Tag: M.W:100-200

Reference of 33252-28-7, 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. 33252-28-7, name is 6-Chloronicotinonitrile, molecular formula is C6H3ClN2, 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.

Example 29 6-Bromonicotinonitrile. 6-Chloronicotinonitrile (13.8 g, 100 mmol) was heated at 145 C. in phosphorus tribromide (150 mL) for 32 h. After cooling, the mixture was concentrated in vacuo. To the residue was added phosphorus tribromide (150 mL), and the mixture was heated at 145 C. for another 32 h. After cooling, the mixture was concentrated in vacuo, and an ice-water mixture (500 mL) was added. Sodium bicarbonate was added to neutralize the mixture, and the product was extracted with ethyl acetate (3*250 mL). The combined organic extracts were washed with brine and dried over magnesium sulfate. The solvent was removed in vacuo, and the residue was chromatographed (hexanes-ethyl acetate) to give 14.9 g (81 %) of 6-bromonicotinonitrile as a white solid: 1H NMR (400 MHz, CDCl3) delta 7.66 (d, J=11.0 Hz, 1H), 7.80 (dd, J=3.1, 11.0 Hz, 1H), 8.67 (d, J=3.1 Hz, 1H); MS (M+H)+ m/z=183.0, 185.0.

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 33252-28-7, 6-Chloronicotinonitrile.

Reference:
Patent; Xue, Chu-Biao; Metcalf, Brian W.; Han, Amy Qi; Robinson, Darius J.; Zheng, Changsheng; Wang, Anlai; Zhang, Yingxin; US2005/192302; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 52378-63-9, (3-Aminopyridin-2-yl)methanol, 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, 52378-63-9, blongs to pyridine-derivatives compound. HPLC of Formula: C6H8N2O

(i) A solution sodium nitrite (2.38 g) in water (10 ml) was added dropwise to a stirred mixture of 3-amino-2-hydroxymethylpyridine (4.8 g) in aqueous hydrochloric acid (48% 10 ml) and water (5 ml) at 0-5 C. This solution of the diazonium salt was added to a hot solution of cuprous chloride (2.5 g) in conc. hydrochloric acid and following cessation of nitrogen evolution the mixture was heated on the steam bath for 0.5 hours, diluted with water and saturated with hydrogen sulphide. Filtration, concentration to low bulk and extraction with chloroform yielded 3-chloro-2-hydroxymethylpyridine (3.7 g), m.p. 42-44 (from n-pentane).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,52378-63-9, its application will become more common.

Reference:
Patent; Smith Kline & French Laboratories Limited; US4025527; (1977); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 884495-38-9 ,Some common heterocyclic compound, 884495-38-9, molecular formula is C7H6ClNO, 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: To a solution of Intermediate 15B (0.50 g, 4.46 mmol) and 6bromo4methoxynicotinonitrile (0.95 g, 4.46 mmol) in dioxane (20 mL) was added K2CO3 (1.54 g, 11.15 mmol) and XANTPHOS (0.52 g, 0.89 mmol) and the resulting reaction mixture was degassed with nitrogen for 5 minutes. Pd2(dba)3(0.41 g, 0.45 mmol) was added and the resulting mixture was degassed again for 5 minutes then heated at 100 C for 16 h. The reaction mixture was cooled to ambient temperature, filtered through Celite and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (Redisep24 g, 2 2.5 % MeOH in DCM), to obtain Intermediate 15C (0.40 g, 36.70%) as a pale yellow solid.1H NMR (400 MHz, DMSOd6) G ppm 2.65 (t, J = 6.78 Hz, 2 H), 3.61 (td, J = 6.78, 5.02 Hz, 2 H), 4.10 (s, 3 H), 4.62 4.76 (m, 1 H), 7.58 (s, 1 H), 7.81 (s, 1 H), 8.47 (s, 1 H), 8.73 (s, 1 H). LCMS (MethodI): retention time 0.83 min, [M+H] 245.3

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,884495-38-9, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YADAV, Navnath Dnyanoba; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; GUNAGA, Prashantha; PANDA, Manoranjan; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (444 pag.)WO2018/222795; (2018); A1;,
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Pyridine | C5H5N – PubChem

Synthetic Route of 1370347-50-4, 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 1370347-50-4, name is (S)-1-(3,5-Dichloropyridin-4-yl)ethanol. This compound has unique chemical properties. The synthetic route is as follows.

Dissolve (S)-1-(3,5-dichloropyridin-4-yl)ethanol (5.02 g, 26.14 mmol) in dichloromethane (DCM, 100 mL) and cool the flask in an ice bath. Add triethylamine (TEA, 3.5 mL, 25.11 mmol) followed by the dropwise addition of methanesulfonyl chloride (2.2 mL, 28.42 mmol). Remove the ice bath and allow the reaction to warm to RT. After 4 hours, quench the reaction with water (100 mL) and separate layers. Extract the aqueous layer with DCM (50 mL) followed by 20% isopropyl alcohol (IPA)/chloroform (50 mL). Combine the organic extracts, dry over anhydrous sodium sulfate, filter and concentrate in vacuo. Yield: 7.15 g, (100%). MS (ES) m/z 270 [M+1]+.

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 1370347-50-4, (S)-1-(3,5-Dichloropyridin-4-yl)ethanol.

Reference:
Patent; ELI LILLY AND COMPANY; US2012/83511; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 57963-08-3, 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 57963-08-3, name is 5,6-Dimethylpyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

DIPEA (0.257 g, 1.99 mmol) was added to a suspension of intermediate Z48 (0.20 g, 0.66 mmol), 5,6-dimethylpyridin-2-amine (0.097 g, 0.80 mmol) and HATU (0.38 g, 1.00 mmol) in DCM (15 mL) at 0 C. The reaction was allowed to warm to rt and was stirred for 18 h before being quenched with water, extracted with DCM (2 x 40 mL), washed with brine and dried over anhydrous Na2S04. Solvents were removed in vacuo and the crude product was purified by flash column chromatography (10% ethyl acetate in hexane) to afford intermediate Y21 (0.091 g, 0.22 mmol, 34%) as a white solid. 1H NMR (DMSO-d6, 400 MHz) delta: 10.86 (1H, s), 7.95-7.93 (1H, d, J= 8.4 Hz), 7.89-7.88 (1H, d, J= 2.0 Hz), 7.81-7.79 (1H, dd, J= 8.4 Hz, 2.0 Hz), 7.56-7.54 (1H, d, J= 8.4 Hz), 7.47-7.45 (1H, d, J= 8.0 Hz), 2.35 (3H, s), 2.22 (3H, s), 1.36 (9H, s).

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 57963-08-3, 5,6-Dimethylpyridin-2-amine.

Reference:
Patent; H. LUNDBECK A/S; MALTAS, Philip James; WATSON, Stephen; LANGGARD, Morten; DAVID, Laurent; WO2014/114779; (2014); 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 88912-24-7, name is 5,6-Dichloropicolinic acid. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

To a 100 mE round bottom flask equipped with a magnetic stirrer, reflux condenser and a nitrogen inlet were added 5,6-dichioropicolinic acid (5.00 g, 23.1 mmol), TEA (8.2 g, 81.0 mmol), ACN (39.5 g) and water (15.1 g). The solution was sparged for 30 mm with nitrogen (1 mE/mm) Afier sparging, triphenylphosphine (TPP; 0.18 g, 0.686 mmol) and palladium(II) acetate (0.078 g, 0.347 mmol) were added to the solution. Furan-2-boronic acid (3.3 g, 28.9 mmol) was added in one portion, and heating was initiated. The reaction mixture was heated to 55 C., and was sampled and analyzed by liquid chromatography. No boronic acid was remaining after two hours, and heating was stopped. The reaction mixture was allowed to cool overnight and then was heated to 45 C. Once at temperature, 50% sulfuric acid (7.1 g) was added. No precipitation was observed, so the mixture was cooled. After 30 mm at <5 C., no solids were observed and water (25.7 g) was added. A precipitate formed which was allowed to cool for 1 h and isolated by filtration. The flask was rinsed with cold mother liquor to isolate all of the product. The wetcake was then rinsed with cold ACN- water solution (8.75 g and 11.25 g, respectively). The palladium content was analyzed in the wetcake, wash and mother liquors, with 81% of the palladium in the mother liquor and wash, and 19% in the wet cake. 99% of the total palladium added was recovered. With the rapid development of chemical substances, we look forward to future research findings about 88912-24-7. Reference:
Patent; Dow AgroSciences LLC; Biswas, Sanjib; Chakrabarti, Reetam; Huffman, Lauren M.; Leng, Ronald B.; Schuitman, Abraham D.; Spiers, Karin; Stottlemyer, Alan L.; Epp, Jeffrey B.; (18 pag.)US2016/340311; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 722550-01-8, 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 722550-01-8 as follows.

General procedure: 2-(5-Bromo-2-isopropoxy-4~methoxyphenyl)-7-(pyrrolidin”l-yl)imidazo| l,2-o]~ pyridine hydrobromide 73 was prepared in the same manner as 2-(5-bromo-2,4-dimethoxy- phenyl)”7-(pyrro3idin~l~yl)imidazo[l,2-a]pyridine 9a and was obtained as an off-white solid (26% yield). 1H NMR. (400 MHz, DMSO-c 6): delta 13.04 (s, IH), 8.61 (d, J= 7.6 Hz, IH), 8.11 (s, IH), 8.02 (s, IH), 6.95 (s, H), 6.93 (s, IH), 6.27 (s, IH), 5.06-4.97 (m, IH), 3,94 (s, 3H), 3,48-3.40 (m, 4H), 2.06-1.99 (rn, 4H), 1.44 (s, 3H), 1.42 (s, 31 1 }: HPLC (Method 3) >99% (AUC), fR = 18.93 min; ESI MS m/z 4?()| M + H]+ . A solution of 2-bromo-1-(5-bromo-2,4-dimethoxyphenyl)ethanone 7 (124 rng, 0.367 mmol) and 4-(pyrrolidin-1-yl)pyridin-2-amine 8 (60 mg, 0.367 mmol) in acetone (4 mL) was heated at 75 C for 16 h. The reaction mixture was cooled to room temperature; the white precipitate was collected by filtration and solid was washed with acetone. The solid was suspended in aqueous ammonia solution (10 ml.) and stirred for 2 h. The free base was collected by filtration and solid was washed with water, dried under reduced pressure to yield 2-(5-bromo-2,4-dimethoxyphenyl)-7-(pyrrolidin-1-yl)imidazo[1,2-a]pyridine 9a (51 mg, 35%) as an off-white solid. 1H NMR (300 MHz, CDCl3): delta 8.55 (s, 1H), 7.83 (d, J = 7.4 Hz, 1H), 7,80 (s, 1H), 6.55 (s, 1H), 6,43 (d, J = 2.2 Hz, 1H), 6.33 (dd, J = 2,2, 7,4 Hz, 1H), 3 ,99 (s, 3H), 3 ,94 (s, 3H), 3.40-3,30 (m, 4H), 2.10-2.00 (m, 4H); HPLC (Method 2) >99% (AUC), tR= 19.12 min: APCI MS m/z 404 [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,722550-01-8, its application will become more common.

Reference:
Patent; ONCOTHERAPY SCIENCE, INC.; MATSUO, Yo; HISADA, Shoji; NAKAMURA, Yusuke; CHAKRABARTI, Anjan; RAWAT, Manish; RAI, Sanjay; SATYANARAYANA, Arvapalli, Venkata; DUAN, Zhiyong; TALUKDAR, Arindam; RAVULA, Srinivas; DECORNEZ, Helene; (491 pag.)WO2017/58503; (2017); 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. 54-92-2, name is N’-Isopropylisonicotinohydrazide. A new synthetic method of this compound is introduced below., Safety of N’-Isopropylisonicotinohydrazide

To solution containing (E)-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)acrylic acid (200.0 mg, 0.70 mmol), N?-isopropylisonicotino hydrazide (188.2 mg, 1.05 mmol) and HATU (399.2 mg, 1.05 mmol) dissolved in DMF (5.0 ml), N,N-diisopropylethylamine (DIPEA)(0.18 ml, 1.05 mmol) was slowly drop-wise added and stirred at room temperature for 12 hr. The reaction mixture was diluted with EtOAc, washed with water and brine, dried with anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was separated through silica gel chromatography (n-hexane:EtOAc=3:1) for refinement and dried so that ivory (E)-tert-butyl 3-(3-(2-isonicotinoyl-1-isopropylhydrazinyl)-3-oxoprop-1-enyl)-1H-indole-1-carboxylate was obtained (108 mg, 34.4%). [0353] 1H-NMR (MeOD, 500 MHz): delta 8.87 (2H, d, J=4.6 Hz, aromatic), 8.18 (1H, d, J=8.3 Hz, aromatic), 7.95 (3H, m, aromatic), 7.84 (1H, d, J=15.7 Hz, indole-CH?CH-), 7.58 (1H, m, aromatic), 7.34 (1H, t, J=7.6 Hz, aromatic), 7.13 (1H, m, aromatic), 6.96 (1H, d, J=15.2 Hz, indole-CH?CH-), 5.03 (1H, m, -N-CH-(CH3)2), 1.71 (9H, s, Boc), 1.33 (6H, m, -N-CH-(CH3)2)

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, 54-92-2, N’-Isopropylisonicotinohydrazide.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY; LEE, Hyun Sun; KIM, Mun-Ock; CHOI, Yongseok; Lee, Kyeong; PARK, Jeong-Jun; SEO, Jee-Hee; JUNG, Hwayoung; CHO, Sungchan; US2014/57909; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 51454-63-8, 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. 51454-63-8, name is 2-(Hydroxymethyl)isonicotinonitrile, molecular formula is C7H6N2O, 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.

The product of the previous step (1.4 g, 10.2 mmol) and N,N’-dicyclohexylcarbodiimide (6.2 g, 30.0 mmol) were added to a mixture of DMSO (22 ml) & anhydrous H3PO4 (0.45 g) and the reaction was left to stir 1.5 hours. The reaction was filtered and washed with diethyl ether (2 x 30 ml) and water (2 x 30 ml). The reaction layers was separated and the organic layer was washed with saturated brine (2 x 30 ml), dried with MgS04, filtered and evaporated in vacuo to yield (iid) as a yellow solid which was taken towards the next step without purification.

According to the analysis of related databases, 51454-63-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KUDOS PHARMACEUTICALS LIMITED; WO2006/21801; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1256808-59-9, 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.1256808-59-9, name is 5-Fluoro-3-methylpicolinic acid, molecular formula is C7H6FNO2, molecular weight is 155.13, as common compound, the synthetic route is as follows.

To a solution of tert-butyl ((3aR,4R,8S)-4-(6-amino-3-fluoropyridin-2-yl)-4,7,7- trimethyl-8-oxido-3,3a,4,7-tetrahydro-2H-isothiazolo[l,5-a][l,4]thiazin-6-yl)carbamate (Int- 39BA, 150 mg, 0.35 mmol) in THF (20 mL) was added 5-fluoro-3-methylpicolinic acid (82 mg, 0.53 mmol) followed by T3P (1.1 g, 1.75 mmol, 50% in ethyl acetate), and diisopropylethylamine (267 mg, 2.1 mmol). The reaction was stirred at 70 C for 4 h. After that, the reaction mixture was diluted with aqueous saturated sodium hydrogencarbonate solution (20 mL) and extracted with ethyl acetate (3 x 30 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated to give a crude product. The crude was purified by column chromatography (silica gel, eluting with petroleum ether / ethyl acetate 1: 1) to yield, after drying in vacuo, the title compound as a yellow solid (130 mg, 66% yield). XH NMR (CDC13, 400 MHz): delta 0.81-0.91 (m, 3 H), 1.49-1.59 (m, 9 H), 1.67- 1.76 (m, 6 H), 2.08-2.22 (m, 1 H), 2.52-2.64 (m, 1 H), 2.76-2.87 (m, 3 H), 3.71-3.87 (m, 2 H), 5.21 (dd, / = 7.1, 11.0 Hz, 1 H), 7.37 (dd, / = 2.3, 8.8 Hz, 1 H), 7.48-7.57 (m, 1 H), 8.37 (d, / = 2.5 Hz, 1 H), 8.44 (dd, / = 3.0, 8.9 Hz, 1 H), 10.46 (s, 1 H), 11.00 (br s, 1 H). MS (ES+) mJz 563.2 [M+H] .

Statistics shows that 1256808-59-9 is playing an increasingly important role. we look forward to future research findings about 5-Fluoro-3-methylpicolinic acid.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; CUENI, Philipp; DOLENTE, Cosimo; GUBA, Wolfgang; HAAP, Wolfgang; KUGLSTATTER, Andreas; OBST SANDER, Ulrike; PETERS, Jens-Uwe; ROGERS-EVANS, Mark; VIFIAN, Walter; WOLTERING, Thomas; (231 pag.)WO2016/55496; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem