Tag: M.W:100-200

Reference of 81803-60-3, 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.81803-60-3, name is Ethyl imidazo[1,5-a]pyridine-3-carboxylate, molecular formula is C10H10N2O2, molecular weight is 190.2, as common compound, the synthetic route is as follows.

To a solution of ethyl imidazo[1,5-a]pyridine-3-carboxylate (152 mg) in Acetic Acid (0.25M) was added Bromine (leq). The reaction was stirred at room temperature for 5 minutes thenconcentrated to dryness to give 205 of the title compound. This intermediate was taken onto the next step without purification.

The chemical industry reduces the impact on the environment during synthesis 81803-60-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; BURCH, Jason; CASTANEDO, Georgette; FENG, Jianwen A.; HU, Baihua; STABEN, Steven; WU, Guosheng; YUEN, Po-wai; WO2015/25025; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 56057-19-3 , The common heterocyclic compound, 56057-19-3, name is 6-Chloro-5-nitro-2-picoline, molecular formula is C6H5ClN2O2, 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.

C. 2-Phenyl-5-nitro-6-methylpyridine A mixture of Compound B and 2-chloro-3-nitro-6-methylpyridine (0.42 g, 2.40 mmol) in THF (10 mL) was degassed with nitrogen. Tetrakistriphenylphosphine palladium (28 mg, 0.024 mmol) was added and the mixture was stirred 30 minutes. 25 Phenylboronic acid (0.44 g, 3.6 mmol) and 2M Na2 CO3 (1.8 mL) were added and the mixture was heated at 75 C. for 17 hours and stirred at room temperature for 48 hours. Methylene chloride was added and the mixture was filtered through celite and partitioned. The mixture was washed with saturated aqueous NaHCO3, dried (magnesium sulfate), filtered and evaporated to afford 0.77 g of brown solid. Flash chromatography (silica, 10% ethyl acetate/hexanes) afforded 0.37 g of Compound C (72%) as an off white solid and 0.05 g of 2-phenyl-3-nitro-6-methylpyridine (10%) as an oil.

The synthetic route of 56057-19-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US6011029; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 696-42-4, 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 696-42-4, name is 5-Fluoronicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows.

[0307] Cesium carbonate (0.734 g, 2.25 mmol) and 5-chloro-3-methylpyridine-2-carbonitrile (0.206 g, 1.35 mmol) wereadded at room temperature to a suspension of the optically active form of cis-1-(diphenylmethyl)-5-hydroxy-3-(piperidin-4-yl)-4-(trifluoromethyl)-1,4,5,7-tetrahydro-6H-pyrazolo[3,4-b]pyridin-6-one (0.212 g, 0.451 mmol) produced in ReferenceExample 27 in DMSO (2 mL), and the mixture was stirred at 150C for 2 hours. The reaction suspension wascooled to room temperature, then diluted with ethyl acetate, and washed with brine. The obtained organic layer wasdried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residuewas purified by silica gel column chromatography [elute: hexane/ethyl acetate = 92/8 – 50/50 (gradient)] to obtain thetitle compound (0.226 g, yield: 86%, optically active form:_[0327] The title compound (42.7 g, yield: 70%, optically active form) was obtained through reaction at 80C for 1 hourand then at 100C for 5 hours by the method described in Reference Example 30 using 5-fluoropyridine-3-carbonitrile(26.0 mg, 0.213 mmol) instead of 5-chloro-3-methylpyridine-2-carbonitrile.[0328] 1H-NMR (400MHz, CDCl3) delta: 8.46 (1H, d, J=3Hz), 8.25 (1H, d, J=2Hz), 7.43-7.04 (10H, m), 6.91 (1H, s), 6.71(1H, s), 4.56-4.51 (1H, m), 3.96-3.86 (1H, m), 3.83-3.73 (2H, m), 3.72-3.67 (1H, m), 3.02-2.93 (2H, m), 2.87-2.76 (1H,m), 2.08-1.85 (4H, m).

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 696-42-4, 5-Fluoronicotinonitrile.

Reference:
Patent; Daiichi Sankyo Company, Limited; KOBAYASHI, Hideki; ARAI, Masami; KANEKO, Toshio; TERASAKA, Naoki; (95 pag.)EP3081566; (2016); A1;,
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.79055-59-7, name is 2-Bromo-6-methylpyridin-4-amine, molecular formula is C6H7BrN2, molecular weight is 187.04, as common compound, the synthetic route is as follows.name: 2-Bromo-6-methylpyridin-4-amine

Lithium bis(trimethylsilyl)amide in THF (4.63 mL, 1 M, 4.63 mmol) was added to ethyl 3-fluoro- 1 -methyl-4-[[ 1 -(trifluoromethyl)cyclobutyl]sulfamoyl]pyrrole-2-carboxylate (492.4 mg, 1.322 mmol) and 2-bromo-6-methylpyridin-4-amine (371.0 mg, 1.98 mmol) in THF (4 mL) and the mixture was stirred for 1 hour. The reaction mixture was quenched with a saturated aqueous NH4CI solution, diluted with brine and extracted with EtOAc. The organic layer was dried over magnesium sulphate, filtered and concentrated. The residue was purified by column (0775) chromatography using a gradient from 10 till 100% EtOAc in heptane. The obtained solid was dissolved in methanol (40 mL) and water was added untill crystallisation began. The product was filtered off and dried overnight in vacuo at 50C resulting in compound 164 (534 mg) as a white powder. Method D: Rt: 1.98 min. m/z: 511.1 (M-H)~ Exact mass: 512.0. DSC: From 30 to 300 C at 10C/min, peak 202.4 C. 1H NMR (400 MHz, ACETONITRILE-d3) delta ppm 1.85 – 1.93 (m, 2 H), 2.36 – 2.46 (m, 5 H), 2.47 – 2.57 (m, 2 H), 3.86 (s, 3 H), 6.48 (br. s, 1 H), 7.25 (d, J=4.8 Hz, 1 H), 7.42 (d, J=1.5 Hz, 1 H), 7.73 (d, J=1.5 Hz, 1 H), 8.47 (br. s, 1 H). 1H NMR (400 MHz, DMSO-d6) delta ppm 1.79 – 1.91 (m, 2 H), 2.27 – 2.38 (m, 2 H), 2.39 – 2.49 (m, 5 H), 3.82 (s, 3 H), 7.52 (d, J=1.3 Hz, 1 H), 7.57 (d, J=4.4 Hz, 1 H), 7.77 (d, J=l . l Hz, 1 H), 8.73 (s, 1 H), 10.46 (s, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,79055-59-7, 2-Bromo-6-methylpyridin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN SCIENCES IRELAND UC; VANDYCK, Koen; HACHE, Geerwin Yvonne Paul; LAST, Stefaan Julien; ROMBOUTS, Geert; VERSCHUEREN, Wim Gaston; RABOISSON, Pierre Jean-Marie Bernard; WO2015/118057; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 79456-33-0, 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.79456-33-0, name is 5-Chloro-3-(trifluoromethyl)pyridin-2-amine, molecular formula is C6H4ClF3N2, molecular weight is 196.56, as common compound, the synthetic route is as follows.

To a stirred solution of 5-chloro-3-(trifluoromethyl)pyridin-2-amine (Intermediate 47; CAS79456-33-0, 10 g, 50.9 mmol) in aqueous HBr (48 %, 56.7 g, 336 mmol) at -10 C wasadded bromine (23.6 g, 147.5 mmol) dropwise over 20 minutes, followed by a solution ofsodium nitrite (10.2 g, 147.8 mmol) in water (18 mL). The reaction was stirred at ambienttemperature for 2 hours and was basified (pH 9-10) and extracted into diethyl ether. Theorganic was washed with brine, dried (Na2504), filtered and concentrated in vacuo toafford the title compound without further purification.MS ES: 262

The chemical industry reduces the impact on the environment during synthesis 79456-33-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; TAKEDA CAMBRIDGE LIMITED; TAKEDA PHARMACEUTICAL COMPANY LIMITED; GOLDBY, Anne; JENKINS, Kerry; TEALL, Martin; WO2015/79224; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 197376-47-9, 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. 197376-47-9, name is Ethyl 6-Chloropyridine-3-acetate, molecular formula is C9H10ClNO2, 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 solution of (E)-3-ethyl-1-(4-{1-ethyl-1-[4-(4,4,5,5-tetramethyl-[1, 3, 2] dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenyl)-1-penten-3-ol (Example 39-(5); 50.0 mg, 0.10 mmol), (6-chloro-pyridin-3-yl)acetic acid ethyl ester (31.4 mg, 0.15 mmol), tetrakistriphenylphosphine palladium (16.9 mg, 0.0146 mmol) and potassium phosphate (33.4 mg, 0.15 mmol) in N,N-dimethylformamide (0.30 mL) was stirred with microwave heating at 140C for 10 minutes. The reaction mixture was filtered through cotton plug, and the residue was purified by silica gel chromatography (30 to 40% ethyl acetate/hexane) to give the title compound (37.6 mg, 69%). 1H-NMR (chloroform-d): 0.65 (t, 6H, J=7.3Hz), 0.92 (t, 6H, J=7.3Hz), 1.26 (t, 3H, J=7.1Hz), 1.64 (q, 4H, J=7.5Hz), 2.13 (q, 4H, J=7.2Hz), 2.30 (s, 3H), 3.64 (s, 2H), 4.18 (q, 2H, J=7.1Hz), 6.01 (d, 1H, J=16.1Hz), 6.75 (d, 1H, J=16.1Hz), 6.96-6.99 (m, 2H), 7.26-7.32 (m, 3H), 7.68 (s, 2H), 7.85 (d, 2H, J=8.4Hz), 8.56 (s, 1H).

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 197376-47-9, Ethyl 6-Chloropyridine-3-acetate.

Reference:
Patent; CHUGAI SEIYAKU KABUSHIKI KAISHA; EP1894911; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 94220-38-9 , The common heterocyclic compound, 94220-38-9, name is 7-Chloro-5-methyl-1H-pyrazolo[4,3-b]-pyridine, molecular formula is C7H6ClN3, 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.

EXAMPLE 9 7-(3-Dimethylaminopropylamino)-5-methyl-1H-pyrazolo[4,3-b]pyridine hydrochloride, monohydrate (E9) STR23 A mixture of 7-chloro-5-methyl-1H-pyrazolo[4,3-b]pyridine (D4) (19.21 g, 0.115 mole) and 3-dimethylaminopropylamine (100 g) in xylene (770 ml) was heated at reflux under nitrogen for 83 h. After allowing to cool to room temperature, volatile material was removed under reduced pressure. The residue, an orange oil, was treated with ether and methanol and then left to stand at 4 C. overnight. The resulting pale yellow crystalline solid was collected, washed with ether/methanol and dried under vacuum to give the title compound (12.5 g, 38%), m.p. 183-186 C. (Found: C,50.29; H,7.53; N,24.44. C12 H19 N5.HCl.H2 O requires: C,50.08; H,7.69; N,24.34%). delta(DMSO-d6) 1.88-2.05 (2H,m); 2.47 (3H,s); 2.53 (6H,s); 2.82-2.95 (2H,m); 3.32-3.47 (2H,m); 6.37 (1H,s); 7.9 (1H, brs); 8.01 (1H, s);

The synthetic route of 94220-38-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beecham Group p.l.c.; US4670432; (1987); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1019021-85-2, 6-Fluoroimidazo[1,2-a]pyridine-3-carboxylic acid, 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, 1019021-85-2, blongs to pyridine-derivatives compound. SDS of cas: 1019021-85-2

Oxalyl chloride (10 mL, 110 mmol) was added dropwise to a stirred suspension of 6-fluoroimidazo[1,2-a]pyridine-3-carboxylic acid (24b) (2 g, 11 mmol) and catalytic amounts of DMF in dichloromethane (20 mL). After 5 hours, the solvent was evaporated and the solid was suspended in dry DCE (20 mL) and added to a stirred solution of 3-amino-4-methylbenzonitrile (1.45 g, 11 mmol) and DIEA (6 mmol) in DCE (10 mL) at 0 C. After the addition, the reaction was heated at 60 C. for 5 hours. The mixture was subjected to standard aqueous work and silica purification to give N-(5-cyano-2-methylphenyl)-6-fluoroimidazo[1,2-a]pyridine-3-carboxamide (39) as a solid. 1H NMR (400 MHz, d6-DMSO) delta 10.14 (s, 1H), 9.45 (dd, J=5.2, 2.0 Hz, 1H), 8.62 (s, 1H), 7.90-7.87 (m, 2H), 7.68-7.63 (m, 1H), 7.53 (d, J=8.0 Hz, 1H), 2.37 (s, 3H). MS m/z 295.1 (M+1)+.; NH2OH (5 mL, 16.1 mmol) was added in one portion to a stirred suspension of N-(5-cyano-2-methylphenyl)-6-fluoroimidazo[1,2-a]pyridine-3-carboxamide (39) (0.95 g, 3.23 mmol). The resulting suspension was heated at 60 C. overnight and then cooled to 0 C. The product, (Z)-6-fluoro-N-(5-(N?-hydroxycarbamimidoyl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (40) was collected by filtration. MS m/z 328.1 (M+1)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1019021-85-2, its application will become more common.

Reference:
Patent; IRM LLC; YEH, Vince; LI, Xiaolin; LIU, Xiaodong; LOREN, Jon; MOLTENI, Valentina; NABAKKA, Juliet; NGUYEN, Bao; PETRASSI, Hank Michael James; US2013/59846; (2013); A1;,
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. 32710-65-9, name is 2,6-Dichloroisonicotinonitrile, molecular formula is C6H2Cl2N2, 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. Safety of 2,6-Dichloroisonicotinonitrile

Synthesis of 2-chloro-6-methoxy-pyridine-4-carbonitrile 25F A solution of compound 24 (2.0 g, 1 1.6 mmol) in methanol (20 mL) was added with sodium methoxyde (628 mg, 1 mol eq) and the mixture was heated at 60C for 6h. The reaction was cooled, evaporated to dryness and then water was added (300 mL). The aqueous phase was extracted with EtOAc (3×25 mL) and the recombined organic phases were dried over sodium sulfate and evaporated under reduced pressure to afford 25F as transparent viscous oil (1.95g, quantitative yield). FontWeight=”Bold” FontSize=”10″ HNMR (DMSO, 200 MHz) delta 3.80 (s, 3H), 7.17 (s, 1H), 7.90 (s, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 32710-65-9.

Reference:
Patent; PHARMESTE S.R.L. IN LIQUIDATION; FRUTTAROLO, Francesca; PAVANI, Maria Giovanna; BENCIVENNI, Serena; GATTI, Raffaele; NAPOLETANO, Mauro; WO2014/135617; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 442129-37-5, 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.442129-37-5, name is 6-Chloro-5-methylpyridin-2-amine, molecular formula is C6H7ClN2, molecular weight is 142.59, as common compound, the synthetic route is as follows.

3.4 g of chloride IA was added to 10 ml of phosphorus tribromide and heated to 140 degrees.After 6 hours of reaction, the TLC reaction was complete, dropped to ambient temperature, and slowly added to crushed ice.Add 40% sodium hydroxide to adjust the pH to 10, a large amount of solids are precipitated, filtered, and the filter cake is washed with 20 ml of water.The product IB 4g was obtained in a yield of 91%.

Statistics shows that 442129-37-5 is playing an increasingly important role. we look forward to future research findings about 6-Chloro-5-methylpyridin-2-amine.

Reference:
Patent; Shandong Tefaman Pharmaceutical Co., Ltd.; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Jiang Xiangrui; Chen Hua; Zhang Junchi; Shen Jingshan; (10 pag.)CN108658851; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem