Tag: M.W:200-300

Adding a certain compound to certain chemical reactions, such as: 1227048-78-3, Methyl 2-amino-5-iodonicotinate, 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, 1227048-78-3, blongs to pyridine-derivatives compound. Application In Synthesis of Methyl 2-amino-5-iodonicotinate

Preparation 76: 2-Amino-5-(4-fluorophenoxy)nicotinic add methyl ester To 2-aminonicotimc acid methyl eater (5.5g, 36.2mmol) in DMF (70mL) was added N-iodosuccinimide (9.8g, 43.7rmnol). After 16h the mixture was poured into sat. sodium thiosulfite solution and then extracted with Et20. The organic phase was washed with water, brine, dried (MgS04) and the solvent was removed in vacuo to give 2-amino-5-iodonicotinic acid methyl ester. To 4-fluorophenol (2.4g, 21.6mmol) in dioxane (50mL) was addedCS2CO3 (6g, 25.2mmol) and the mixture was heated to 50C. After 20min Cul (0.56g, 3.0mmol) and 2-ammo-5-iodonicotrriic acid methyl ester (2g, 7.2mmol) were added and the mixture heated under reflux for 16h. After cooling the solvent removed in vacuo, the residue was partitioned between EtOAc and 4N HQ, the organic phase was extracted with 6N HC1 and the organic phase discarded. The combined aqueous phase was basified with NH4OH and re-extracted with EtOAc. The organic phase was dried (MgS04) and the solvent was removed in vacuo. The residue was purified by column chromatography (1 :3EtOAcrHexane) to give, after removal of the solvent in vacuo, the title compound: RT= 3.30min; m/z (ES+) = 263.2 [M+ Iff”.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1227048-78-3, its application will become more common.

Reference:
Patent; PROSIDION LIMITED; BLOXHAM, Jason; BRADLEY, Stuart Edward; SAMBROOK-SMITH, Colin Peter; SMYTH, Donald; KEILY, John; DAWSON, Graham John; RASAMISON, Chrystelle Marie; BELL, James Charles; WO2011/117254; (2011); A1;,
Pyridine – Wikipedia,
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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. 1111637-74-1, name is 1-(5-Bromo-2-fluoropyridin-3-yl)ethanone, the common compound, a new synthetic route is introduced below. Product Details of 1111637-74-1

Step 2: 5-bromo-3-methyl-lH-pyrazolo[3,4-b]pyridine To a solution of l-(5-bromo-2-fluoropyridin-3-yl)ethanone (43 g, 197.2 mmol) in ethanol (500 niL) was added hydrazine monohydrate (34.8 g, 591.6 mmol, 85 %) at RT. After addition, the reaction mixture was refluxed overnight. The reaction mixture was cooled to RT and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 5% to 17% ethyl acetate in petroleum ether) affording 5-bromo-3-methyl-lH-pyrazolo[3,4-b]pyridine (35g, 83.7%): NMR (400 MHz, DMSO-d6): delta 13.42 (s, 1H), 8.51 (m, 2H), 2.54 (s, 3H).

The synthetic route of 1111637-74-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; HUESTIS, Malcolm; KELLAR, Terry; PATEL, Snahel; SHORE, Daniel; SIU, Michael; (260 pag.)WO2016/142310; (2016); A1;,
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Related Products of 1111637-94-5 ,Some common heterocyclic compound, 1111637-94-5, molecular formula is C8H7BrN2, 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 solution of 5-bromo-3-methyl-1H-pyrrolo [2, 3-b] pyridine (1.50 g, 7.11 mmol) in 5 mL of DCM were added DMAP (0.080 g, 0.71 mmol) and di-tert-butyl dicarbonate (1.55 g, 7.11 mmol) . The resulting solution was stirred for 1 h at room temperature and then concentrated under reduced pressure to afford tert-butyl 5-bromo-3-methyl-1H-pyrrolo [2, 3-b] pyridine-1-carboxylate as a white solid which was used in the subsequent step without further purification. MS (EI) calc?d for C13H16BrN2O2[M+H]+, 311 found, 311.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1111637-94-5, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ACHAB, Abdelghani Abe; CHRISTOPHER, Matthew P.; FRADERA LLINAS, Francesc Xavier; KATZ, Jason D.; METHOT, Joey L.; ZHOU, Hua; XU, Shimin; FU, Jianmin; FU, Ning; LI, Yabin; WANG, Xichao; (228 pag.)WO2017/166104; (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. 116355-18-1, name is 6-Bromo-7-methylimidazo[1,2-a]pyridine, molecular formula is C8H7BrN2, 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. Application In Synthesis of 6-Bromo-7-methylimidazo[1,2-a]pyridine

(2) 6-bromo-3-iodo-7-methylimidazo[l,2-a]pyridine.; To a 15O mL round bottomed flask was added 6-bromo-7-methylimidazo[l,2-a]pyridine (4.300 g, 20.37 mmol), sodium acetate anhydrous (2.95 mL, 55.0 mmol) and MeOH (60 mL). The resulting mixture was cooled to 0 0C followed by adding iodine (5.7 g, 22.41 mmol). After the addition, ice bath was removed. After 20 h, the solid in the reaction mixture was collected by filtration. The solid was washed with MeOH affording the desired product as a light grey solid (5.1 g). MS (ESI pos. ion) m/z: 336.7. Calcd exact mass for C8H6BrIN2: 335.9. 1H NMR (300 MHz, CHLOROFORM-J) delta ppm 2.50 (s, 3 H) 7.49 (s, 1 H) 7.64 (s, 1 H) 8.30 (s, 1 H).

With the rapid development of chemical substances, we look forward to future research findings about 116355-18-1.

Reference:
Patent; AMGEN INC.; BO, Yunxin, Y.; LIU, Longbin; NISHIMURA, Nobuko; NORMAN, Mark, H.; SIEGMUND, Aaron, C.; TAMAYO, Nuria, A.; YANG, Kevin; WO2010/108074; (2010); A2;,
Pyridine – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 75291-85-9, 5-Bromo-2-chloronicotinamide, 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, 75291-85-9, blongs to pyridine-derivatives compound. SDS of cas: 75291-85-9

Preparation 133(35,45)-4-[(5-bromo-3-carbamoylpyridin-2-yl)oxyl-3-fluoropiperidine- 1 -carboxylate To a solution of tert-butyl (3S,4S)-3-fluoro-4-hydroxypiperidine- 1 -carboxylate (WO 20131011402 Al, 605 mg, 2.76 mmol) in DMSO (4 mL) was added potassium tert-butoxide (464 mg, 4.14 mmol) and the mixture stirred at room temperature for 30 minutes. 5-bromo-2- chloronicotinamide (Preparation 177, 650 mg, 2.76 mmol) was added and the reaction stirred at room temperature for 16 hours. The reaction was quenched by the addition of water andextracted into EtOAc. The organic layer was collected, washed with water, dried over sodiumsulphate and concentrated in vacuo. The residue was purified using silica gel columnchromatography eluting with 30% EtOAc in heptanes to afford the title compound (800 mg,69%).1H NMR (400 MHz, DMSO-d6): O ppm 1.41 (5, 9H), 1.74 (m, 1H), 2.06 (m, 1H), 3.28-3.83 (m,4H), 4.80-4.93 (m, 1H), 5.41 (m, 1H), 7.64 (br 5, 1H), 7.68-7.82 (m, 2H), 8.21 (m, 1H), 8.42 (5,1H).MS mlz 318 [M79Br-Boc+H]

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,75291-85-9, its application will become more common.

Reference:
Patent; PFIZER LIMITED; SKERRATT, Sarah Elizabeth; BAGAL, Sharanjeet Kaur; SWAIN, Nigel Alan; OMOTO, Kiyoyuki; ANDREWS, Mark David; WO2015/92610; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 13626-17-0, 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 13626-17-0 as follows.

Intermediate 24: 2-(benzeuesulfonyl)-2-(5-bromo-4-chloropyridin-3-yl)acetonitrile To a stirred and nitrogen degassed solution of 2-{benzenesulfonyflacetonitrile (CM 7605-25-9; 7.64 g, 42.20 mmol) in anhydrous DME (100 mL) was added sodium hydride (3.83 g, 96 mmol, 6o% dispersion in oil) at o C. The mixture was stirred at oC for 5 mm and then at it for 15 mm. This mixture was added to a previously nitrogen degassed solution of 3,5-dibromo-4-chloropyfldane (CM 13626-17-0; 10.40 g, 38.30 mmol), tetrakis(triphenylphosphane) palladium (i.ii g, 958 jimol) in anhydrous DME (100 mL). The reaction mixture was heated at reflux for 16 h. The reaction mixture was partitioned between EtOAc and water. The organic phase was washed with brine, dried (MgSO4) and concentrated in vacuo. The crude product was purified by column chromatography (Ci8-silica, o-8o% acetonitrile / water (with o.i% ammonia)) to affordthe title compound. -?H NMR (400 MHz, DMSO-d6) 6 ppm 7.37 7.58 (m, 3 H) 7.67 – 7.83 (m, 3 H) 8.13 – 8.29 (m, 1 H) 8.31 – 8.44 (m, 1 H)MS ES: 372

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13626-17-0, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; TAKEDA CAMBRIDGE LTD; BARKER, Gregory; DAVENPORT, Richard; DOWNHAM, Robert; FARNABY, William; GOLDBY, Anne; HANNAH, Duncan; HARRISON, David; WILLEMS, Henriette; (390 pag.)WO2015/198045; (2015); A1;,
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Pyridine | C5H5N – PubChem

Related Products of 1352625-30-9, 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.1352625-30-9, name is 3-Bromo-6-fluoropyrazolo[1,5-a]pyridine, molecular formula is C7H4BrFN2, molecular weight is 215.02, as common compound, the synthetic route is as follows.

c) 6-Fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[1,5-a]pyridine A mixture of 3-bromo-6-fluoropyrazolo[1,5-a]pyridine (Preparation 103b, 0.300 g, 1.4 mmol), potassium acetate (0.492 g, 5.0 mmol) and bis(pinacolato)diboron (2.77 g, 10.9 mmol) in 1,4-dioxane (5 mL) contained in a Schlenck vessel was submitted to three vacuum-argon cycles and tetrakis(triphenylphosphine)palladium(0) (0.380 g, 0.33 mmol) was then added. The mixture was further submitted to three vacuum-argon cycles, sealed and then was stirred and heated to 100 C. After 20 hours, the reaction mixture was cooled, evaporated and then taken up in pentane and filtered through diatomaceous earth (Celite) and the filter cake was washed with a mixture of ethyl acetate/ether (3:2). The combined filtrate and washings were evaporated and the residue was purified by reverse phase chromatography (C-18 silica from Waters, water/acetonitrile/methanol as eluents [0.1% v/v formic acid buffered] 0% to 100%) to give the title compound (0.130 g, 36%) as a yellow solid. LRMS (m/z): 263 (M+1)+.1H NMR (300 MHz, CDCl3) delta ppm (two sets of peaks are seen in the NMR due to the presence of both the boronate and boronic acid): NMR of boronate: 1.21 (s, 12H), 7.56 (m, 1H), 8.02 (m, 1H), 8.36 (s, 1H), 9.16 (m, 1H).; PREPARATION 104 2-(6-Fluoropyrazolo[1,5-a]pyridin-3-yl)-9-(tetrahydro-2H-pyran-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-purin-8(9H)-one [Show Image] A mixture of 2-chloro-9-(tetrahydro-2H-pyran-4-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7,9-dihydro-8H-purin-8-one (Preparation 3, 0.150 g, 0.39 mmol), 6-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[1,5-a]pyridine (Preparation 103, 0.183 g, 0.70 mmol) and potassium acetate (0.134 g, 1.37 mmol) in 1,4-dioxane (5 mL) and water (1.5 mL) contained in a Schlenck vessel was submitted to three vacuum-argon cycles and tetrakis(triphenylphosphine)palladium(0) (0.040 g, 0.03 mmol) was then added. The mixture was further submitted to three vacuum-argon cycles, sealed and then was stirred and heated under microwave irradiation (“Initiator sixty” from Biotage) at 120 C under an atmosphere of argon. After 40 minutes, further 2-chloro-9-(tetrahydro-2H-pyran-4-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7,9-dihydro-8H-purin-8-one (0.060 g, 0.16 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.020 g, 0.017 mmol) were added and heating was continued for 90 minutes. The reaction mixture was evaporated and then was partitioned between ethyl acetate and water and the organic layer was dried (MgSO4) and concentrated. The residue was purified by flash chromatography (3:1 to 2:1 hexanes/ethyl acetate) to give the title compound (0.096 g, 50%) as pale yellow solid. LRMS (m/z): 485 (M+1)+.1H NMR (300 MHz, CDCl3) delta ppm 0.06 (s, 9H), 1.00 (t, 2H), 1.80 (m, 2H), 2.91 (dq, 2H), 3.49 (s, 2H), 3.68 (m, 2H), 4.22 (m, 2H), 4.63 (m, 1H), 5.25 (s, 2H), 7.38 (t, 1H), 8.40 (s, 1H), 8.52 (m, 1H), 8.65 (dd, 1H), 8.78 (s, 1H).

Statistics shows that 1352625-30-9 is playing an increasingly important role. we look forward to future research findings about 3-Bromo-6-fluoropyrazolo[1,5-a]pyridine.

Reference:
Patent; Almirall, S.A.; EP2397482; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 109306-86-7 ,Some common heterocyclic compound, 109306-86-7, molecular formula is C11H8BrN, 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 solution of 117.5 mg of 2- (2-bromophenyl) pyridine (0.5 mmol)And 70.15 mg of potassium methoxide (1 mmol) were dissolved in 1 mL of deuterated acetonitrile, and 200 muL of hexamethyldisilane (1 mmol) was added dropwise to the mixture, and the mixture was stirred at room temperature for 12 h. After completion of the reaction, 10 mL of water was quenched and extracted with 30 mL of ether three times. The organic phase was collected and the solvent was removed under reduced pressure. The eluent was petroleum ether: ethyl acetate = 10: 1 (v / v) to give 68 mg of 2- (2-deuterated) pyridine (pale yellow liquid in 87% yield).

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. 109306-86-7, 2-(2-Bromophenyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Wuhan University; Liu Wenbo; Wang Xin; Zhong Dayou; (23 pag.)CN106928117; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 866775-18-0, 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. 866775-18-0, name is Methyl 3-amino-6-bromo-5-(trifluoromethyl)picolinate, molecular formula is C8H6BrF3N2O2, 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 : Methyl 3-amino-6-(4-fluorophenyl)-5-(trifluoromethyl)picolinate 3-Amino-6-bromo-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester (Intermediate 3D) (200 mg, 0.669 mmol), 4-fluorophenylboronic acid (94 mg, 0.669 mmol) and 1 , 1 ‘bis(diphenylphosphoshio)ferrocene palladium dichloride (Apollo) were suspended in THF (2 ml) and 1 M Cs2C03 (0.667 ml). The vial was flushed with N2, sealed and heated at 160C for 15 minutes using microwave radiation. The reaction mixture was partitioned between EtOAc (50 ml) and water (50 ml). The organic portion was separated and washed with brine (30 ml), dried over MgS04, filtered and concentrated in vacuo. Purification by chromatography on silica eluting with 0-80% EtOAc in iso-hexane afforded the title compound; LCMS: Rt = 1 .47 mins, [M+H]+ 315.1 ; Method 2minl_C_v002. Step 2: 3-Amino-6-(4-fluorophenyl)-5-(trifluoromethyl)picolinic acid To a stirred solution of methyl 3-amino-6-(4-fluorophenyl)-5-(trifluoromethyl)picolinate (step 1 ) (6.00 mmol) in EtOH (5 ml) was added 2M NaOH (3 ml, 6.00 mmol) and the solution was stirred at RT for 15 minutes. The resulting mixture was diluted with water (10 ml) and the pH was adjusted to pH 6 using 1 M HCI. The mixture was extracted with DCM (2 x 10 ml) and the phases were separated using a phase separating cartridge. The combined organic extracts were concentrated in vacuo and used in the next step without further purification; LCMS: Rt = 1 .42 mins, [M+H]+ 301.1 ; Method 2minl_C_v002. Step 3: 3-Amino-6-(4-fluorophenyl)-N-(1 H-pyrazol-3-yl)-5- (trifluoromethyl)picolinamide A stirred solution of 3-amino-6-(4-fluorophenyl)-5-(trifluoromethyl)picolinic acid (0.167 mmol) in dry NMP (2 ml) was treated with 1 H-pyrazol-3-amine (0.183 mmol). After stirring at RT, triethylamine (0.366 mmol) was added and stirring continued for 5 minutes. HATU (0.183 mmol) was added and the resulting mixture was sealed and heated at 100 C for 1 hour using microwave radiation. The mixture was partitioned between EtOAc (25 ml) and 1 M NaOH (25 ml). The organic portion was separated, washed with water (25 ml), dried over MgS04 and concentrated in vacuo. Purification by mass directed LCMS eluting with TFA/MeCN/water afforded the title compound as a TFA salt. The salt was partitioned between EtOAc (10 ml) and sodium bicarbonate (10 ml). The organic portion was separated, passed through phase separating cartridge and concentrated in vacuo to afford the title compound; LCMS: Rt = 1 .58 mins, [M+H]+ 366.2; Method 2minLC_v002. 1 H NMR (400MHz, DMSO – d6) delta 12.6 (1 H, s), 10.2 (1 H, s), 7.82 (1 H, s), 7.78 (1 H, s), 7.62 (2H, m), 7.3 – 7.4 (4H, m), 6.72 (1 H, s).

According to the analysis of related databases, 866775-18-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; BALA, Kamlesh, Jagdis; BUDD, Emma; EDWARDS, Lee; HOWSHAM, Catherine; LEGRAND, Darren, Mark; TAYLOR, Roger, John; WO2013/38390; (2013); A1;,
Pyridine – Wikipedia,
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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. 166266-19-9, name is 5-Iodo-3-methylpyridin-2-amine. A new synthetic method of this compound is introduced below., COA of Formula: C6H7IN2

Step 23.1: 5-iodo-3-methylpyridin-2-ol Sodium nitrite (0.708 g, 10.25 mmol) was added to a mixture of 5-iodo-3-methyl-pyridin-2-ylamine (2 g, 8.55 mmol) and H2SO4 (12 mL) at 0 C. The reaction mixture was stirred 15 min at 60 C., allowed to cool down, and poured onto crushed ice. Boric acid (1.057 g, 17.09 mmol) was added and the solution was quickly heated to 100 C. The reaction mixture was cooled down and neutralized with a saturated aq. NH4OH solution. The suspension was filtered to afford the crude title product (1.67 g, 7.11 mmol, 83% yield) as a brown solid. tR: 2.85 min (HPLC 1); tR: 0.62 min (LC-MS 2); ESI-MS: 236 [M+H]+ (LC-MS 2).

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, 166266-19-9, 5-Iodo-3-methylpyridin-2-amine.

Reference:
Patent; NOVARTIS AG; BLANK, Jutta; BORDAS, Vincent; COTESTA, Simona; GUAGNANO, Vito; RUEEGER, Heinrich; VAUPEL, Andrea; US2014/349990; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem