Tag: M.W:200-300

Related Products of 1241752-31-7 ,Some common heterocyclic compound, 1241752-31-7, molecular formula is C8H10BrNO2, 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. Preparation of Compound A mixture of 5-bromo-2,3-dimethoxypyridine (217 mg, 1.0 mmol), 3- cyanophenylboronic acid (220 mg, 1.5 mmol), Pd(PPh3)4 (173 mg, 0.15 mmol) and K2C03 (276 mg, 2.0 mmol) in 1 ,4- dioxane (5.0 ml) and H20 (1.5 ml) was degassed for 30 min. This mixture was heated to 100 C and stirred for 16 h. The reaction mixture was cooled to room temperature and partitioned between NaHC03 and EtOAc (3x), and washed with NaCl (lx). The organic phase was dried over Na2S04 and was concentrated. The resulting residue was purified by ISCO flash chromatography using 20% EtOAc in hexane to give 190 mg (79% yield) desired product as white solid. ‘H NMR (300 MHz, CDC13) delta: 7.91 (d, J – 2.1 Hz, 1H), 7.79- 7.73 (m, 2H), 7.61-7.53 (m, 2H), 7.17 (d, J = 2.1 Hz, 1H), 4.05 (s, 3H), 3.94 (s, 3H).

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. 1241752-31-7, 5-Bromo-2-ethoxy-3-methoxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; LAVOIE, Edmond J.; BAUMAN, Joseph David; PARHI, Ajit; SAGONG, Hye Yeon; PATEL, Disha; ARNOLD, Eddy; DAS, Kalyan; VIJAYAN, Suyambu Kesava; WO2014/43252; (2014); 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. 639091-75-1, name is Methyl 2-(Boc-amino)isonicotinate, the common compound, a new synthetic route is introduced below. Safety of Methyl 2-(Boc-amino)isonicotinate

Step 1. Preparation of methyl 2-[(tert-butoxycarbonyl(methyl)amino]isonicotinate A slurry of methyl 2-[(tert-butoxycarbonyl)amino]isonicotinate (5.0 g, 2.0E1 mmol) in DMF (75 mL) was cooled to ?0 C. (ice/NaCl) and treated with a 1.0 M solution of sodium hexamethyldisilazane in THF (24 mL, 24 mmol) dropwise over 25 min to afford a clear, yellow/brown solution. The reaction mixture was stirred for 30 min at 0 OC and treated with methyl iodide (1.4 mL, 22 mmol). The reaction mixture was stirred for 20 min, the cold bath was removed, and the reaction mixture stirred at rt for 2 h; HPLC/LC MS indicated complete conversion to product. The reaction mixture was cooled to ?0 C. and the reaction was quenched by the addition of saturated aqueous NH4Cl (25 mL). The mixture was allowed to warm to rt and was extracted with Et2O (3*50 mL). The combined organics were washed with saturated aqueous NaHCO3 (1*50 mL) and 10% aqueous LiCl (2*50 mL), dried (Na2SO4), and concentrated in vacuo to afford a bright yellow oil with precipitate. The crude material was further dried on high vacuum overnight to afford the crude title compound as a light colored solid/yellow oil (5.29 g). MS (ESI+) for C13H18N2O4LC m/z 267.1 (M+H)+; HPLC retention time: 3.78 min (Method B).

The synthetic route of 639091-75-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EXITHERA PHARMACEUTICALS INC.; Chrusciel, Robert A.; Gadwood, Robert C.; Hayward, Neil J.; Melnick, Michael J.; Navia, Manuel A.; Poel, Toni J.; Stassen, Frans L.; Stewart, Catherine A.; US2015/225389; (2015); 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.39774-26-0, name is 2-Bromo-6-phenylpyridine, molecular formula is C11H8BrN, molecular weight is 234.09, as common compound, the synthetic route is as follows.Application In Synthesis of 2-Bromo-6-phenylpyridine

To a solution of 21-1 (2.70 g, mixture from previous step) in tetrahydrofuran (50 mL) cooled to -78 C. under nitrogen, n-butyllithium (2.5 M in hexanes, 5.8 mL, 14.5 mmol) was added dropwise. The mixture was stirred for 45 minutes then N,N-dimethylformamide (1.80 mL, 23 mmol) was added. The mixture was stirred at -78 C. for 1 hour, warmed to room temperature, quenched with water, and extracted with ethyl acetate. The organic layer was washed three times with water, once with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography, eluting with 2.5% followed by 5% ethyl acetate in hexanes to give 6-phenylpicolinaldehyde (21-2, 1.24 g) as a yellow oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,39774-26-0, 2-Bromo-6-phenylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; Aviara Pharmaceuticals, Inc.; Biediger, Ronald J.; Benish, Michele A.; Hardy, Lindsay Bonner; Boyd, Vincent A.; Market, Robert V.; Thrash, Thomas P.; Young, Brandon M.; (83 pag.)US2018/312523; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1201676-03-0, 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one, 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, Application In Synthesis of 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one, blongs to pyridine-derivatives compound. Application In Synthesis of 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one

A mixture of 4,6-dichloro-2,3-dihydro-pyrrolo[3,4-c]pyridin-1-one (1.19 g, 5.87 mmol), triethylamine (2.97 g, 29.3 mmol), and crude trifluoroacetic acid salt of piperidine-4- carboxylic acid isobutyl amide [obtained by stirring 4-isobutylcarbamoyl-piperidine-1- carboxylic acid te/f-butyl ester (2.63 g, 8.80 mmol) in dichloromethane (20 mL) and trifluoroacetic acid (6 mL) for 1.5 hours, then removing solvents by rotary evaporation] in dioxane (10 mL) is heated in a 75 mL sealed tube at 120 0C for 68 h. Filtration of room temperature mixture does not lead to separation of regioisomers. The filtrate is concentrated down to dryness by rotary evaporation, dissolved into ethyl acetate, and then washed with water and brine. The organic layer is dried over sodium sulfate, filtered and concentrated down to dryness by rotary evaporation. This residue is then combined with solids from first filtration and eluted through a silica gel column (80:20 ethyl acetate / heptane, then 100% ethyl acetate, then 95:5 ethyl acetate / methanol). The more polar regioisomer (TLC solvents: 90:10 ethyl acetate / methanol) is concentrated down to dryness by rotary evaporation, then treated with a small amount of methanol. The pink solid is isolated by filtration (0.647 g, 1.84 mmol, 31 %). MS(ESI) m/z 351.20 (M+1 ). 1H NMR (400 MHz, DMSOd6) delta ppm 9.00 (s, 1 H), 7.79 (t, J=5.81 Hz, 1 H), 6.84 (s, 1 H), 4.54 (s, 2 H), 4.19 (d, J=13.39 Hz, 2 H), 3.09 – 2.92 (m, 2 H), 2.86 (dd, J=6.57, 6.06 Hz, 2 H), 2.48 – 2.36 (m, 1 H), 1.79 – 1.71 (m, 2 H), 1.71 – 1.52 (m, 3 H), 0.82 (d, J=6.82 Hz, 6 H).

The synthetic route of 1201676-03-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; WO2009/150230; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 179687-79-7, Adding some certain compound to certain chemical reactions, such as: 179687-79-7, name is 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine,molecular formula is C12H9ClN2O3, 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 179687-79-7.

Preparation of 3-chloro-4-(2-pyridylmethoxy)aniline from the nitrobenzene product of Example 1 was accomplished with catalytic hydrogenation using platinum on carbon. A typical hydrogenation was done using 6 volumes of THF, 2% by weight of 5% Pt/C (50% water wet), at 25 psi and at 25-30 C. for approximately 4-6 hours. The reaction is slightly exothermic and the temperature will rise to about 30-35 C. Cooling is necessary to maintain the temperature below 30 C. As a specific example, a mixture of 3-chloro-4-(2-pyridylmethoxy)nitrobenzene (0.15 kg, 0.57 mole) and 2% (w/w) of 5% Pt/C (6.0 g) in tetrahydrofuran (0.90 L) was hydrogenated at 25 psi for at least 5 hours. The mixture was filtered through a celite pad and washed with tetrahydrofuran (0.60 L). The filtrate was distilled to a volume of about 0.75 L and ethanol (1.12 L) was added. Distillation was continued to a volume of about 0.75 L and ethanol (2.85 L) was added. The mixture may be used ?as is? in the step of Example 3 below. ; Performing the hydrogenation in isopropyl alcohol (IPA), methanol (MeOH), or ethanol (EtOH) may result in the product being contaminated with late eluting impurity that partially precipitates out on standing in solution. It was found that performing the hydrogenation in a solvent where both the product and starting material are soluble, such as tetrahydrofuran (THF), resulted in greater product purity and required much less solvent. Thus, THF is a preferred solvent for this step. Experimental results showing the effect of different reaction conditions are shown in Table 2. For the larger scale runs, the first aniline intermediate was not isolated (?NI?) before proceeding with the next step. TABLE 2 Hydrogenation to Form First Aniline Intermediate 5% Scale (g) Pt/C** Solvent Vol Time (h) Yield (%) 2.0 1 IPA 50 3 79.6 18 2.0 5 EtOH 60 3100* 10 1 THF 10 4 94.5 7 10 1 EtOH 10 3 95.6 30 1.05 THF 6.5 12 96.3 14 100 2 THF 6 4.5 97.1 400 2 THF 6 4 NI 500 2 THF 6 4 NI 100 2 THF 6 5 NI 150 2 THF 6 5 NI 7 *Solid impurities noted after reaction completion. **percent by weight of starting material.

According to the analysis of related databases, 179687-79-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WYETH; US2006/270668; (2006); A1;,
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. 896722-51-3, name is 6-Methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine, the common compound, a new synthetic route is introduced below. HPLC of Formula: C14H12N2O2S

A solution of 50% NaOH (0.573 g) was added to N-protected 6-methyl-7-azaindole (0.390 g, 1.43 mmol) in Ethanol (10 mL). After refluxed for 8 h, the mixture was concentrated and was extracted with CHCl3. The organic layer was washed with water and dried. The solvent was evaporated in vacuo and the residue was purified on a silica gel column eluting with EtOAc/hexane (1:3) to give 6-methyl-1H-pyrrolo[2,3-b]pyridine (0.148 g, 78%).

The synthetic route of 896722-51-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hsieh, Hsing-Pang; Chao, Yu-Sheng; Liou, Jing-Ping; Chang, Jang-Yang; Tung, Yen-Shih; US2006/148801; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 946002-90-0, 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.946002-90-0, name is (S)-1-(5-Bromopyridin-2-yl)pyrrolidin-3-ol, molecular formula is C9H11BrN2O, molecular weight is 243.1, as common compound, the synthetic route is as follows.

(R)-5-Bromo-2-[3-(2,6-dichloro-4-methyl-phenoxy)-pyrrolidin-l-yl]-pyridine. ADDP (11.7 g, 45.4 mmol) was added to a sol. of compound Gl (8.82 g, 36.3 mmol) and 2,6-dichloro-/?-cresol (7.37 g, 40.0 mmol) in toluene (200 mL). The mixture was degassed with nitrogen for 5 min, and PBu3 (85%, 15.8 mL, 46.2 mmol) was added. The mixture was heated rapidly to 100 0C, and stirred at this temperature for 2 h. The mixture was allowed to cool to rt, and was diluted with heptane (200 mL). The mixture was filtered, and the filtrate was evaporated under reduced pressure. Purification of the residue by FC (EtO Ac/heptane 1 :7) yielded a crude title compound that was diluted with CH2Cl2. This mixture was washed with aq. IM NaOH. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Drying the residue under high vacuum yielded the pure title compound (13.5 g, 93%). LC-MS: tR = 0.92 min; ES+: 402.98.

The chemical industry reduces the impact on the environment during synthesis 946002-90-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2007/88514; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 89282-03-1 ,Some common heterocyclic compound, 89282-03-1, molecular formula is C5H4INO, 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.

Dry DMF (6.0 mL) was added to methyl 4-hydroxy-3-iodobenzoate (0.56 g, 2.0 mmol), ethynylboronic acid MIDA ester (0.47 g, 2.6 mmol), CuI (38 mg, 0.20mmol), PdCl2(Ph3P)2 (70 mg, 0.10 mmol) and Ph3P (52 mg, 0.20 mmol) under N2. 1,1,3,3-Tetramethylguanidine(TMG) (0.30 mL, 2.4 mmol) was added to the resulting solution under N2. The reactionmixture was stirred at 50 Cfor 22 h under N2. The resulting mixture was diluted with water to form aprecipitate, which was filtered, washed with water and dried at room temperature. The obtained solid was dissolved in acetone and purified by flash chromatography (SiO2, CH2Cl2 : MeOH = 10 : 1). The eluted material was washed with hot EtOH and dried to give 1A (493.6 mg, 75%) as a pale brown solid; Furo[3,2-c]-2-boronic acid (13): Prepared from 4-hydroxy-3-iodopyridine and ethynylboronic acidMIDA ester. The resulting mixture was diluted with water and extracted with AcOEt. The organic layers were dried over Na2SO4 and concentrated. The residue was purified by flash chromatography (SiO2,CH2Cl2 : MeOH = 10 : 1) to give 180.7 mg of 1 : 1 mixture of MIDA boronate and boronic acid as a pale yellow powder (41%). The mixture was treated with hot EtOH to afford 13 (109.9 mg, 34%) as a paleyellow solid; IR (cm-1) 3000, 1736, 1616, 1591, 1570, 1541, 1473, 1373, 1356, 1300, 1228, 1164, 1145,1039; 1H-NMR (DMSO-d6) delta 7.57 (d, J = 0.5 Hz, 1H), 7.65 (d, J = 6.0 Hz, 1H), 8.46 (d, J = 6.0 Hz, 1H),9.00 (s, 1H); HRMS calcd for C7H7NO3B [M+H] 164.0514, found 164.0513 (Delta 0.05).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89282-03-1, its application will become more common.

Reference:
Article; Sakurai, Yohji; Heterocycles; vol. 94; 7; (2017); p. 1322 – 1336;,
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.1163693-01-3, name is 2-Chloro-3-iodo-4-methoxypyridine, molecular formula is C6H5ClINO, molecular weight is 269.47, as common compound, the synthetic route is as follows.Recommanded Product: 2-Chloro-3-iodo-4-methoxypyridine

A solution of 4a3 (33.1 g, 123 mmol), F (7.14 g, 123 mmol) and Cul (23.39 g, 123 mmol) in NMP (165 mL) is heated at 80 C. Methyl-2-chloro-2,2-difluoroacetate (51.8 mL, 491 mmol) is added and the mixture is heated 1.5 h at 120 C. The reaction mixture is poured into brine and Et20 is added. The solid is filtered and the layers separated. The organic layer is washed with water and the aqueous layer is extracted with Et20. The combined organic layers are washed with brine, dried over Na2S04, filtered and concentrated in vacuum followed by Kugelrohr distillation to afford the trifluoromethyl derivative 4a4.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1163693-01-3, 2-Chloro-3-iodo-4-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; STAMMERS, Timothy; BARBEAU, Xavier; BEAULIEU, Pierre; BERTRAND-LAPERLE, Megan; BROCHU, Christian; EDWARDS, Paul, J.; FORGIONE, Pasquale; GODBOUT, Cedrickx; HUCKE, Oliver; JOLY, Marc-Andre; LANDRY, Serge; LEPAGE, Olivier; NAUD, Julie; PESANT, Marc; POIRIER, Martin; POIRIER, Maude; THAVONEKHAM, Bounkham; WO2011/32277; (2011); A1;,
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. 69045-83-6, name is 2,3-Dichloro-5-(trichloromethyl)pyridine, the common compound, a new synthetic route is introduced below. Application In Synthesis of 2,3-Dichloro-5-(trichloromethyl)pyridine

EXAMPLE 10 2,3-Dichloro-5-(trifluoromethyl)pyridine STR12 A 360 milliliter (ml) TEFLON PFA reaction flask, fitted with a PFA reflux condenser, an HF bleed tube, a magnetic stirrer and an optical pyrometer, was charged with 180 grams (g) of 2,3-dichloro-5-(trichloromethyl)pyridine and 4.3 g (5 mole percent) of FeCl2. Anhydrous HF gas was introduced into the reaction mixture (~4 g/hr) below the surface of the liquid as the reaction mixture was heated to a temperature between 170 C. and 175 C. This temperature (170-175 C.) was maintained for a period of 70 hours with constant agitation. Standard gas-liquid chromatography (GLC) analysis of the product indicated that the reaction product contained:

The synthetic route of 69045-83-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Dow Chemical Company; US4590279; (1986); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem