1:1 mixture of 2-benzyloxy-6-chloro-nicotinic acid ethyl ester and 6-benzyloxy-2-chloro-nicotinic acid ethyl ester.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,58584-86-4, its application will become more common.

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 14338-32-0, 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. 14338-32-0, name is 2-Chloro-1-methylpyridinium iodide, molecular formula is C6H7ClIN, 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 F: 2-[3-(Pyrrolidine-1-sulfonyl)-phenyl]-pent-4-enoic acid allyl-(1-(S)-phenyl-2-pyrrolidin-1-yl-ethyl)-amide To a stirred solution of allyl-(1-(S)-phenyl-2-pyrrolidin-1-yl-ethyl)-amine (1.00 g, 4.34 mmol) in dichloromethane (22 cm3) at ambient temperature was added 2-[3-(pyrrolidine-1-sulfonyl)-phenyl]-pent-4-enoic acid (1.34 g, 4.34 mmol) followed by 2-Chloro-1-methylpyridinium iodide (2.22 g, 8.68 mmol) and triethylamine (1.82 cm3, 13.0 mmol) to afford a yellow slurry. The mixture was stirred at ambient temperature for 44 hours to afford a brown solution. The solution was diluted with ethyl acetate (50 cm3) and poured into water (100 cm3). The aqueous was extracted with ethyl acetate (3*30 cm3) and the combined ethyl acetate extracts were washed with 1M sodium bicarbonate (2*50 cm3), brine (1*50 cm3), dried over sodium sulfate, vacuum filtered and the volatile fractions removed in vacuo to a crude brown oil. The crude product was purified by column chromatography (silica, eluding with dichloromethane-methanol 99:1 to 95:5 to afford the title compound as a tan viscous oil (2.10, 92.9%) with a positive ion ESI (M+H) +522.3.

According to the analysis of related databases, 14338-32-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dolle, Roland E.; Tuthill, Paul Anson; US2004/209857; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 871826-12-9, (5-(Trifluoromethyl)pyridin-2-yl)methanamine hydrochloride, 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, 871826-12-9, blongs to pyridine-derivatives compound. name: (5-(Trifluoromethyl)pyridin-2-yl)methanamine hydrochloride

General procedure: The carboxylic acid 8 is dissolved in DMF and 2 eq. of the corresponding amine component, 1.5 eq. of HATU and 3 eq. of triethylamine are added. The reaction mixture is stirred at rt until TLC and/or LCMS indicate complete consumption of the starting material (2 h), then water is added. The formed precipitate is filtered off, washed with water and dried in a vacuum drying cabinet at 40C. If appropriate, the product is purified by preparative HPLC.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,871826-12-9, its application will become more common.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; PANKNIN, Olaf; BAeURLE, Stefan; RING, Sven; SCHWEDE, Wolfgang; BONE, Wilhelm; NOWAK-REPPEL, Katrin; BENDER, Eckhard; NUBBEMEYER, Reinhard; GNOTH, Mark, Jean; WO2013/107743; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 505084-59-3, 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.505084-59-3, name is 2-Chloro-5-(trifluoromethyl)nicotinic acid, molecular formula is C7H3ClF3NO2, molecular weight is 225.55, as common compound, the synthetic route is as follows.

To a stirred solution of 478 2-chloro-5-(trifluoromethyl)pyridine-3-carboxylic acid (2 g, 8.87 mmol) in 45 THF (5 mL) and 139 MeOH (5 mL) was added 479 (trimethylsilyl)diazomethane (8.87 mL, 17.73 mmol) (2 M in 123 hexane) dropwise at -20 C. and the reaction was stirred at -20 C. for 2 h. The solvent was concentrated under reduced pressure and the residue was purified by flash silica gel chromatography to afford the 480 title compound as an oil. MS (ESI) m/z: 242.2 [M+H+]

The chemical industry reduces the impact on the environment during synthesis 505084-59-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Merck Sharp & Dohme Corp.; Han, Yongxin; Achab, Abdelghani; Deng, Yongqi; Fradera, Xavier; Gibeau, Craig; Hopkins, Brett A.; Li, Derun; Liu, Kun; McGowan, Meredeth A.; Sciammetta, Nunzio; Sloman, David; White, Catherine; Zhang, Hongjun; Zhou, Hua; US2019/144433; (2019); A1;,
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 65515-28-8, name is Methyl 2,6-dichloronicotinate. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C7H5Cl2NO2

[Example 24] Synthesis of 2-chloro-6-phenyl-nicotinic acid methyl ester To the mixture of 2,6-dichloro-nicotinic acid methyl ester (4.0 g, 19 mmol) synthesised in Example 23 and tetrahydrofuran (39 ml), phenyl boronic acid (2.5 g, 19 mmol), potassium carbonate (8.0 g, 58 mmol), and tetrakis(triphenylphosphine)palladium(0) (1.2 g, 0.97 mmol) were added, and the obtained reaction mixture was stirred for 16 hours while being heated to reflux. The reaction mixture was cooled to room temperature, and then insoluble matter was removed by filtration. The solvents were evaporated under reduced pressure from the filtrate, and then water and ethyl acetate were added to the obtained residue, followed by extraction. The organic layer and the aqueous layer were separated, and the aqueous layer was further extracted using ethyl acetate. The organic layers were mixed, washed with saturated saline, and dried using anhydrous sodium sulfate. The solvents were evaporated under reduced pressure, and the obtained residue was purified with silica gel column chromatography (heptane: ethyl acetate = 10:1 to 3:1). The obtained crude compound was recrystallized using the mixed solvent of heptane-diethyl ether, thereby obtaining the entitled compound (2.2 g, 47%). 1H-NMR Spectrum (CDCl3) delta(ppm): 3.98(3H, s), 7.46-7.53(3H, m), 7.74(1H, d, J=8.0Hz), 8.04-8.08(2H, m), 8.25(1H, d, J=8.0Hz)

With the rapid development of chemical substances, we look forward to future research findings about 65515-28-8.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP2062901; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 866755-20-6, 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. 866755-20-6, name is 2,6-Dichloro-3-bromopyridine, molecular formula is C5H2BrCl2N, 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.

To a mixture of 3-bromo-2,6-dichloropyridine (4.5 g, 20 mmol ) and tert-butyl ((l S,3S)-3-hydroxycyclobutyl)carbamate (see PREPARATION 4A; 3.65 g, 20 mmol) in acetonitrile (50 mL) was added CS2CO (13.2 g, 40 mmol), and then the mixture was stirred at RT overnight. The reaction mixture was filtered and concentrated under vacuum to give tert- butyl ((l S,3S)-3-((3-bromo-6-chloropyridin-2-yl)oxy)cyclobutyl)carbamate (4.2 g, 11.2 mmol, 56%). ESI-MS (M+1): 377 calc. for Ci4Hi8BrClN203 376.

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 866755-20-6, 2,6-Dichloro-3-bromopyridine.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer; FROHN, Michael; HARRINGTON, Paul; PICKRELL, Alexander; RZASA, Robert; SHAM, Kelvin; HU, Essa; WO2011/143366; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6311-35-9, 6-Bromonicotinic 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: C6H4BrNO2, blongs to pyridine-derivatives compound. COA of Formula: C6H4BrNO2

Step 1: 6-Chloronicotinamide To a solution of 6-bromopyridine-3-carboxylic acid (50 g, 247 mmol) in DCM (1 L) and DMF (3 mL) at room temperature was dropwise added oxalyl dichloride (80 mL). The mixture was stirred for 30 min at room temperature. The solvent was removed under reduced pressure and ammonia (1 L, 25-28% aqueous solution) was added dropwise. The resulting mixture was stirred for a further 1 h at room temperature. The solvent was evaporated in vacuo to yield 43 g of the crude product, which was used directly in the next step without further purification. LCMS (ESI): [M+H]+=157/159.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6311-35-9, 6-Bromonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; Genentech, Inc.; Braun, Marie-Gabrielle; Garland, Keira; Hanan, Emily; Purkey, Hans; Staben, Steven T.; Heald, Robert Andrew; Knight, Jamie; Macleod, Calum; Lu, Aijun; Wu, Guosheng; Yeap, Siew Kuen; (183 pag.)US2018/65983; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 78686-79-0 ,Some common heterocyclic compound, 78686-79-0, molecular formula is C7H5BrClNO2, 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.

Compound WX069-1 (7.00 g, 27.95 nmol) wasdissolved in dimethyl sulfoxide solution (50.00 mE) at roomtemperature, followed by the addition of cesium fluoride(8.00 g, 52.67 mmol) at room temperature. The reactionmixture was heated to 550 C. and stirred for 14 hours. Afterthe reaction, the mixture was cooled to room temperature,quenched with saturated brine (10 mE), diluted with water(50 mE) and extracted with ethyl acetate (20 mLx3). Thecolunm c1omatography (eluent: petroleum ether/ethylorganic phases were separated, washed with water (50mEx2) and dried over anhydrous sodium sulfate, followedby filtration. The filtrate was concentrated under reducedpressure. The obtained residue was isolated by silica gelacetate1 00/1 – 100/15, volume ratio) to obtain the targetproduct WX069-2. ?H NMR (400 MHz, CDC13) oe: 8.64-8.31 (m, 2H), 3.98 (s, 3H).

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. 78686-79-0, Methyl 5-bromo-2-chloronicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SHIJIAZHUANG SAGACITY NEW DRUG DEVELOPMENT CO., LTD.; LUO, Yunfu; YANG, Chundao; LEI, Maoyi; LIU, LING; HU, Guoping; LI, Jian; CHEN, Shuhui; US2019/177318; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 944317-53-7, 4-Methyl-5-nitro-2-(trifluoromethyl)pyridine, 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: C7H5F3N2O2, blongs to pyridine-derivatives compound. COA of Formula: C7H5F3N2O2

Into a 1L 3-necked round-bottom flask was placed 4-methyl-5-nitro-2- (trifluoromethyl)pyridine (60 g, 291.26 mmol, 1 equiv), Fe (48.9 g, 873.79 mmol, 3 equiv), NH4CI (77.2 g, 1456.31 mmol, 5 equiv), and H2O (500 mL). The resulting mixture was stirred for 2 at 80 C. The resulting solution was extracted with ethyl acetate. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1/10) to give (27 g, 60.76%) of the title compound as a white solid. LC-MS: (ES, m/z): [M+H]+ 177.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,944317-53-7, 4-Methyl-5-nitro-2-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; IDEAYA BIOSCIENCES, INC.; ALAM, Muzaffar; BECK, Hilary, Plake; DILLON, Michael, Patrick; GONZALEZ-LOPEZ, Marcos; SUTTON, James, Clifford, Jr.; (248 pag.)WO2019/156987; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem