Tag: M.W:200-300

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.887707-23-5, name is 2-Hydroxy-5-iodo-3-(trifluoromethyl)pyridine, molecular formula is C6H3F3INO, molecular weight is 288.9938, as common compound, the synthetic route is as follows.HPLC of Formula: C6H3F3INO

Step 2:; The phenol 5a2 (125 g, 424 mmol) is placed in a 3-neck 2 L flask. Phenylphosphonic dichloride (500 mL) is added and the mixture heated to 136C under Ar with stirring. After consumption of starting material (about 4-5 h), the reaction is cooled to RT and carefully quenched by the slow addition of the reaction mixture to crushed ice (caution: very exothermic.). A white solid forms which is filtered. The solid is dissolved in EtOAc (2 L) and aqueous NaOH is added with stirring. A NaOH solution is added until the aqueous layer is neutral. The EtOAc layer is separated, washed with water and brine and dried over anhydrous Na2SO4. Removal of solvent gives a white solid which is washed with cold hexane to afford chloride5a3

At the same time, in my other blogs, there are other synthetic methods of this type of compound,887707-23-5, 2-Hydroxy-5-iodo-3-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; WO2009/76747; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 849068-61-7, Adding some certain compound to certain chemical reactions, such as: 849068-61-7, name is 5-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid,molecular formula is C8H5BrN2O2, 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 849068-61-7.

To a mixture of 5-bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid (20 g, 82.99 mmol) in MeOH (200 mL) was added SOCl2 (30ml) dropwise at room temperature. After addition, the resulting mixture was heated to 70 C and stirred overnight. TLC (EtOAc) showed the reaction was completed. The solvent was removed in vacuo and then aqueous NaHCO3 (20 mL) was added at which time a precipitate formed. The solid was filtered and dried to give methyl 5-bromo-1H-pyrrolo[2,3-b]pyridine-3- carboxylate (15.3g, 72.3%) as a brown solid.

According to the analysis of related databases, 849068-61-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; THORARENSEN, Atli; BROWN, Matthew Frank; CASIMIRO-GARCIA, Agustin; CHE, Ye; FLANAGAN, Mark Edward; GILBERT, Adam Matthew; HAYWARD, Matthew Merrill; TELLIEZ, Jean-Baptiste; UNWALLA, Rayomand Jal; TRUJILLO, John I.; LIANG, Sidney Xi; (212 pag.)WO2016/178110; (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.936342-91-5, name is 5-Bromo-2-(chloromethyl)pyridine hydrochloride, molecular formula is C6H6BrCl2N, molecular weight is 242.9285, as common compound, the synthetic route is as follows.Safety of 5-Bromo-2-(chloromethyl)pyridine hydrochloride

The title compound was prepared by the reaction of 2-butyl-l,3-diazaspiro[4.4]non-l-en- 4-one.HCl (0.250 g, 1.083 mmol) with 5-bromo-2-(chloromethyl)pyridine.HCl (0.263 g, 1.083 mmol), according to the method described for the synthesis of Intermediate 451a, to give a white solid (0.300 g, 76percent). LC-MS (Method H): 1.23 min, [M + H]+= 364.0; H NMR (DMSO-i) 5 ppm 8.63 (dd, / = 2.3, 0.8 Hz, 1H), 8.04 (dd, / = 8.2, 2.3 Hz, 1H), 7.24 (d, / = 8.2 Hz, 1H), 4.75 (s, 2H), 2.25 – 2.41 (m, 2H), 1.71 – 1.94 (m, 6H), 1.56 – 1.71 (m, 2H), 1.43 – 1.56 (m, 2H), 1.27 (dq, / = 15.0, 7.4 Hz, 2H), 0.81 (t, / = 7.2 Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,936342-91-5, 5-Bromo-2-(chloromethyl)pyridine hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; UNIVERSITE DE MONTREAL; BRISTOL-MYERS SQUIBB COMPANY; PRIESTLEY, Eldon, Scott; REZNIK, Samuel, Kaye; RUEDIGER, Edward, H.; GILLARD, James, R.; HALPERN, Oz, Scott; JIANG, Wen; RICHTER, Jeremy; RUEL, Rejean; TRIPATHY, Sasmita; YANG, Wu; ZHANG, Xiaojun; (642 pag.)WO2018/5591; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 64690-19-3, 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 64690-19-3 as follows.

B. A mixture of 4-octylaminopyridine (25 g., 0.121 mole) and octyl chloride (20.5 ml., 0.121 mole) was heated at 180 C. for 1 hr. More octyl chloride (0.5 ml.) was added and the mixture was again heated at 180 C. for 1 hr., then dissolved in dichloromethane. The dichloromethane solution was treated with charcoal, filtered, and stripped of solvent under vacuum. The solid residue was slurried in ether (1.5 kg.), collected by filtration, washed with ether (500 g.), isolated in a dry bag, and dried (50-80 C., 0.1 mm.). The procedure was repeated using the same amounts of starting materials and the product were combined, affording N-(1-octyl-4(1H)-pyridinylidene)octanamine monohydrochloride (80.5 g., 93% yield, m.r. 120-125 C.), which is the monohydrochloride salt of the compound of Formula I wherein R and R’ are both octyl.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,64690-19-3, its application will become more common.

Reference:
Patent; Sterling Drug Inc.; US4839372; (1989); A;,
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. 6945-67-1, name is 2-Bromo-4-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. name: 2-Bromo-4-nitropyridine

[ STEP C] To a mixture of 234 (6g, 0. 029mol), [PDCL2] (Ph3) 2 (620mg, 3 mol%), Cul (338mg, 6 mol%) under an atmosphere of nitrogen was added diisopropylethylamine (100 mL). The resulting mixture was stirred at ambient temperature for several minutes before the introduction of TMS acetylene (6. 3ml, [1.] [5EQUIV).] The contents were then heated at [60C] for 24 hours. The solvent was removed under reduced pressure and the crude material filtered through silica gel column (hexanes: EtOAc 10: 1) to give 236 as a yellow solid, 4.9 gm [(76%).]

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, 6945-67-1, 2-Bromo-4-nitropyridine.

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; WO2004/18463; (2004); A2;,
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. 1072438-56-2, name is Methyl 6-(aminomethyl)nicotinate hydrochloride, the common compound, a new synthetic route is introduced below. Computed Properties of C8H11ClN2O2

Intermediate 8: methyl 6-(f r(4-chlorophenyl)sulfonyllaminolmethyl)nicotinate A cooled (0 0C) solution of methyl-6-aminomethyl pyridine-3-carboxylate.HCI (700 mg; 3.45 mmol) and triethylamine (0.96 ml; 6.91 mmol) in DCM (14 ml) was treated with a solution of4-chlorobenzenesulfonyl chloride (729 mg; 3.45 mmol) in DCM (10 mL). After stirring for 20 h, the mixture was diluted with DCM and washed with water and sat. NaHCO3 solution. The organic phase was separated, dried over magnesium sulfate, filtered and concentrated to give solid, which was crystallised from DCM/Cyclohexane to afford the title compound as a grey solid (524mg, 45 %).1 H NMR (DMSO-c/6, 300MHz): 8 8.91 (1 H, d, J = 1 .5 Hz), 8.54 (1 H, t, J = 6.5 Hz), 8.23 (1 H, dd, J = 8.0 Hz, J = 2.0 Hz), 7.76 (2H, d, J = 8.5 Hz), 7.62 (2H, d, J = 8.5 Hz), 7.50 (1 H, d, J =8.0 Hz) 4.21 (2H, d, J = 6.5 Hz), 3.88 (3H, s). MS (ESI+): 341.1 . HPLC (Condition A): Rt 3.37 min (HPLC purity 97.7%).

The synthetic route of 1072438-56-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SERONO S.A.; WO2009/124962; (2009); A2;,
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. 17570-98-8, name is 2-(Bromoacetyl)pyridine hydrobromide, molecular formula is C7H7Br2NO, 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. name: 2-(Bromoacetyl)pyridine hydrobromide

[0284] 7V-(3-Methylphenyl)-4-(2-pyridinyl)-l,3-thiazol-2-amine (68). A mixture of bromoketone hydrobromide 67 (0.96 g, 3.4 mmol) and 3- methylphenylthiourea (4) (0.57 g, 3.4 mmol) in EtOH (25 mL) was stirred at reflux temperature for 3 h. The mixture was cooled to 20 0C, diluted with water (40 mL), the pH adjusted to ca. 8 with aqueous NH3 and the mixture stirred at 0 0C for 1 h. The precipitate was filtered, washed with water (5 mL) and dried. The crude solid was purified by column chromatography, eluting with EtOAc, to give amine 68 (0.74 g, 81%) as a cream powder: mp (EtOAc) 164-166 0C; 1H NMR delta 10.20 (br s, 1 H, NH), 8.58 (ddd, J= 4.7, 1.7, 0.8 Hz, 1 H, H-6′), 7.99 (dt, J= 7.9, 0.9 Hz, 1 H, H-3′), 7.99 (ddd, J= 7.9, 7.5, 1.8 Hz, 1 H, H-4′), 7.58 (br d, J= 8.1 Hz, 1 H, H- 6′), 7.52 (s, 1 H, H-5), 7.47 (br s, 1 H, H-2″), 7.31 (ddd, J= 7.5, 4.7, 1.2 Hz, 1 H, H-5′), 7.24 (t, J= 7.8 Hz, 1 H, H-5″), 6.80 (br d, J= 7.5 Hz, 1 H, H-4″), 2.33 (s, 3 H5 CH3); 13C NMR delta 163.3, 152.0, 150.2, 149.3, 141.0, 138.0, 137.1, 128.8, 122.4, 122.0, 120.2, 117.4, 114.0, 106.5, 21.2; MS m/z 268.4 (MH+, 100%). Anal, calcd for Ci5Hi3N3: C, 67.39; H, 4.90; N, 15.72. Found: C, 67.13; H, 5.10; N, 15.67%.

With the rapid development of chemical substances, we look forward to future research findings about 17570-98-8.

Reference:
Patent; THE BOARD OF TRUSTEES OF THE LELAND STANFORD JUNIOR UNIVERSITY; AUCKLAND UNISERVICES LIMITED; WO2009/114552; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 109613-97-0 ,Some common heterocyclic compound, 109613-97-0, molecular formula is C6H7BrN2O, 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 an ice-cold solution of 2-bromo-4-methoxypyridin-3-amine (Intermediate 38), (2.74 g) in pyridine (102 mL) was added ethyl chloroformate (1.91 mL) dropwise and then stirred at rt for 45 min. The reaction mixture was cooled in an ice-bath and more ethyl chloroformate (9 mL) added and the mixture left to stir overnight at rt. The reaction mixture was diluted with EtOAc and washed with sat. aq. NaHCO3. The aqueous layer was extracted with EtOAc and the combined organic layers washed with brine, dried over MgSO4, filtered and evaporated under vacuum to give a solid. Product was observed in the aqueous layer by LC-MS, so this was re-extracted with EtOAc (3*) and evaporated under vacuum to give a solid which was combined with the previous solid, dissolved in DCM and purified by column chromatography (normal phase, 50 g, Biotage SNAP cartridge KP-Sil, 50 mL/min, gradient 10-70% EtOAc in n-hexane) to give the desired product (2.35 g). LCMS: m/z 275.43 [M+H]+. 1H NMR (400 MHz, CDCl3) ppm 1.32 (t, J=7.1 Hz, 3H) 3.93 (s, 3H) 4.24 (q, J=7.1 Hz, 2H) 6.06 (br. s., 1H) 6.86 (d, J=5.6 Hz, 1H) 8.19 (d, J=5.6 Hz, 1H)

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. 109613-97-0, 2-Bromo-4-methoxypyridin-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; PAYNE, Andrew; CASTRO PINEIRO, Jose Luis; BIRCH, Louise Michelle; KHAN, Afzal; BRAUNTON, Alan James; KITULAGODA, James Edward; SOEJIMA, Motohiro; WO2015/49574; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 799293-73-5, 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 799293-73-5, name is 3-Bromofuro[3,2-c]pyridin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 4-iodo-1H-indazol-3-amine was replaced by 3-bromofuro[3,2-c]pyridin-4-amine and other raw materials, reagentsand preparation method were identical with those in step 6 of example 1. I-2 as yellow solid was obtained.1H NMR (300 MHz, DMSO-d6) delta (ppm): 5.68 (s, 2H), 7.02 (d, J = 6.0 Hz, 1H), 7.11-7.16 (m, 1H), 7.36-7.42 (m, 2H),7.66-7.71 (m, 1H), 7.76 (dd, J = 9.0, 1.8 Hz, 1H), 7.82-7.85 (m, 3H), 7.92 (d, J = 6.0 Hz, 1H), 8.13-8.19 (m, 3H), 8.34(d, J = 8.4 Hz, 1H), 10.62 (s, 1H).

According to the analysis of related databases, 799293-73-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Institute Of Materia Medica Chinese Academy of Sciences; DUAN, Wenhu; DING, Jian; LV, Yongcong; XIE, Hua; (54 pag.)EP3112351; (2017); 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. 17570-98-8, name is 2-(Bromoacetyl)pyridine hydrobromide, molecular formula is C7H7Br2NO, 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. category: pyridine-derivatives

Example 8; (S)-(4-Fluoro-phenyl)(3-(4-(pyridin-2-yl)-oxazol-2-yl)-piperidin-l-yl)-methanone; A solution of (S)-I -(4-fluoro-benzoyl)-piperidine-3-carboxylic acid amide (0.2 g, 0.8 mmol), prepared as described in Example l(C), and 2-(bromoacetyl)-pyridine hydrobromide (90 mg, 0.32 mmol) in dry N-methyl-2-pyrrolidinone (2.5 mL) was heated at 1000C for 5 h. The reaction mixture was cooled to room temperature, ethyl acetate was added and the organic layer was washed sequentially with water (twice) and with brine (twice). The organics were dried over sodium sulphate and evaporated under reduced pressure to afford a crude oil that was purified by flash chromatography: after 3 successive column chromatography purifications (silica gel, eluent: DCM/MeOH/NH4OH 98:2:0.2), 18 mg of (S)-(4-Fluoro-phenyl)(3-(4- (pyridin-2-yl)-oxazol-2-yl)-piperidin-l-yl)-methanone were obtained as a brown oil. Yield: 16%; LCMS (RT): 1.99 min (Method H); MS (ES+) gave m/z: 352.2 (MH+). 1H-NMR (DMSO-d6 353K), delta (ppm): 8.57 (ddd, IH) 8.43 (s, IH) 7.77-7.88 (m, 2H) 7.43-7.50 (m, 2H) 7.28-7.33 (m, IH) 7.19-7.27 (m, 2H) 4.21 (dd, IH) 3.78 (dd, IH) 3.46 (dd, IH) 3.13-3.35 (m, 2H) 2.15-2.28 (m, IH) 1.78-2.01 (m, 2H) 1.52-1.70 (m, IH).

With the rapid development of chemical substances, we look forward to future research findings about 17570-98-8.

Reference:
Patent; ADDEX PHARMA S.A.; WO2008/56259; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem