Tag: M.W:100-200

Synthetic Route of 66521-66-2, 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. 66521-66-2, name is 4-(Pyridin-3-yl)pyrimidin-2-amine, molecular formula is C9H8N4, 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 solution under nitrogen gas of 2-(3-methyl-4-bromobenzylamino)-3-cyano-4-(4-tert- butylaminopiperidin-1-yl)quinoline (190 mg, 0.376 mmol) in toluene (10 ml) was added 4-(pyridin- 3-yl)pyrimidin-2-amine (71 mg, 0.413 mmol) and t-BuONa (72 mg, 0.752 mmol). The resulting mixture was degassed 10 min with Argon gas, then Xantphos (21 mg, 0.0376 mmol) and Pd2(dba)3 (34 mg, 0.0376 mmol) were added and the reaction mixture was stirred at 100 °C for 1 h. The reaction mixture was then cooled to room temperature, filtered and concentrated under reduced pressure. The residue was partitioned between brine and EtOAc and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to give yellow oil. The crude compound which upon purification by flash chromatography using (silica-gel: 100-200 mesh, MeOH?CHCl3; 0:100? 20:80) gave 60 mg (yield 26percent) of an pale-yellow solid corresponding to 2-[4-(4-(pyridin-3- yl)pyrimidin-2-ylamino)-3-methylbenzylamino]-3-cyano-4-(4-tert-butylaminopiperidin-1- yl)quinoline. Mass:(ES+) C36H39N9 required 597; found 598 [M+H], HPLC/MS method 6

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 66521-66-2, 4-(Pyridin-3-yl)pyrimidin-2-amine.

Reference:
Patent; GENOSCIENCE PHARMA; BRUN, Sonia; BERET, Antoine; BASSISSI, Firas; HALFON, Philippe; COURCAMBECK, Jerome; (275 pag.)WO2017/191599; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 71690-05-6, 2,3-Dichloro-5-formylpyridine, 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, Formula: C6H3Cl2NO, blongs to pyridine-derivatives compound. Formula: C6H3Cl2NO

To a stirred slurry of methyltriphenylphosphonium bromide (10.0 g) in toluene (200 mL) at 0 C. was added potassium t-butoxide (3.07 g) portionwise to produce a yellow slurry. After 1 hr, the reaction mixture was cooled to -20 C. and 4 (4.0 grams, 22.72 mmol) dissolved in tetrahydrofuran (6 mL) was added dropwise to produce a purple colored slurry. The reaction mixture was heated to 0 C. and stirred for an additional 1 hr. Then the reaction mixture was treated with saturated aqueous brine (150 mL) and diluted with ethyl acetate (200 mL). The resulting organic portion was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting product was chromatographed by silica gel chromatography column eluting with a gradient of ethyl acetate (0%-10%)/hexanes to provide 2.77 g of 1 (70% yield). 1H NMR (400 MHz, CDCl3) delta 8:30 (1H, d, J=2.19 Hz), 7.80 (1H, d, J=2.19 Hz), 6.63 (1H, dd, J=10.96, 17.80 Hz), 5.86 (1H, d, J=17.80 Hz), 5.45 (1H, d, J=10.96 Hz). LC/MS (M+1): 174.

The synthetic route of 71690-05-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tafesse, Laykea; US2010/120862; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 16179-97-8, 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. 16179-97-8, name is 2-(Pyridin-2-yl)acetic acid hydrochloride, molecular formula is C7H8ClNO2, 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.

S2 was prepared analogously to a published procedure.13 2.00 g S1 (11.5 mmol, 1.00 equiv.) and 14 mL MeOH were added to a round-bottom flask. The solution was cooled to 0 C, and 2.90 mL TMSCl (23.0 mmol, 2.00 equiv.) were added dropwise. The mixture was allowed to warm to room temperature and stirred overnight. The solvent was then removed in vacuo, ant the remaining solid was treated slowly with sat. aq. NaHCO3 (40 mL). The aqueous solution was extracted with CH2Cl2 (4 x 40 mL), and the combined organic extracts were dried over Na2SO4, filtered, and the solvent was removed in vacuo. The crude product (S2) was isolated as a clear oil (1.73 g, 11.47 mmol, quant.). The spectral data of the compound were compared with the published ones.13

According to the analysis of related databases, 16179-97-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Podhajsky, Susanne M.; Iwai, Yasumasa; Cook-Sneathen, Amanda; Sigman, Matthew S.; Tetrahedron; vol. 67; 24; (2011); p. 4435 – 4441;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 113293-71-3, 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.113293-71-3, name is (6-Aminopyridin-3-yl)methanol, molecular formula is C6H8N2O, molecular weight is 124.14, as common compound, the synthetic route is as follows.

To a stirring of (6-aminopyridin-3-yl)methanol (1.24 mg, 10.0 mmol) and ethyl 2-chloro-3-hydroxyacrylate, potassium salt (29) (3.76 g, 20.0 mmol) in EtOH (10 mL) at room temperature was added conc sulfuric acid (10.0 mmol) dropwise. The reaction mixture was stirred at room temperature for 15 minutes and pyridine (0.92 g, 12.0 mmol) was added. The resulting mixture was heated at 85 C. overnight. The reaction was cooled to room temperature and the solvent was concentrated. The residue was taken in water and the solution was adjusted to pH 8 with saturated sodium bicarbonate. The crude product was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The crude product ethyl 6-(hydroxymethyl)imidazo[1,2-a]pyridine-3-carboxylate (59) was purified by silica chromatography. 1H NMR (400 MHz, d6-DMSO) delta 9.16 (d, J=6.8 Hz, 1H), 8.26 (s, 1H), 7.67 (s, 1H), 7.19 (dd, J=1.6, 6.8 Hz, 1H), 5.57 (t, J=6.4 Hz, 1H), 4.63 (d, J=6.0, 2H), 4.36 (q, J=7.2 Hz, 2H), 1.35 (t, J=6.8 Hz, 3H). MS m/z 221.1 (M+1)+.

Statistics shows that 113293-71-3 is playing an increasingly important role. we look forward to future research findings about (6-Aminopyridin-3-yl)methanol.

Reference:
Patent; MOLTENI, Valentina; PETRASSI, Hank Michael James; LI, Xiaolin; LIU, Xiaodong; LOREN, Jon; NABAKKA, Juliet; NGUYEN, Bao; YEH, Vince; US2013/59832; (2013); 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 23056-33-9, name is 2-Chloro-4-methyl-5-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 2-Chloro-4-methyl-5-nitropyridine

Zinc (15.97 g, 244.0 mmol) was suspended in acetic acid (240 ml) and cooled to 0C. Solid 2-(2-chloro-5-nitropyridin-4-yl)-N,N-dimethylethenamine (5.56 g, 24.42 mmol) was added portion- wise over about 5 minutes and then the reaction mixture was placed under an atmosphere of argon. The reaction was stirred for 18 h, after which time LCMS analysis indicated that the reaction was complete. The mixture was filtered through Celite, washing with EtOAc. The filtrate was concentrated to give a brown oil. The reaction mixture was partitioned between EtOAc and IN NaOH. The aqueous layer was extracted with EtOAc (3x) and the combined organic layer was dried over Na2S04, filtered and concentrated. The residue was adsorbed onto silica gel and purified by flash column chromatography on silica gel, eluting with EtOAc/isohexane (0-100%) to give 2.79 g of an off-white solid, that is approximately a 10: 1 mixture of the title compound along with 5-methoxy-lH-pyrrolo[2,3-c]pyridine as a minor impurity. The mixture was taken forward into the next step as is. LRMS (ESI) calc’d for (C7H5C1N2) [M+H]+, 153; found 153

With the rapid development of chemical substances, we look forward to future research findings about 23056-33-9.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALTMAN, Michael, D.; FISCHER, Christian; KATZ, Jason, D.; WILLIAMS, Theresa, M.; ZHANG, Xu-Fang; ZHOU, Hua; WO2013/181075; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 13466-38-1, 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. 13466-38-1, name is 5-Bromopyridin-2-ol. A new synthetic method of this compound is introduced below.

Example 142 To a solution of 5-bromopyridin-2-ol (1.0 g, 5.75 mmol) in DMF (10 mL) at RT, potassium tert-butoxide (0.68 g, 6.07 mmol) was added and the mixture was stirred for 30 min. To this mixture, (bromomethyl)cyclopropane (1.03 g, 8.62 mmol) was added, and the resulting mixture was stirred at 70 C. for 2 h. The mixture was allowed to cool to RT, diluted with EtOAc (50 mL) and quenched with water (20 mL). The organic layer was washed with water (2*20 mL) and brine (20 mL), dried over anhydrous MgSO4 and filtered. The filtrate was concentrated in vacuo to afford 5-bromo-1-(cyclopropylmethyl)pyridin-2(1H)-one. 1-(Cyclopropylmethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one was prepared in analogous fashion to Example 140, except 5-bromo-1-(cyclopropylmethyl)pyridin-2(1H)-one was used in place of 5-bromo-1-ethylpyridin-2(1H)-one. Compound 232 was prepared from compound 8 in analogous fashion to Example 140, except 1-(cyclopropylmethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one was used in place of 1-ethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one. ESI-MS m/z: 530.3 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13466-38-1, its application will become more common.

Reference:
Patent; INTELLKINE, LLC; INFINITY PHARMACEUTICALS, INC.; CASTRO, Alfredo C.; EVANS, Catherine A.; JANARDANANNAIR, Somarajannair; LESCARBEAU, Andre; LIU, Tao; SNYDER, Daniel A.; TREMBLAY, Martin R.; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; US2013/53362; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 95727-86-9, name is 5-(Trifluoromethyl)picolinonitrile, the common compound, a new synthetic route is introduced below. Application In Synthesis of 5-(Trifluoromethyl)picolinonitrile

Preparation Example 6 The same procedure as in Preparation Example 5 was repeated except that 20 g of 2-cyano-5-trifluoromethylpyridine was used in place of 2-cyano-3-chloro-5-trifluoromethylpyridine, to obtain 15 g of 5-trifluoromethylpyridine-2-carboxylic acid.

The synthetic route of 95727-86-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ishihara Sangyo Kaisha, Ltd.; US4367336; (1983); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 96424-68-9, 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. 96424-68-9, name is 2-Bromo-3-chloropyridine. A new synthetic method of this compound is introduced below.

A mixture of 2-bromo-3-chloropyridine (203.8 g, 1.06 moles), sodium tert-amylate (147 g, 1.27 moles), tert-butyl (3R)-3-aminopiperidine-1-carboxylate (249.5 g, 1.25 moles) in toluene (2 L) was heated to 80 C. To this solution was added chloro(di-2-norbornylphosphino)(2-dimethylaminoferrocen-1-yl) palladium (II) (6.1 g, 10.06 mmol) followed by heating to 105 C. and holding for 3 h. The reaction mixture was cooled to room temperature, 1 L of water was added, then the biphasic mixture was filtered through Celite. After layer separation, the organic phase was washed with 1 L of water followed by treatment with 60 g of Darco G-60 at 50 C. The mixture was filtered through Celite, and concentrated to a final total volume 450 mL, resulting in the precipitation of solids. To the slurry of solids was added 1 L of heptane. The solids were collected via filtration and then dried to afford the title compound as a dull orange solid (240.9 g, 73% yield).1H NMR (CDCl3) delta 8.03 (m, 1H), 7.45 (m, 1H), 6.54 (m, 1H), 5.08 (br s, 1H), 4.14 (br s, 1H), 3.85-3.30 (m, 4H), 2.00-1.90 (m, 1H), 1.80-1.55 (m, 4H), 1.43 (br s, 9H).UPLC (UPLC-MS Method 1): tR=0.72 min.MS (ES+) 312.0 (M+H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,96424-68-9, 2-Bromo-3-chloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Pfizer Inc.; Darout, Etzer; Dullea, Robert; Hawkins, Julie Jia Li; Londregan, Allyn T.; Loria, Paula M.; Maguire, Bruce; McClure, Kim F.; Petersen, Donna N.; Piotrowski, David W.; US2014/315928; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1000342-71-1, 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. 1000342-71-1, name is 6-Bromo-1H-pyrrolo[3,2-c]pyridine. A new synthetic method of this compound is introduced below.

General procedure: To a stirred solution of 5-bromo-1H-pyrrolo[2,3-c]pyridine (1.5 g, 7.61 mmol) in DMF (15 mL), KOH (1.27 g, 11.42 mmol) was added at RT. The resulting solution was stirred for 30 min. Then, fert-butyl 3- (bGammaomomethyl)piperidine-1-caoxylate (3.17 g, 22.84 mmol) was added at 0 C, and stirred at RT for 16h. The reaction mixture was diluted with water (70 mL) and extracted with EtOAc (2 x 70 mL), the combined organic layers were dried over anhydrous Na2SO4, and concentrated under reduced pressure. The crude compound was purified by flash column chromatography and eluted with 30% EtOAc/ pet ether to obtain the title compound (1.6 g, 54%) as an off white solid. LC-MS (method 1): Rt =2.47 min; m/z = 394.24 (M+H+)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1000342-71-1, 6-Bromo-1H-pyrrolo[3,2-c]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; ORYZON GENOMICS, S.A.; SALAS SOLANA, Jorge; CARCELLER GONZALEZ, Elena; ORTEGA MUNOZ, Alberto; (195 pag.)WO2018/149986; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 109-09-1, 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.109-09-1, name is 2-Chloropyridine, molecular formula is C5H4ClN, molecular weight is 113.54, as common compound, the synthetic route is as follows.

General procedure: 20 mL scintillation vial was charged with a solution of MnCl2THF1.6 (3 mol%, 3 mg, 0.012mmol) in 3 mL THF in a glove box. The corresponding electrophile (0.41 mmol, 1 equiv.) andinternal standard, mesitylene (0.41 mmol, 1equiv.), were added. After five minutes of stirring atroom temperature, the Grignard solution (1.2- 2.6 equiv.) was added dropwise and the reactionwas stirred at room temperature. The reaction mixture was removed from the glovebox andquenched with a saturated K2CO3 solution (3 mL) and EtOAc (3 mL). The organic layer wasextracted with EtOAc (3 x 3mL), and dried over MgSO4. The solution was then filtered andconcentrated. The crude product was purified via a silica plug.

The chemical industry reduces the impact on the environment during synthesis 109-09-1, I believe this compound will play a more active role in future production and life.

Reference:
Article; Petel, Brittney E.; Purak, Merjema; Matson, Ellen M.; Synlett; vol. 29; 13; (2018); p. 1700 – 1706;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem