Tag: M.W:200-300

Synthetic Route of 84539-34-4, 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 84539-34-4 as follows.

A solution of 3,5-dibromo-4-amino-pyridine 1 (4.0 g, 15.87 mmol), Pd(PPh3)4 (0.91 g, 0.78 mmol) and aqueous solution of Na2CO3 (23.8 ml, 2M ) in toluene (80 ml ) is added to a solution of dichlorobenzene boronic acid (6.23 g, 46.4 mmole) in ethanol (24 ml). The mixture is refluxed for 14 h., diluted with ethyl acetate and washed with saturated NH4Cl solution. The organic layer is dried over sodium sulfate and concentrated in vacuo. The residue is chromatographed on silica gel to give 2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,84539-34-4, its application will become more common.

Reference:
Patent; Bristol-Myers Squibb Company; US6352990; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 195044-14-5, 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 195044-14-5, name is 2-Bromo-6-tert-butylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

Example 58A[0972] 2-(benzylthio)-6-tert-butylpyridine[0973] To a solution of benzyl mercaptan (0.22 mL, 1.87 mmol) in anhydrous N,N- dimethylformamide (10 mL) was added a 1.0 M solution of potassium tert-butoxide in tetrahydrofuran (1.87 mL, 1.87 mmol) dropwise over 2 minutes. To the resulting suspension was added 2-bromo-6-tert-butylpyridine (0.20 g, 0.93 mmol), and the resulting mixture was stirred at 50 C for 16 hours. The cooled mixture was poured into water (50 mL) and extracted with ethyl acetate (50 mL), and the ethyl acetate layer was dried over Na2S04, filtered and concentrated in vacuo to give a crude product. Purification by column chromatography on silica gel using hexanes gave the titled compound. XH NMR (300 MHz, CDC13) delta ppm 1.35 (s, 9 H), 4.50 (s, 2 H), 6.93 – 7.03 (m, 2 H), 7.17 – 7.45 (m, 6 H); MS (APCI) m/z 258.3 (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 195044-14-5, 2-Bromo-6-tert-butylpyridine.

Reference:
Patent; ABBVIE INC.; LI, Tao; PATEL, Sachin, V.; PERNER, Richard, J.; RANDOLPH, John, T.; SCHRIMPF, Michael, R.; WOLLER, Kevin, R.; XIA, Zhiren; ZHANG, Qingwei; WO2013/49174; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1030626-87-9 , The common heterocyclic compound, 1030626-87-9, name is 8-Bromo-5-chloro-[1,2,4]triazolo[1,5-a]pyridine, molecular formula is C6H3BrClN3, 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.

A.5 (5-Chloro-[l, 2, 4]triazolo[l, 5-a]pyridin-8-yl)-(4-morpholin-4-yl-phenyl)-amine[0332] A suspension of 8-bromo-5-chloro-[l,2,4]triazolo[l,5-a]pyridine (160 mg, 0.69 mmol),4-morpholin-4-yl-phenylamine (135 mg, 0.76 mmol), sodium-tert-butoxide (93 mg, 0.96 mmol), tris(dibenzylideneacetone)dipalladium (0) (13 mg, 13.76 mumol) and Xantphos (16 mg, 27.52 mumol) in dry toluene is heated at 90 0C in a sealed tube under a nitrogen atmosphere for 16 hours. The reaction mixture is evaporated to dryness and the residue partitioned between dichloromethane and 10 % aqueous citric acid. The organic phase is further washed with water (Ix) and brine (Ix), dried over magnesium sulfate, filtered and evaporated. The solid residue (207 mg) is purified by flash chromatography (silica gel, dichloromethane/methanol 97:3) affording the title compound (70 mg) as a solid.

The synthetic route of 1030626-87-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALAPAGOS N.V.; BURRITT, Andrew; WO2008/65198; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1214328-96-7, 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 1214328-96-7, name is Methyl 3-bromo-6-chloropicolinate. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 2 Synthesis of 3-bromo-4,6-dichloro-pyridine-2-carboxylic acid methyl ester.2.1 Preparation of 3-bromo-6-chloro-pyridine-2-carboxylic acid N-oxideUrea hydrogen peroxide (65.32 g, 347.2 mmol) was added portionwise to a solution of trifluoroacetic anhydride (145.8 g, 694.4 mmol, 96.5 mL) in dichloromethane (577 mL) at 0 C. 3-Bromo-6-chloro-pyridine-2-carboxylic acid methyl ester (27.18 g, 108.5 mmol) was added to the mixture portionwise and the reaction was stirred at room temperature for 19 h. The reaction was quenched by the addition of water, and the organic layer was washed with water and saturated aqueous K2C03. The organic layer was dried (MgS04) and concentrated in vacuo to give 3-bromo-6-chloro-pyridine-2-carboxylic acid N-oxide as a yellow oil.Characterising data for the compound are as follows: NMR (400 MHz, CD3OD) delta ppm 7.77-7.75 (m, 2H) and 4.01 (s, 3H).

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 1214328-96-7, Methyl 3-bromo-6-chloropicolinate.

Reference:
Patent; SYNGENTA LIMITED; WHITTINGHAM, William Guy; HACHISU, Shuji; ASPINALL, Mary, Bernadette; HOTSON, Matthew, Brian; WO2011/144891; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 156094-63-2, 2-(Bromomethyl)-6-methoxypyridine, 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, Safety of 2-(Bromomethyl)-6-methoxypyridine, blongs to pyridine-derivatives compound. Safety of 2-(Bromomethyl)-6-methoxypyridine

A room temperature solution of 4-(6-(piperazin- 1 -yl)pyridin-3 -yl)-6-( 1 H-pyrazol-4- yl)pyrazolo[1,5-a]pyridine-3-carbonitrile bis(2,2,2-trifluoroacetate) (Example 698, Step 1; 6 mg, 0.0162 mmol) in dry DMA (900 tL) was treated sequentially with TEA (22.6 tL, 0.162 mmol) and 2-(bromomethyl)-6-methoxypyridine (9.82 mg, 0.0486 mmol). The reaction mixture was stirred overnight at room temperature before introducing additional TEA (1 tL, 0.01 mmol) and 2-(bromomethyl)-6-methoxypyridine (2mg, 0.01 mmol). The reaction mixture was stirred at room temperature until LCMS indicated the reaction was complete. The reaction mixture was directly purified by Cl 8 reverse-phase chromatography (15-80% ACN/water with 0.1% formic acid as the gradient eluent) to cleanly afford the title compound (2.5 mg, 51% yield). MS (apci) m/z = 492.2(M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,156094-63-2, 2-(Bromomethyl)-6-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; ARRAY BIOPHARMA, INC.; ANDREWS, Steven W.; BLAKE, James F.; CHICARELLI, Mark J.; GOLOS, Adam; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; (594 pag.)WO2017/11776; (2017); 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. 22282-70-8, name is 2-Fluoro-4-iodopyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2-Fluoro-4-iodopyridine

A solution of 2-fluoro-4-iodopyridine (10.00 g, 43.50 mmol) and ammonia (10 mL) in DMSO (20 mL) was stirred at 100 C for 40 h.Water (100 mL) was added to the reaction solution, and a solid was precipitated. The brown solid compound 10a (8.62 g, 90%) was obtained by filtration

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, 22282-70-8, 2-Fluoro-4-iodopyridine.

Reference:
Patent; JACOBIO PHARMACEUTICALS CO., LTD; MA, CUNBO; GAO, PANLIANG; CHU, JIE; WU, XINPING; WEN, CHUNWEI; KANG, DI; BAI, JINLONG; PEI, XIAOYAN; (171 pag.)TW2019/25186; (2019); A;,
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.849068-61-7, name is 5-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid, molecular formula is C8H5BrN2O2, molecular weight is 241.04, as common compound, the synthetic route is as follows.Application In Synthesis of 5-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid

To a solution of 5-bromo-lH-pyrrolo [2,3-b] pyridine-3-carboxylic acid (600 mg, 2.49 mmol)Of N, N-dimethylformamide (20 mL)To the solution was added 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (1.44 g, 7.43 mmol)1-hydroxybenzotriazole (1.01 g, 7.46 mmol) and2-isopropylamine (1.27 mL, 14.90 mmol),Stir overnight at room temperature.Saturated brine (20 mL) was added,Dichloromethane (15 mL x 3)Dried over anhydrous sodium sulfate, the solvent was removed,The concentrate was subjected to column chromatography (eluent: petroleum ether / ethyl acetate (v / v) = 5/1) to give the product as360 mg of a brown solid, yield: 51.3%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,849068-61-7, 5-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Liu Bing; Huang Jiuzhong; Zheng Changchun; Zhang Yingjun; Ouyang Luo; Mao Hongfen; Nie Biao; Xu Juan; Chen Hongfen; (137 pag.)CN106336413; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 97966-00-2 ,Some common heterocyclic compound, 97966-00-2, molecular formula is C5H2BrCl2N, 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 5-bromo-2,3-dichloropyridine (29) (11.7 g, 51.6 mmol) was added HBr (5M in AcOH) (51.6 ml, 258 mmol) at room temperature. Then the reaction mixture was heated to 70 C. After being stirred for 7 hrs at 70 C., the reaction mixture was diluted with ethyl acetate, quenched with H2O and extracted with ethyl acetate. The resulting organic layer was washed with 1M NaOH, dried over over Na2SO4 and concentrated in vacuo. The residue was recrystallized from hexane-ethyl acetate to afford 11.2 g of the desired product (41) in 80% yield as a white solid. 1H-NMR (DMSO-d6) delta: 8.55 (1H, s), 8.49 (1H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,97966-00-2, its application will become more common.

Reference:
Patent; SHIONOGI & CO., LTD.; Kurose, Noriyuki; Iso, Yasuyoshi; Yamaguchi, Naoko; Shao, Bin; Tafesse, Laykea; Zhou, Xiaoming; Yu, Jianming; US9156830; (2015); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 137520-99-1 ,Some common heterocyclic compound, 137520-99-1, molecular formula is C9H9Cl2NO2, 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 mixture of 2,6-dichloro-3-methylisonicotinic acid ethyl ester (10.0 g, 42.7 mmol), Example 7E and acetic acid (2.69 g, 44.9 mmol) in carbon tetrachloride (147 ml.) are added lambda/-bromosuccinimide (8.36 g, 47.0 mmol) and then benzoyl peroxide (1.03 g, 4.27 mmol). The mixture is stirred in oil bath at 60 0C under heat lamp for 5 h. The mixture is then cooled to room temperature. About half of the solvent is removed by rotary evaporation. The white succinimide solid is removed by filtration. The overweight filtrate (17 g for a theoretical 13.4 g, 42.7 mmol) is concentrated under reduced pressure and used as a crude immediately for the next step. MS(ESI) m/z 313.99. 1H NMR (400 MHz1CDCI3) delta ppm 7.72 (s, 1 H), 4.99 (s, 2 H), 4.48 (q, J=7.16 Hz, 2 H), 1.46 (t, J=7.07 Hz, 3 H).

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. 137520-99-1, Ethyl 2,6-dichloro-3-methylisonicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; WO2009/150230; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1187322-51-5, 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. 1187322-51-5, name is 6-Amino-5-iodonicotinonitrile, molecular formula is C6H4IN3, 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.

1.2 g 5-[4-(6-trimethylsilanyl-hex-5-ynyl)-piperazin-1-yl]-benzofuran-2- carboxylic acid amide, 500 mg beta-amino-delta-iodo-nicotinonitrile, 0.1 g lithium chloride, 0.8 g sodium carbonate and 0.1 g 1,1′-bis(diphenyl- phosphino)ferrocenedichloropalladium- (II) dichloromethane adduct were dissolved in 50 ml DMF and heated for 12 h. The black suspension was poured on 50 ml water and extracted with ethyl acetate. After the usual extraction and purification procedure 20 mg of fawn amorphous solid 5-{4-[4-(5-cyano-1 H-pyrrolo[2,3-b]pyridine-3-yl)-butyl]- piperazin-1-yl}-benzofuran-2-carboxylic acid amide were obtained. 1H-NMR (500MHz, dbeta-DMSO) delta 12.18 (br s, 1H)1 8.49 (d, 1 H, J = 1.8 Hz), 8.33 (d, 1 H, J = 1.8 Hz), 7.99 (br. s, 1 H), 7.57 (br. s, 1 H), 7.47 (d, 1H1 J = 9.9 Hz), 7.40 (s, 1 H), 7.17 (m, 2H), 6.35 (s, 1 H), 3.33 (m, 4H), 3.11 (m, 4H)1 2.81 (m, 2H), 2.38 (m, 2H), 1.76 (m, 2H), 1.54 (m, 2H). P08033 HN.doc27HPLC-MS: Chromolite SpeedROD RP-18e 50-4, 6 mm solvent A: water + 0.1 % TFA solvent B: acetonitrile + 0.1% TFA 5 flow: 2.4 mL/min gradient: 0,0 min 4% B2.6 min 100% B Rt: 1.909 min[M+H]+: 398

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 1187322-51-5, 6-Amino-5-iodonicotinonitrile.

Reference:
Patent; MERCK PATENT GMBH,; WO2009/112139; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem