Tag: M.W:200-300

Synthetic Route of 116986-09-5, Adding some certain compound to certain chemical reactions, such as: 116986-09-5, name is Methyl 3-(bromomethyl)picolinate,molecular formula is C8H8BrNO2, 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 116986-09-5.

To a solution of S-[(6-chloro-4-methyl-3-pyridyl) methyl] ethanethioate (1.67 g, 7.8 mmol) in 50 mL methanol was added K2CO3 (2.14 g, 15.5 mmol). The mixture was stirred for 30 min at room temperature. Then methyl-(3-bromomethyl)pyridine-2-carboxylate (1 .78 g, 7.8 mmol) was added and it was stirred for 2.5 hours at room temperature. The mixture was concentrated to give the crude product (2.87 g, crude, MS+1 =322).

According to the analysis of related databases, 116986-09-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BASF SE; BASF SCHWEIZ AG; WITSCHEL, Matthias; KRAUS, Helmut; HUTZLER, Johannes; NEWTON, Trevor William; REINGRUBER, Ruediger; FRASSETTO, Timo; PARRA RAPADO, Liliana; BESONG, Gilbert; RACK, Michael; KLOET, Andree van der; SEITZ, Thomas; LERCHL, Jens; KREUZ, Klaus; PASTERNAK, Maciej; EVANS, Richard Roger; WO2013/178585; (2013); A1;,
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Electric Literature of 69422-72-6, Adding some certain compound to certain chemical reactions, such as: 69422-72-6, name is 2,4,6-Trichloronicotinic acid,molecular formula is C6H2Cl3NO2, 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 69422-72-6.

A solution of the product of EXAMPLE 1 1C (1.5 g,6.7 mmol) in dichloromethane (50 mL) was treated at room temperature with 2 drops ofN,N-dimethylformamide. Oxalyl chloride (1.27 g, 10 mmol) was added dropwise over 15 minutes and stirring was continued for 2 hours. The solution was concentrated and dried under vacuum to give the crude acid chloride. Ammonium (gas) was passed through a solution of the acid chloride in tetrahydrofuran (20 mL) and the mixture stirred at room temperature for 0.5 hours. The mixture was concentrated under vacuum and the residue purified by flash chromatography on silica gel (200-3 00 mesh) eluting with 100/1 dichloromethane/methanol to give the title compound. MS: 225 (M+H).

According to the analysis of related databases, 69422-72-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBVIE INC.; Vasudevan, Anil; Penning, Thomas Dale; Chen, Huanming; Liang, Bo; Wang, Shaohui; Zhao, Zhongqiang; Chai, Dikun; Yang, Leifu; Gao, Yingxiang; Pliushchev, Marina; US2014/171429; (2014); A1;,
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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. 190271-88-6, name is Methyl 2-chloro-5-nitronicotinate, molecular formula is C7H5ClN2O4, 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. Recommanded Product: Methyl 2-chloro-5-nitronicotinate

2-Chloro-5-nitro-nicotinic acid methyl ester (578 mg, 2.44 mmol) and n-propyl hydrazine oxalate (400 mg, 2.44 mmol) in DMF (10 ml) was treated with K2CO3 (672 mg, 4.87 mmol). The mixture was stirred at 80 C. for 3 hr and then at RT overnight. The reaction mixture was then concentrated and diluted with EtOAc. The organic layer was partitioned over water and solid citric acid was added to acidify the mixture to pH 1. The organic layer was washed with brine, dried over Na2SO4 and concentrated to dryness. The solid obtained was triturated with CH2Cl2 and then hexanes to afford the product, 5-nitro-1-propyl-1,2-dihydro-pyrazolo[3,4-b]pyridin-3-one (405 mg, Yield: 75%). LCMS calcd for C9H10N4O3 (m/e) 222, obsd. 223 (M+H).

With the rapid development of chemical substances, we look forward to future research findings about 190271-88-6.

Reference:
Patent; Bolin, David Robert; Cai, Jianping; Cheung, Adrian Wai-Hing; Goodnow, JR., Robert Alan; Hamilton, Matthew Michael; Li, Shiming; McDermott, Lee Apostle; Yun, Weiya; US2009/76275; (2009); A1;,
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Electric Literature of 1018505-59-3, 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 1018505-59-3 as follows.

To a solution of 3-chloro-7-(2, 6-dichloro-3, 5-dimethoxyphenyl) isoqinoline (600 mg, 1.628 mmol), 5-(4-ethylpiprazine-l-yl) pyridine-2-amine (step 3.1) (376 mg, 1.82 mmol), X-Phos (77.60 mg, 10 mol %) and cesium carbonate (1.06 g, 1.25 mmol) in Toluene (15 mL) and t- BuOH (5 mL) (4: 1) argon was purged for 20 min. Then was added Pd2 (dba)3 (149 mg, 10 mol %) again argon was purged for 5 min. The reaction mixture was heated at 120C overnight. The reaction mixture was cooled to room temperature and filtered through celite pad and filtrate was concentrated under reduced pressure. Product was purified by column chromatography on silica gel column using DCM: MeOH: NH3 aq. (95:5: 1%) as an eluent to afford 7-(2, 6-dichloro-3, 5-dimethoxyphenyl)-N-[5-(4-ethylpiperazin-l-yl) pyridin-2-yl] isoquinoline-3 -amine (600 mg) as a pale yellow solid. 1H NMR (400 MHz, CDC13) delta 8.97 (s, 1H), 8.09 (dd, J = 25.7, 7.3 Hz, 2H), 7.82 – 7.68 (m, 2H), 7.41 (dd, J = 8.5, 1.6 Hz, 1H), 7.32 (dd, J = 8.9, 2.9 Hz, 1H), 7.17 – 7.10 (m, 1H), 6.65 (s, 1H), 3.99(s, 6H), 3.26 – 3.16 (m, 4H), 2.71 – 2.62 (m, 4H), 2.51 (q, J = 7.2 Hz, 2H), 1.15 (t, J= 7.2 Hz, 3H). M/Z: 537.1, M+l : 538.6, tR= 0.81 min. (System 1)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1018505-59-3, its application will become more common.

Reference:
Patent; EVOTEC (UK) LTD.; MC CARTHY, Clive; MILLS, Matthew; WO2014/44846; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 112193-41-6, 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. 112193-41-6, name is 5-Bromonicotinohydrazide, molecular formula is C6H6BrN3O, 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.

EXAMPLE 102 4-[1-(3-Aminopropyl)-5-fluoro-indol-3-yl]-5-(5-bromo-pyridin-3-yl)-2,4-dihydro-[1,2,4]triazol-3-one hydrochloride The title compound was prepared by the method described in Example 45 starting from the product of Example 45d) and 5-bromo-nicotinic acid hydrazide. 1H NMR (400 MHz, DMSO-d6): delta12.45 (1H, s); 8.68 (1H, d); 8.48 (1H, d); 8.00 (1H, m); 7.89 (3H, bs); 7.80 (1H, s); 7.70 (1H, m); 7.16 to 7.09 (2H, m); 4.35 (2H, m); 2.75 (2H, m); 2.04 (2H, m). APCI-MS m/z: 431 [MH+].

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 112193-41-6, 5-Bromonicotinohydrazide.

Reference:
Patent; Astrazeneca AB; US6492406; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1034467-27-0, 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.1034467-27-0, name is 2-Fluoro-4-iodo-5-(methoxymethoxy)pyridine, molecular formula is C7H7FINO2, molecular weight is 283.04, as common compound, the synthetic route is as follows.

Preparation 476-Fluoro-4-iodo-pyridin-3 -olAdd HCl (3 M in water, 31 mL, 93.0 mmol) to a solution of 2-fluoro-4-iodo-5- methoxymethoxy-pyridine (3.9 g, 13.8 mmol) in THF (20 mL). Stir the mixture at 60 0C for 3 h and cool down the mixture. Adjust the pH to 7 with slow addition of a saturated aqueous sodium bicarbonate solution. Extract the solution with ethyl acetate three times. Wash the organic layer with aqueous saturated sodium chloride. Dry the mixture over sodium sulfate. Concentrate the solution in vacuo to afford the title compound (3.2 g, 97 %) as a yellow solid. MS (ES) m/z 240 [M+ 1]+.

The chemical industry reduces the impact on the environment during synthesis 1034467-27-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ELI LILLY AND COMPANY; WO2008/144222; (2008); A2;,
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Pyridine | C5H5N – PubChem

Related Products of 380380-64-3, 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.380380-64-3, name is 5-Bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine, molecular formula is C7H6BrN5, molecular weight is 240.06, as common compound, the synthetic route is as follows.

Under nitrogen protection, to 35.3L of tetrahydrofuran was added 3-fluoro-4-bromophenylcarbamic acid benzyl ester 4.7Kg (14.5mol), stirred at 20 ~ 30 and added zinc powder 3.8Kg (58.1mol), 27.4 g (0.145 mol) of cobaltocene, stirred at 20 C. to 30 C. for 4 hours to 5 hours, filtered, and washed with 11.7 L of tetrahydrofuran to obtain a solution stored under nitrogen, which is a solution of terdazolamide intermediate III.The solution of teridazole amine phosphate intermediate III was stirred at 20 C to 30 C, and 2-methyl-5- (5-bromopyridin-2-yl) tetrazole 3.83Kg (15.95mol) and sodium carbonate 3.1Kg were added (29.2mol), tris (dibenzylideneacetone) dipalladium 26.5g (0.029mol), heated to 65 C to 70 C and stirred for 5 hours to 6 hours.After cooling, filter through 2.5Kg of diatomaceous earth, add 10L of tetrahydrofuran and 15% saline in mass concentration to the mother liquor (the mass concentration refers to the mass of sodium chloride as a percentage of the total mass of saline). After 4L, organic Separate the phases to dry, concentrate in vacuum (temperature 35 C- 55 C , pressure -0.08MPa -0.1MPa) to dryness, draw 30L of ethyl acetate, heat to 70 C- 75 C and stir for 0.5 hours to 1 hour, cool to Stir at 0 to 10 C for 1 to 2 hours, centrifuge, rinse three times with 3L of ethyl acetate, vacuum dry (vacuum degree -0.01MPa to -0.1MPa, temperature 45 C to 55 C) for 16 hours to obtain an off-white solid Tedizolid phosphate intermediate II 4.36kg, total yield 74.4%. HPLC purity 98.74%.

Statistics shows that 380380-64-3 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine.

Reference:
Patent; Shanghai Bozhi Yan Xin Pharmaceutical Co., Ltd.; Chen Jian; Liu Zhenfeng; Ying Shuhuan; (16 pag.)CN110804038; (2020); A;,
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. 75073-11-9, name is 5-Iodo-6-methylpyridin-2-amine, molecular formula is C6H7IN2, 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. Formula: C6H7IN2

EXAMPLE 255: 6-methyl-5- -(trifluoromethyl)-lH-indazol-4-yl)pyridin-2-amine [0802] To a mixture of 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)- lH-indazole (0.05 g, 0.160 mmol), 5-iodo-6-methylpyridin-2-amine (0.025 g, 0.107 mmol) and PdCl2(dppf) (0.012 g, 0.016 mmol) in dioxane (1.5 mL) was added 2N sodium carbonate (0.160 mL, 0.320 mmol). The reaction mixture was heated in a microwave reactor at 130C for 50 minutes. LCMS showed incomplete conversion of the starting material, so the reaction mixture was heated at 130C for an additional 50 minutes. LCMS again showed incomplete conversion. More catalyst was added, and the reaction mixture was again heated at 130C for 50 minutes. The reaction mixture was subsequently filtered through a micro filtration frit, which was rinsed with methanol. The solvents were removed in vacuo. The residue was taken up in DMSO and methanol (1 : 1) and was purified by preparative HPLC, eluting with 25% ACN (containing 0.035% TFA) in H20 (containing 0.05% TFA). The product-containing fractions were dried under vacuum to give a TFA salt of the title compound as a tan film (12 mg, 26%). 1H NMR (400 MHz, DMSO-d6) delta ppm 2.32 (s, 3 H), 6.94 (d, J=9.35 Hz, 1 H), 7.37 (s, 1 H), 7.97 (d, J=8.84 Hz, 1 H), 8.02 (s, 1 H), 8.14 (s, 1 H); ESI-MS m/z [M+H]+ calc’d for Ci4HnF3N4, 293.1; found 293.2

With the rapid development of chemical substances, we look forward to future research findings about 75073-11-9.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; CHERUVALLATH, Zacharia; ERICKSON, Philip; FENG, Jun; KOMANDLA, Mallareddy; LAWSON, John David; MCBRIDE, Christopher; MIURA, Joanne; MURPHY, Sean; TANG, Mingnam; TON-NU, Huong-Thu; WO2013/130855; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 849068-61-7 ,Some common heterocyclic compound, 849068-61-7, molecular formula is C8H5BrN2O2, 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 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.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,849068-61-7, its application will become more common.

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

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. 195044-14-5, name is 2-Bromo-6-tert-butylpyridine, molecular formula is C9H12BrN, 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. Product Details of 195044-14-5

Step-1: Synthesis of 1-(6-(tert-butyl)pyridin-2-yl)-2-cyclopropyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one To a stirred solution of 2-cyclopropyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one (500 mg, 2.242 mmol, 1.0 eq) and 2-bromo-6-(tert-butyl)pyridine (586 mg, 2.690 mmol, 1.20 eq) in (12 mL) of dioxane was added potassium carbonate (619 mg, 4.484 mmol, 2.0 eq) and the resulting mixture was purged with nitrogen for 10 min followed by addition of copper iodide (85 mg, 0.448 mmol, 0.2 eq), and N,N’-dimethylethylenediamine (DMEDA) (80 mg, 0.896 mmol, 0.4 eq) and again purged with nitrogen for 10 min, stirred at 90 C. for overnight. After completion of reaction, the reaction mixture was diluted with water and extracted with EtOAc (50 mL*2). The combined organic layer was washed with water (50 mL), brine solution (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude product, which was purified by flash chromatography [silica gel 100-200 mesh; elution 0-30% EtOAc in hexane] to afford the desired product, 1-(6-(tert-butyl)pyridin-2-yl)-2-cyclopropyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one (300 mg, 37.51%) as light yellow viscous.

With the rapid development of chemical substances, we look forward to future research findings about 195044-14-5.

Reference:
Patent; giraFpharma LLC; Chakravarty, Sarvajit; PHAM, Son Minh; Kankanala, Jayakanth; AGARWAL, Anil Kumar; PUJALA, Brahmam; SONI, Sanjeev; ARYA, Satish K.; PALVE, Deepak; Gupta, Ashu; KUMAR, Varun; (498 pag.)US2019/106427; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem