Tag: M.W:100-200

5470-18-8, 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. 5470-18-8, name is 2-Chloro-3-nitropyridine, molecular formula is C5H3ClN2O2, 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.

Step 1 : A mixture of 2-chloro-3-nitropyridine (5.0 g, 31.5 mmol) and aniline (5.8 mL, 63.1 mmol) was heated to 140C for 90 minutes. After cooling to ambient temperature, the mixture was diluted with water (200 mL) and extracted with three portions (50 mL each) of dichloromethane. The combined extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude solids were recrystallized from isopropyl alcohol to afford 3.50 g of 3-nitro-N-phenylpyridin-2-amine.HRMS: calculated for C11H9N3O2 + H+, 216.07675; found (ESI, [M+H]+), 216.0787HPLC purity 100.0% at 210-370 nm, 9.5 minutes.; Xterra RP18, 3.5u, 150 x 4.6 mm column,1.2 mL/min, 85/15-5/95 (ammonium formate buffer pH=3.5, acetonitrile/MeOH) for 10 minutes, hold 4 minutes.

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. 5470-18-8, 2-Chloro-3-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WYETH; WO2008/73459; (2008); 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. 7379-35-3, name is 4-Chloropyridine hydrochloride. A new synthetic method of this compound is introduced below., 7379-35-3

N-t-butoxycarbonyloxy 2- (piperidin-4-yl)-ethylamine (prepared per Method K’above) (14.4 g, 50 mmol), 4-chloropyridine HC1 (1.0 eq. , 8.0 g), TEA (2.2 eq. ) were mixed in ethanol, and maintained under reflux overnight. The desired compound, N-t-butoxycarbonyloxy 2- [1- (pyrid-4-yl) piperidin-4-yl] – ethylamine, was isolated by column chromato-graphy, (silica gel) eluted with EtOAc and carried in the next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7379-35-3, 4-Chloropyridine hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2003/93245; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

766-11-0, 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. 766-11-0, name is 5-Bromo-2-fluoropyridine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of alcohol 1a-r or benzyl mercaptan 1s (1.5 equiv.) in anhydrous THF (100 mL) was slowly added 60% sodium hydride (2.0 equiv.). The mixture was allowed to react at room temperature for 30 min then it was heated to reflux for 1 h. 5-bromo-2-fluoropyridine (1 equiv.) was added and the reaction was continued for 12 h. After cooling down to room temperature, the mixture was poured into water and extracted with ethyl acetate. The organic phase was washed with brine, dried on MgSO4, filtered, evaporated and purified by silica gel chromatography.

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 766-11-0, 5-Bromo-2-fluoropyridine.

Reference:
Article; Fontaine, Fanny; Hequet, Arnaud; Voisin-Chiret, Anne-Sophie; Bouillon, Alexandre; Lesnard, Aurelien; Cresteil, Thierry; Jolivalt, Claude; Rault, Sylvain; European Journal of Medicinal Chemistry; vol. 95; (2015); p. 185 – 198;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

100-26-5, 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 100-26-5, name is 2,5-Pyridinedicarboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Three series of [Ln2(pydc)2(SO4) (H2O)x]yH2O (x= 0, 2, 3; y= 0, 2,6), differing in numbers of the coordinated (x) and the crystallizing (y) water molecules, were hydrothermally synthesized through subtlealteration in reaction temperature and time (Scheme 1). [Ln2(pydc)2(SO4) (H2O)2]6H2O; LnLa (Ia), Pr (Ib), Nd (Ic). To synthesize Ia, a solution of La2(SO4)38H2O (0.1420 g, 0.2000 mmol) and H2pydc (0.0334 g, 0.200 mmol) was prepared using 10.00 ml of deionized water, into which 50.0 muL triethylamine was added to adjust pH of the solution to 5. The solution was then transferred into a 23mL Teflon lined hydrothermal reactor, which was then sealed and heated at two different temperatures, i.e. 80 and 120 C, for 1 day. After the reaction was cooled down to room temperature, colorless block crystals of Ia was obtained in ca. 35% yield based on LaIII.

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 100-26-5, 2,5-Pyridinedicarboxylic acid.

Reference:
Article; Sinchow; Chuasaard, Thammanoon; Yotnoi, Bunlawee; Rujiwatra, Apinpus; Journal of Solid State Chemistry; vol. 278; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

74115-13-2, A common compound: 74115-13-2, name is 5-Bromo-3-pyridinol,molecular formula is C5H4BrNO, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

To a solution of 5-bromopyridin-3-ol (L) (174 mg, 1.0 mmol) in DMF (3 mL) was added potassium carbonate (415 mg, 3.0 mmol). The slurry was heated at 90C for 1 h and then cooled to 25 C. The (bromomethyl)benzene (LIV) (171 mg, 1.0 mmol) was added and the mixture was stirred at 25C overnight. The reaction was worked-up using a saturated sodium bicarbonate and EtOAc extraction. The product was purified by ISCO column (40-100% EtOAc- hexanes). The 3-(benzyloxy)-5-bromopyridine (LV) (105 mg, 0.398 mmol, 39.8 % yield) was obtained as yellow oil. ESIMS found for Ci2Hi0BrNO mlz 266.1 (M+H).

With the rapid development of chemical substances, we look forward to future research findings about 74115-13-2.

Reference:
Patent; SAMUMED, LLC; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (251 pag.)WO2017/24003; (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. 117519-09-2, name is 3-Amino-2-chloro-6-(trifluoromethyl)pyridine. A new synthetic method of this compound is introduced below., 117519-09-2

A mixture of 2-chloro-6-(trifluoromethyl)pyridin-3-amine (5.0 g, 25.44 mmol), 4,4,5,5-tetramethyl-2-(prop-l-en-2-yl)-l,3,2-dioxaborolane (4.7 g, 27.98 mmol), Pd(dppf)Cl2 (1.86 g, 2.54 mmol) and K2C03 (8.79 g, 63.59 mmol) in l,4-dioxane (50 mL) and H20 (10 mL) was stirred at 80C for 7 hours under a nitrogen atmosphere. After cooling to room temperature, the reaction mixture was concentrated. The crude residue was purified by silica gel column chromatography (0-10% EtOAc in petroleum ether) to give 3-nitro-2-(prop-l-en-2-yl)-6- (trifluoromethyl)pyridine (4.68 g, yield: 91% ) as a light yellow solid. 1H NMR (400 MHz, CDCl3) d = 7.34, (d, J= 8.4 Hz, 1H), 7.03 (d, J= 8.4 Hz, 1H), 5.54-5.53 (m, 1H), 5.36-5.34 (m, 1H), 4.22 (s, 2H), 2.18 (s, 3H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,117519-09-2, 3-Amino-2-chloro-6-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; GENENTECH, INC.; STAFFORD, Jeffrey, A.; VEAL, James, M.; TRZOSS, Lynnie, Lin; MCBRIDE, Christopher; PASTOR, Richard, M.; STABEN, Steven, Thomas; STIVALA, Craig; VOLGRAF, Matthew; (200 pag.)WO2020/18970; (2020); 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 586-95-8, name is 4-Pyridinemethanol. This compound has unique chemical properties. The synthetic route is as follows. 586-95-8

Dissolve 4-pyridinemethanol (200 mg, 1.83 mmol) in 2 ml of dichlorosulfoxide. After heating to 70 C. for 1 h, concentrate to remove dichlorosulfoxide under reduced pressure to obtain compound 39b

Statistics shows that 586-95-8 is playing an increasingly important role. we look forward to future research findings about 4-Pyridinemethanol.

Reference:
Patent; Sichuan University; Li Guobo; Wang Zhenling; (40 pag.)CN111187218; (2020); A;,
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. 1003-68-5, name is 5-Methylpyridin-2(1H)-one. A new synthetic method of this compound is introduced below., 1003-68-5

A mixture of 5 -methyl- lH-pyridin-2-one (100 g), bromo benzene (259 g, comprising greater than 0.2% by weight dibromobenzene isomers) and dimethylformamide (200 ml) were added in to a round bottom flask and stirred up to complete dissolution. Potassium carbonate (254 g) and copper (I) chloride (18.2 g) was added to the above reaction mass and then heated to 130-140C. The reaction mass was stirred at 130-140C for 10 hrs. After the reaction completion, the reaction mass was cooled to 25-35C. Toluene (500 ml), aqueous sodium chloride (75 g of sodium chloride in 500 ml of water) was added to the reaction mass and stirred for 15-30 mins at 25-35C. The reaction mass was filtered and the filtrate was allowed to settle. Organic and aqueous layers were separated and the aqueous layer was extracted with toluene. Organic layers combined and was washed with aqueous sodium chloride, treated with carbon and filtered through hyflo. The solvent from the filtrate was distilled off completely under vacuum at below 60C. Toluene (300 ml) was added to the obtained residue and stirred for 30 mins. The reaction mass was heated to 77-83C and stirred for 45 mins. The reaction mass was cooled to 25-35C over 60 mins. The reaction mass was further cooled to 0-6C. The solid obtained was filtered, washed with toluene and dried under vacuum. DM water (500 ml) was added to the above obtained wet compound followed by 50% aqueous sodium hydroxide solution (10 g of sodium hydroxide in 20 ml of water) at 25-35C. The reaction mass was heated to 75-85C and stirred for 30-60 mins. The reaction mass was then gradually cooled to 25-35C and stirred for 60 mins. The reaction mass was further cooled to 0-5 C and stirred for 3 hrs. The obtained solid was filtered, washed with water and dried to provide the title compound.Yield: 120 g; purity by HPLC: 99%; The XRPD is set forth in Figure 1 The DSC is set forth in Figure 2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1003-68-5, 5-Methylpyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; LAURUS LABS LIMITED; BOLLU, Ravindra Babu; MANDADAPU, Venkata Pramod Kumar; INDUKURI, Venkata Sunil Kumar; CHAVA, Satyanarayana; (20 pag.)WO2017/122139; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

1721-12-6, 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. 1721-12-6, name is 1-(2-Methylpyridin-3-yl)ethanone, molecular formula is C8H9NO, 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.

Step B. 3-Chloroacetyl-2-methylpyridine hydrochloride. To 2.25 g (16.6 mmol) of the ketone from Step A dissolved in 20 mL of ethyl ether was added 20 mL of 1.0 M hydrogen chloride in ethyl ether, resulting in a pale yellow slurry. After 30 min, the precipitate was filtered and washed with ethyl ether. After drying in vacuo, 2.80 g (16.3 mmol) of a pale yellow powder was obtained. This material was dissolved in 15 mL of a solution of 1.0 M hydrogen chloride in acetic acid and treated with 2.18 g (16.3 mmol) of N-chlorosuccinimide. After six days, the reaction mixture was concentrated in vacuo, and the resultant pale yellow residue solidified on standing. This material was triturated with 20% acetic acid/ethyl ether, (3*50 mL) to afford 2.62 g of a white powder, 77% yield. The 1H NMR spectra of this compound appears as a rotameric mixture (65:35, rotamer A: rotamer B): 1H NMR (CDCl3) delta: 9.16, (d, J=2.0 Hz, 1H, rotamer A), 8.84, (dd, J=2.0, 8.4 Hz, 1H, rotamer A), 8.64, (d, J=2.0 Hz, 1H, rotamer B), 8.50, (dd, J=2.0, 8.4 Hz, 1H, rotamer B), 7.96, (d, J=8.4 Hz, 1H, rotamer A), 7.86, (d, J=8.4 Hz, 1H, rotamer B), 4.93, (s 1H, rotamer A), 3.74, (2d, J=11.8 Hz, 2H, rotamer B), 2.77, (s 1H, rotamer A), 2.72, (s 1H, rotamer B).

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. 1721-12-6, 1-(2-Methylpyridin-3-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck & Co., Inc.; US6291491; (2001); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6419-36-9, 2-(Pyridin-3-yl)acetic acid hydrochloride, 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, 6419-36-9, blongs to pyridine-derivatives compound. 6419-36-9

HATU (41.6 mg, 0.11 mmol) was added to a solution of DIEA (0.048 mL, 0.27 mmol), 2-(pyridin-3-yl)acetic acid hydrochloride (18.98 mg, 0.11 mmol) and (R)-N-(3,5-difluoro-4-(2-methyl-1-oxo-1-(pyrrolidin-1-yl)propan-2-yl)phenyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxamide hydrochloride (45 mg, 0.09 mmol) in DMF (2 mL) at room temperature, and the mixture was stirred overnight at room temperature. To the reaction mixture was added aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 0?25% MeOH/ethyl acetate) to give the title compound (33.0 mg, 0.057 mmol, 62.8%) as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6419-36-9, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; YAMAMOTO, SATOSHI; SHIRAI, JUNYA; WATANABE, HIROYUKI; FUKUMOTO, SHOJI; ODA, TSUNEO; TOKUHARA, HIDEKAZU; TOMATA, YOSHIHIDE; ISHII, NAOKI; TAWADA, MICHIKO; KOUNO, MITSUNORI; OCHIDA, ATSUKO; IMADA, TAKASHI; FUKASE, YOSHIYUKI; YUKAWA, TOMOYA; (719 pag.)TW2016/2105; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem