Day: March 4, 2022

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.89026-78-8, name is 6-Chloro-N-methylpyridin-2-amine, molecular formula is C6H7ClN2, molecular weight is 142.59, as common compound, the synthetic route is as follows.COA of Formula: C6H7ClN2

To a stirred solution of 6-chloro-N-methylpyridin-2-amine (0.3 g, 2.10 mmol) in toluene:EtOH:water (1:1:1; 3 ml) was added Cs2CO3 (1.37 g, 4.21 mmol) and phenylboronic acid (0.385 g, 3.16 mmol) at rt. The reaction mixture was degassed for 30 mm before adding Pd(PPh3)4 (0.121 g, 0.105 mmol) at a The reaction mixture was heated at 120C for 16 h. The resulting mixture was cooled to rt, diluted with water (20 ml) and extracted with EtOAc (3 x 25 ml). The combined organic phase was washed with water (20 ml). The organic phase was separated, dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting crude material was purified by flash chromatography (3-7% EtOAc in hexane) yielding N-methyl-6-phenylpyridin-2-amine (0.308 g, 1.67 mmol). LCMS:Method C, 1.48 mi MS: ES+ 185.14; ?H NMR (400 MHz, CDC13) (5ppm 7.97 – 8.02 (m, 2 H), 7.55 (t, J=8.0 Hz, 1 H), 7.44 – 7.52 (m, 2 H), 7.37 – 7.41 (m, 1 H), 7.06 (d, J=7.6 Hz, 1 H), 6.39 (d, J8.4 Hz, 1 H), 3.00 (s, 3 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89026-78-8, 6-Chloro-N-methylpyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; GIBSON, Karl Richard; JONES, Alison; KEMP, Mark Ian; MADIN, Andrew; STOCKLEY, Martin Lee; WHITLOCK, Gavin Alistair; WOODROW, Michael D.; (109 pag.)WO2017/141036; (2017); 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. 13466-35-8, name is 3-Chloro-2-hydroxypyridine, the common compound, a new synthetic route is introduced below. HPLC of Formula: C5H4ClNO

EXAMPLE 1 3-Chloro-5-octyl-2-(4-octyloxyphenyl)pyridine 10.5 ml (203.0 mmol) of bromine are added dropwise at 0° C. to 23.9 g (184.5 mmol) of 3-chloro-2-hydroxypyridine in 240 ml of dimethylformamide, and the mixture is stirred at room temperature for 2 hours. 200 ml of water are subsequently added, and 30 g of sodium sulfite in 100 ml of water are added dropwise. After 15 minutes, the mixture is extracted three times with 200 ml of dichloromethane in each case, the combined organic phases are dried over sodium sulfate and filtered, and the filtrate is evaporated to dryness, giving 36.58 g of 5-bromo-3-chloro-2-hydroxypyridine. STR13 m.p.: 168° C. (decomp.)

The synthetic route of 13466-35-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoechst Aktiengesellschaft; US5629428; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 58539-65-4, 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 58539-65-4 as follows.

A mixture of X-2 (13 g, 95.6 mmol, 1 eq) and 18.2 mL of N,Ndimethylformamide dimethyl acetal was heated at 50C for 2 hrs. During the second hour, all the volatiles was removed. The residue was cooled to rt., diluted with 100 mL of anhydrous N,Ndimethylformamide, and then treated carefully with batch wise portions of sodium hydride (5 g, 124.3 mmol, 1.3 eq, 60% oil dispersion; caution: vigorous evolution of hydrogen). The mixture was heated at 80C for 2.5 hrs, and then ice-cooled, treated cautiously with 25 mL of 2-propanol, and then maintained at 0-5C overnight. The solid were collected, and then dissolved in 10 mL of hot water. The solution was filtered, the filtrate was ice-cooled and then treated dropwise with concentrated hydrochloric acid to pH=-7.0. After storage at 0-5C for 3 hrs, the precipitated solids were collected, washed with ice-cold water, and dried in vacuum to give X-3 (3 g, 32% yield). ?H NMR (DMSO-d6, 300 MHz): oe 8.90 (s, 1H), 8.49 (d, J=7.6 Hz, 1H), 7.51-7.43 (m, 2H), 6.61 (d, J =7.6 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,58539-65-4, its application will become more common.

Reference:
Patent; INTERMUNE, INC.; RAMPHAL, Johnnie, Y.; BUCKMAN, Brad, Owen; EMAYAN, Kumaraswamy; NICHOLAS, John, Beamond; SEIWERT, Scott, D.; WO2015/153683; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 55404-31-4, 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. 55404-31-4, name is 3-Bromo-2-chloro-4-methylpyridine. A new synthetic method of this compound is introduced below.

Example 193; Synthesis of 3-bromo-4-methylpyridin-2(1H)-one; To a resealable pressure vessel charged with 3-bromo-2-chloro-4-picoline (1.200 g, 5.81 mmol) was added formic acid (13.1 ml, 348 mmol) and water (4.00 ml, 222 mmol). The tube was sealed and the solution heated to 1200C. After 72 hrs, the solution was cooled to RT and concentrated in vacuo. The residue was purified by reverse phase chromatography (neutral) to afford 3-bromo-4- methylpyridin-2(1H)-one as a white solid. M+H+ = 188.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,55404-31-4, 3-Bromo-2-chloro-4-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; WO2008/11109; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 957187-27-8, 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 957187-27-8, name is 8-Bromo-6-chloroimidazo[1,2-a]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

Step B: 2′-Amino-r,2,2-trimethyl-6-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)spiro[chroman-4,4′- imidazol]-5′(l’H)-one (50 mg, 0.13 mmol; see Example 103, Step A) and 8-bromo-6-chloroimidazo[l,2- ajpyridine (60 mg, 0.26 mmol) were diluted with dioxane (1 mL), followed by the addition of Pd(PPh3)4 (7.5 mg, 0.0065 mmol) and Na2C03 (324 mu, 0.65 mmol). The reaction was sealed, heated to 85C and stirred for 12 hours. The reaction was loaded directly onto silica gel and eluted with 1-10% methanol/DCM (1% Nu¾OmicronEta) to afford 2′-amino-6-(6-chloroimidazo[l,2-a]pyridin-8-yl)-l’,2,2- trimethylspiro[chroman-4,4′-imidazol]-5′(rH)-one (18 mg, 0.044 mmol, 34% yield), m/z (APCI-pos) M+l = 410.2

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 957187-27-8, 8-Bromo-6-chloroimidazo[1,2-a]pyridine.

Reference:
Patent; ARRAY BIOPHARMA INC.; HUNT, Kevin, W.; RIZZI, James, P.; COOK, Adam; WO2011/72064; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 98121-41-6, Adding some certain compound to certain chemical reactions, such as: 98121-41-6, name is 3-Amino-5,6-dichloropyridine,molecular formula is C5H4Cl2N2, 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 98121-41-6.

Precursor alpha: 2,3-Dichloro-5-isopropylthiopyridine 13.1 g (0.08 mol) of 3-amino-5,6-dichloropyridine in 120 ml of methylene chloride were reacted with 25 g (0.16 mol) of diisopropyl disulfide and 12.4 g (0.12 mol) of tert-butyl nitrite in 70 ml of methylene chloride by a method similar to Example 1, Precursor alpha. This gave 30 g of the dark oil (approximately 40% of product of value) which was further reacted without further purification. 1H-NMR (in d6 dimethyl sulfoxide): delta [ppm]=1.25 (d, 2*CH3); 3.7 (m, CH); 8.2 and 8.3 (2*d, pyr H).

According to the analysis of related databases, 98121-41-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BASF Aktiengesellschaft; US6448205; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.72141-44-7, name is 4-Chloro-2-methoxypyridine, molecular formula is C6H6ClNO, molecular weight is 143.5709, as common compound, the synthetic route is as follows.SDS of cas: 72141-44-7

(a); 5.76 g (40.1 mmol) of 4-chloro-2-methoxypyridine was dissolved in 20 ml of dimethylformamide, and a dimethylformamide (20 ml) solution of 8.01 g of N-bromosuccinimide (98%, 44.1 mmol) was dropwise added over a period of 30 minutes. After stirring at room temperature for 2 days, an unreacted material was confirmed, and thus 2.85 g of N-bromosuccinimide (98%, 16 mmol) was further added, followed by stirring at room temperature further for 3 days. The reaction mixture was poured into 250 ml of water, followed by extraction with ethyl ether (100 ml each) three times. The organic layer was washed with water (100 ml), a sodium thiosulfate aqueous solution (100 ml) and then a saturated sodium chloride solution (100 ml), dried over magnesium sulfate and subjected to filtration, and the solvent was distilled off under reduced pressure. The obtained crude product was purified by silica gel chromatography to obtain 7.10 g (yield: 80%) of 5-bromo-4-chloro-2-methoxypyridine. 1H-NMR(CDCl3, 400MHz): delta (ppm) =3.91 (s, 3H), 6. 89 (s,1H), 8.28(s,1H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,72141-44-7, 4-Chloro-2-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1679003; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 33252-28-7, 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. 33252-28-7, name is 6-Chloronicotinonitrile. A new synthetic method of this compound is introduced below.

Triethylamine (5.51 g, 4 mL, 54.6 mmol, 2.7 eq) is added to a solution of 6-chloro- nicotinonitrile (2.76 g, 20 mmol, 1 eq), (i?)-2-methyl- piperazine (2.0Og, 20 mmol, 1 eq) in DMF (15 mL), and the resulting solution is stirred at rt for 36 h. A white precipitate of triethylamine hydrochloride forms in the course of the reaction. Water (15 mL) and EtOAc (100 mL) are added, the organic layer is separated, dried over sodium sulfate and concentrated under reduced pressure to a white residue. The solid is further dried under high vacuum to yield the desired product as a white solid (2.3 g, 59%). IH NMR (400 MHz, CHLOROFORM-*/) delta ppm 8.32 (d, J=2.40 Hz, 1 H), 7.52 (dd, J=9.09, 2.27 Hz, 1 H), 6.52 (d, J=8.97 Hz, 1 H), 4.14 – 4.24 (m, 2 H), 3.01 – 3.07 (m, 1 H), 2.72 – 2.94 (m, 3 H), 2.52 (dd, J=12.76, 10.36 Hz, 1 H), 1.07 (d, J=6.32 Hz, 3 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,33252-28-7, 6-Chloronicotinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; WO2008/110611; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 52311-50-9 ,Some common heterocyclic compound, 52311-50-9, molecular formula is C7H8ClNO, 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.

To a degassed mixture of 4-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2- yl)benzamide ( 9.4g, 38 mmol) and 2-chloro-4-ethoxypyridine ( 5g, 31.7 mmol) in dioxane was added Brettphos-prePd (catalytic amount) and CS2CO3 (12.3 g, 37.8 mmol) under N2atmosphere. The mixture was heated to 100 C and stirred for 3.5 hours. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated, and the residue was purified on silic-gel (PE: EA = 100% ~ 30%) to give N-(4-ethoxypyridin-2-yl)-4-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl)benzamide (8.8 g, yield 75%). 1HNMR (400MHz, CDC13): 5=8.74 (s, 1 H), 8.05~8.02(m, 1 H), 8.01 (s, 1 H), 7.94-7.89 (m, 4 H), 6.60-6.59 (m, 1 H), 4.20-4.14 (m, 2 H), 1.47-1.43 (m, 3 H), 1.36 (s,12 H), MS (ESI):M/Z (M+l)=369.19.

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. 52311-50-9, 2-Chloro-4-ethoxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WU, Hao; KIM, Ronald M.; LIU, Jian; GAO, Xiaolei; BOGA, Sobhana Babu; GUIADEEN, Deodialsingh; KOZLOWSKI, Joseph; YU, Wensheng; ANAND, Rajan; YU, Younong; SELYUTIN, Oleg B.; GAO, Ying-Duo; LIU, Shilan; YANG, Chundao; WANG, Hongjian; WO2014/114185; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 57963-08-3, name is 5,6-Dimethylpyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. name: 5,6-Dimethylpyridin-2-amine

(A) 5,6-dimethylimidazo[1,2-a]pyridine (0313) A mixture of 5,6-dimethylpyridin-2-amine (2.0 g, 16 mmol), 40% chloroacetaldehyde aqueous solution (3.2 mL, 20 mmol) and ethanol (40 mL) was heated under reflux overnight. The solvent was evaporated under reduced pressure, and the reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the residue was purified by NH silica gel column chromatography (hexane/ethyl acetate) to give the title compound (2.5 g). 1H NMR (300 MHz, CDCl3) delta2.35 (3H, s), 2.53 (3H, s), 7.05 (1H, d, J = 9.4 Hz), 7.46 (2H, t, J = 4.5 Hz), 7.65 (1H, d, J = 1.1 Hz).

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

Reference:
Patent; Takeda Pharmaceutical Company Limited; KIMURA, Eiji; MIYANOHANA, Yuhei; OGINO, Masaki; TANAKA, Yuta; FUSHIMI, Makoto; OKAWA, Tomohiro; HANYA, Yuki; KOIKE, Tatsuki; (67 pag.)EP3239150; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem