Tag: M.W:100-200

Electric Literature of 16665-38-6 ,Some common heterocyclic compound, 16665-38-6, molecular formula is C7H9NO2, 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.

4-Methoxypyridine-2-carbaldehyde, used as starting material was prepared as follows:- Manganese(IV) oxide (2.412 mL, 139.42 mmol, 4eq) was added portionwise to (4- methoxypyridin-2-yl)methanol (4.85g, 34.85 mmol, leq) in ethyl acetate (15OmL). The resulting mixture was stirred at 80 0C for 2 h. The hot reaction mixture was filtered through celite. The resulting mixture was evaporated to dryness to afford desired A- methoxypyridine-2-carbaldehyde (3.01 g, 21.93 mmol, 62.9 percent). IH NMR (400.132 MHz, DMSO) delta 3.93 (3H, s), 7.27 (IH, m), 7.44 (IH, d), 8.63 (IH, d), 9.96 (IH, s)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16665-38-6, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/56886; (2009); 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. 6332-56-5, name is 3-Nitropyridin-2(1H)-one. A new synthetic method of this compound is introduced below., Recommanded Product: 3-Nitropyridin-2(1H)-one

Example 97A methyl 4-(3-nitro-2-oxopyridin-1(2H)-yl)benzoate A mixture of 2-hydroxy-3-nitropyridine (1.168 g, 8.33 mmol), copper (II) acetate (2.271 g, 12.50 mmol), 4-methoxycarbonylphenylboronic acid (3 g, 16.67 mmol) and pyridine (10.11 mL, 125 mmol) was stirred under N2 for 5 minutes, and the atmosphere (balloon) was changed to O2. The mixture was then stirred at 90 C. overnight. The mixture was cooled to room temperature, treated with water (50 mL) and stirred for 5 minutes. The solid was collected by filtration, washed with water, and dried under vacuum. The solid was chromatographed on silica gel eluting with a gradient of 0-100% ethyl acetate in [9:1 CH2Cl2:ethyl acetate] to provide the title compound (1.57 g, 5.73 mmol, 68.7% yield). 1H NMR (400 MHz, DMSO-d6) delta 8.53 (dd, J=7.7, 2.0 Hz, 1H), 8.20 (dd, J=6.7, 2.0 Hz, 1H), 8.12 (d, J=8.5 Hz, 2H), 7.67 (d, J=8.5 Hz, 2H), 6.58-6.53 (m, 1H), 3.90 (s, 3H); MS (ESI+) m/z 275 (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, 6332-56-5, 3-Nitropyridin-2(1H)-one.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Cowart, Marlon D.; Esmieu, William Ramesh; Gfesser, Gregory A.; Greszler, Stephen N.; Koenig, John R.; Kym, Philip R.; Liu, Bo; Malagu, Karine Fabienne; Patel, Sachin V.; Scanio, Marc J.; Searle, Xenia B.; Voight, Eric; Wang, Xeuqing; Yeung, Ming C.; (202 pag.)US2017/15675; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 571189-49-6, 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 571189-49-6, name is 5-(4-Methylpiperazin-1-yl)pyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

5-(6-[[5-(4-methylpiperazin-l-yl)pyridin-2-yl]amino]pyrimidin-4-yl)-2-(oxan-4- yloxy)benzonitrile: 5-(6-[[5-(4-methylpiperazin- l-yl)pyridin-2-yl]amino]pyrimidin-4-yl)-2- (oxan-4-yloxy)benzonitrile was prepared from 5-(6-chloropyrimidin-4-yl)-2-(oxan-4- yloxy)benzonitrile and 5-(4-methylpiperazin-l-yl)pyridin-2-amine using Method 28. The final product was purified by prep-HPLC under the following conditions: column, XB ridge Prep C18 OBD Column, 150 x 19 mm, 5 um; mobile phase, acetonitrile in water (with 0.05% NH3.H20), 30% to 60% gradient in 8 min; detector, UV 254 nm. 5-(6-[[5-(4-methylpiperazin- l-yl)pyridin- 2-yl]amino]pyrimidin-4-yl)-2-(oxan-4-yloxy)benzonitrile was obtained as light yellow solid (59 mg, 44% for 2 steps). HPLC: 98.1% purity, RT = 2.51 min. MS: m/z = 472.3 [M+H]+. lH NMR (400 MHz, DMSO-/delta) delta 10.01 (s, 1 H), 8.69 (s, 1 H), 8.34-8.21 (m, 2 H), 8.04-8.01 (m, 2 H), 7.99 (s, 1 H), 7.70-7.63 (m, 1 H), 7.55-7.48 (m, 1 H), 7.48-7.40 (m, 1 H), 4.96-4.85 (m, 1 H), 3.91-3.81 (m, 2 H), 3.59-3.48 (m, 2 H), 3.15-3.08 (m, 4 H), 2.49-2.41 (m, 4 H), 2.21 (s, 3 H), 2.10- 1.95 (m, 2 H), 1.74- 1.61 (m, 2 H). Example 30: 6-([6-[3-cyano-4-(oxan-4-yloxy)phenyl]pyrimidin-4-yl]amino)-N,N- dimethylpyridine-3-carboxamide

According to the analysis of related databases, 571189-49-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK PATENT GMBH; KARRA, Srinivasa R.; XIAO, YuFang; SHERER, Brian A.; CHEKLER, Eugene; (163 pag.)WO2019/79375; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 55934-02-6, 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.55934-02-6, name is 2,3,4-Trichloropyridine, molecular formula is C5H2Cl3N, molecular weight is 182.4351, as common compound, the synthetic route is as follows.

The mixture of /er/-butyl /V-[(/er/-butoxy)carbonyl]-/V-(T-{3-hydroxy-l-[(4- methoxyphenyl )m ethyl ]- l//-pyrazolo[3,4-/>]pyrazin-6-yl }- 1 ,3-dihydrospiro[indene-2,4′- piperidin]-3-yl)carbamate (500 mg, 80% purity, 609 pmol, Intermediate BV), 2,3,4- trichloropyridine (133 mg, 730 pmol) and Cs2C03 (593 mg, 1.82 mmol) in DMF (5 mL) was stirred at 100 C for 24 hours. The mixture was diluted with H20 (20 mL), and extracted with EtOAc (20 mL x 2). The combined organic layers were washed with brine (20 mL), dried over anhydrous Na2S04, filtered and concentrated under reduced pressure to afford the residue. The residue was purified by column chromatography (petroleum ether / ethyl acetate = 1 : 0 ~ 3 : 1) to afford /er/-butyl /V-(l’-{3-[(2,3-dichloropyridin-4-yl)oxy]-l-[(4- methoxyphenyl )m ethyl ]- l //-pyrazolo[3,4-/>]pyrazin-6-yl }- 1 ,3-dihydrospiro[indene-2,4′- piperidin]-3-yl)carbamate (160 mg, 37% yield) as a yellow solid. LCMS m/z [M+H]+ = 702.2.

The chemical industry reduces the impact on the environment during synthesis 55934-02-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; TAYLOR, Alexander, M.; LESCARBEAU, Andre; KELLEY, Elizabeth, H.; SHORTSLEEVES, Kelley, C.; WALTERS, W., Patrick; MURCKO, Mark, Andrew; MCLEAN, Thomas, H.; GUNAYDIN, Hakan; GIORDANETTO, Fabrizio; THERRIEN, Eric; (607 pag.)WO2019/183367; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 18677-48-0, 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. 18677-48-0, name is 3,5-Dimethoxypyridine, molecular formula is C7H9NO2, 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.

3,5-dimethoxypyridine of structure 1 (1.4 g, 10 mmol, 1.0 equiv.) was dissolved in tetrahydrofuran(30 mL), cooled to -78 C, add n-butyllithium (n-BuLi) (2.5M n-hexane solution, 4.8mL, 12mmol, 1.2equiv.), Stir for five minutes and add 1,1,2,2-tetrabromoethane (1.75 mL, 15 mmol, 1.5 equiv.). Return to room temperature. Post-processing, purification by silica gel column gave 1.14 g of 4-bromo-3,5-dimethoxypyridine 2 in a yield of 52%.

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 18677-48-0, 3,5-Dimethoxypyridine.

Reference:
Patent; Chongqing University; Li Yang; Chen Di; (11 pag.)CN109836446; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 866546-07-8 ,Some common heterocyclic compound, 866546-07-8, molecular formula is C7H5ClN2, 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: In a microwave reaction vial with a magnetic stirring bar was placed the azaindoleor indole (0.38 mmol), aldehyde (0.19 mmol), and K2CO3 (176 mg, 1.27 mmol), followedby addition of 2.5 mL of 1:1 mixture of MeOH:H2O. The resulting mixture was placed ina microwave reactor and irradiated at 130 oC for 30 minutes. After cooling to roomtemperature, the volatiles were removed under reduced pressure. The crude residue wasdiluted with water (10 mL) and extracted with ethyl acetate (3 x 10 mL). The combinedorganic layers were dried over sodium sulfate, filtered, and the resulting filtrate evaporated in vacuo to give a crude solid that was purified using reversed-phase HPLC,eluting with MeCN/H2O with a trace of TFA to give the desired compound.

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. 866546-07-8, 5-Chloro-1H-pyrrolo[2,3-b]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Uddin, Md. Imam; Buck, Jason R.; Schulte, Michael L.; Tang, Dewei; Saleh, Samir A.; Cheung, Yiu-Yin; Harp, Joel; Manning, H. Charles; Tetrahedron Letters; vol. 55; 1; (2014); p. 169 – 173;,
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. 771579-27-2, name is 3-(Aminomethyl)-4,6-dimethylpyridin-2(1H)-one. A new synthetic method of this compound is introduced below., Quality Control of 3-(Aminomethyl)-4,6-dimethylpyridin-2(1H)-one

[01709] The above acid (0.47 g, 1 .52 mmol) was then dissolved in DMSO (5 mL) and 3- (amino methyl)-4, 6-dimethylpyridin-2( l H)-one (0.462 g, 3.04 mmol) was added.. The reaction mixture was stirred at room temperature for 15 min before PYBOP (1 .18 g, 2.28 mmol) was added to it and stirring was continued overnight. After completion of the reaction, reaction mass was poured into ice to obtain a solid which was filtered and dried to afford the title compound (0.40 g, 59%). LCMS: 444.25 (M + 1 )+; HPLC: 96.85% ((at) 254 nm) (R,;6.3 10; Method: Column: YMC ODS-A 150 mm x 4.6 mm x 5 mu; Mobile Phase: A; 0.05% TFA in water/ B; 0.05% TFA in acetonitrile; Jnj. Vol: 10 mu, Col. Temp.: 30 C; Flow rate: 1 .4 mL/min.; Gradient: 5% B to 95% B in 8 min, Hold for 1 .5 min, 9.5 1 – 12 min 5% B); NMR (DMSO-Patent; EPIZYME, INC.; EISAI CO., LTD.; KUNTZ, Kevin, Wayne; CHESWORTH, Richard; DUNCAN, Kenneth, William; KEILHACK, Heike; WARHOLIC, Natalie; KLAUS, Christine; ZHENG, Wanjun; WO2012/142513; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 183208-35-7, 5-Bromo-1H-pyrrolo[2,3-b]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, 183208-35-7, blongs to pyridine-derivatives compound. Recommanded Product: 5-Bromo-1H-pyrrolo[2,3-b]pyridine

The 5-bromo-7-azaindole 27 (0.5 g, 2.54 mmol), bis (pinacolato) diboron (0. 968 g, 3. 81 mmol), potassium acetate (0.748 g, 7.61 MMOL), [1,1′- bis (diphenylphosphino) ferrocene] dichloropalladium (II) complex with CH2C12 (1: 1) (49 mg, 0.06 mmol) and DMF (11 ML) were heated in a sealed tube at 80 C. After 44 h, the reaction mixture was allowed to cool to room temperature, diluted with EtOAc and saturated brine, and partitioned. The aqueous layer was extracted with EtOAc (3X). The combined organic extracts were washed with brine (LX), dried (MgSO4), filtered and concentrated in vacuo. The crude pinacol ester 44 was used directly for the next step without any further PURIFICATION. 1H NMR (400 MHz; CDC13) 8 1. 38 (s, 12H), 6.51 (d, J= 3.5 Hz, 1H), 7.32 (d, J= 3.5 Hz, 1H), 8. 42 (d, J= 1.2 Hz, 1H), 8. 63 (d, J= 1.2 Hz, 1H) and 10.59 (brs, NH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,183208-35-7, its application will become more common.

Reference:
Patent; EISAI LONDON RESEARCH LABORATORIES LIMITED; WO2004/78757; (2004); A2;,
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. 69950-65-8, name is Methyl 6-formyl-2-pyridinecarboxylate, molecular formula is C8H7NO3, 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 Methyl 6-formyl-2-pyridinecarboxylate

To a solution of methyl 6-formylpicolinate (165 mg, 0.999 mmol) in THF (5 mL) was added dropwise phenylmagnesium chloride (0.6 mL, 1.2 mmol, 2 M in THF) at -78 C. The reaction mixture was stirred at -78 C for 5 min, and then room temperature for 10 min. The reaction was quenched by the addition of saturated aqueous ammonium chloride, and then extracted with ethyl acetate. The conbined organic layer was washed with brine, and dried over Na2SO4. The mixture was concentrated in vacuo. The crude material was purified by flash column chromatography on silica gel (Hexane:AcOEt = 1:1) to give 8e as a slightly yellow oil (120 mg, 49%). 1H NMR (400 MHz, CDCl3) delta 4.01 (3H, s), 5.11 (1H, d, J = 2.4 Hz), 5.85 (1H, d, J = 2.4 Hz), 7.26-7.42 (6H, m), 7.76 (1H, t, J = 7.3 Hz), 8.02 (1H, d, J = 7.3 Hz). 13C NMR (100 MHz, CDCl3) delta 52.8, 75.1, 123.9, 124.8, 127.1, 128.0, 128.6, 137.8, 142.5, 146.3, 161.5, 165.4. IR (ATR) nmax 3414, 3063, 3030, 2952, 1722, 1588, 1494, 1438, 1286, 1193, 1135, 1051 cm-1. MS (ESI) 244 (M+H)+. HRMS (ESI) calcd for C14H14NO3 (M+H)+ 244.09737, found 244.09731.

With the rapid development of chemical substances, we look forward to future research findings about 69950-65-8.

Reference:
Article; Nishigaya, Yosuke; Umei, Kentaro; Watanabe, Daisuke; Kohno, Yasushi; Seto, Shigeki; Tetrahedron; vol. 72; 12; (2016); p. 1566 – 1572;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 128071-75-0, 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. 128071-75-0, name is 2-Bromonicotinaldehyde, molecular formula is C6H4BrNO, 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 40 mL vial was charged with 6 mL of 1,4-dioxane and a stir bar. The mixture was degassed with nitrogen for 5 minutes. The vial was charged with 2-bromonicotinaldehyde (240 mg, 1.290 mmol), cyclopropylboronic acid (222 mg, 2.58 mmol), and cesium fluoride (588 mg, 3.87 mmol). The vial was degassed again with nitrogen. PdCl2dppf (53.1 mg, 0.065 mmol) was added and the reaction mixture was heated to 100 C. under nitrogen. Upon reaction completion, the mixture was cooled to room temperature. Ethyl acetate (30 mL) was added, and the mixture was stirred for 5 minutes, filtered over a pad of silica gel with ethyl acetate, concentrated, and purified via flash column chromatography (0 to 20% ethyl acetate in heptanes) to provide 2-cyclopropylnicotinaldehyde (170 mg, 1.155 mmol, 90% yield). 1H NMR (501 MHz, DMSO-d6) delta ppm 10.40 (s, 1H), 8.61 (dd, J=4.7, 1.8 Hz, 1H), 8.10 (dd, J=7.8, 1.9 Hz, 1H), 7.33 (dd, J=7.9, 4.8 Hz, 1H), 3.08 (tt, J=8.0, 4.7 Hz, 1H), 1.18-0.90 (m, 4H); MS (ESI+) m/z 148.0 (M+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 128071-75-0, 2-Bromonicotinaldehyde.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Couty, Sylvain; De Lemos, Elsa; Desroy, Nicolas; Duthion, Beranger; Gfesser, Gregory A.; Greszler, Stephen N.; Housseman, Christopher Gaetan; Koenig, John R.; Kym, Philip R.; Liu, Bo; Scanio, Marc J.; Searle, Xenia; Wang, Xueqing; Yeung, Ming C.; Zhao, Gang; (263 pag.)US2018/99931; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem