Tag: M.W=200-300

Reference of 887267-47-2, 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 887267-47-2 as follows.

General procedure: Triphosgene (0.09 g, 0.3 mmol) was dissolved in anhydrous CH2Cl2 (15 mL) and the mixture was stirred on the ice-bath for 15 min. 3-Bromo-5-(trifluoromethyl)aniline (0.16 g, 0.7 mmol) in anhydrous CH2Cl2 (10 mL) was added dropwise to the above mixture and stirring continued for 20 min. Et3N (0.12 mL, 0.89 mmol) diluted with CH2Cl2 (5 mL) was then added into the mixture. Stirring was continued for 20 min and a solution of Et3N (0.12 mL, 0.89 mmol), compound (9) (0.2 g, 0.74 mmol) in anhydrous CH2Cl2 (20 mL) was added. After completion of the action, the reaction was quenched with dilute Na2CO3. The organic layer was washed with water and brine, and dried over Na2SO4. After filtration and concentration in vacuo, the residues was purified by silica gel flash chromatography (PE/AcOEt = 3:1) yielding (W1).

According to the analysis of related databases, 887267-47-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Su, Ping; Wang, Jinfeng; Shi, Yaling; Pan, Xiaoyan; Shao, Ruili; Zhang, Jie; Bioorganic and Medicinal Chemistry; vol. 23; 13; (2015); p. 3228 – 3236;,
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Application of 92028-21-2, 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. 92028-21-2 name is 6-Methoxy-[1,1′-biphenyl]-3-amine hydrochloride, This 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 6 N-(4-Methoxy-3-phenyl)phenyl-(2-chloro-5-nitrophenyl)carboxamide The title compound (0.586 g) was obtained as a crystalline solid according to the procedure described in Example 2 using (4-methoxy-3-phenyl)aniline hydrochloride (0.478 g), pyridine (5 ml) and 2-chloro-5-nitrobenzoyl chloride (0.535 g). 1H-NMR (400 MHz, CDCl3, TMS): delta(ppm) 3.95 (3H, s), 7.31-7.46 (4H, m), 7.63-7.69 (3H, m), 8.27 (1H, dd, J=8.8, 2.7 Hz), 8.67 (1H, d, J=2.7 Hz), 8.54 (1H, d, 2.2 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Methoxy-[1,1′-biphenyl]-3-amine hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; SANKYO COMPANY, LIMITED; US2003/134859; (2003); A1;,
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Related Products of 1036724-54-5, 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 1036724-54-5 as follows.

Six reactions were carried out in parallel and combined for work-up. To a solution of the product of the previous step (200 g, 711 mmol) in 15 THF (100 mL) was added 11 potassium carbonate (197 g, 1.4 mol). The reaction mixture was purged with nitrogen 3 times, followed by addition of Pd(dppf)Cl2-CH2Cl2 (11.6 g, 14.2 mmol). The reaction mixture was cooled to 0 C., diethylzinc (1 M, 1.07 L) was added drop-wise, and the reaction mixture was stirred at 70 C. for 1 h. The reactions were combined, cooled to 20 C. and poured into water (7 L) slowly. To the mixture was added aq. 4 M 16 HCl to pH 6. The organic layer was separated, and the aqueous phase was extracted with EtOAc (3×2 L). The combined organic layer was washed with brine (5 L), dried over sodium sulfate, concentrated, and purified through a silica gel pad (eluted with 50:1 17 petroleum ether:EtOAc)) to give the title intermediate (900 g, 92% yield) as a light yellow 18 oil. 1H NMR (400 MHz, CDCl3) delta 7.29-7.43 (m, 5H), 6.94-6.97 (m, 1H), 6.82 (d, J=8.0 Hz, 1H), 6.70 (m, 1H), 5.09 (s, 2H), 2.52-2.58 (m, 2H), 1.17 (t, J=7.6 Hz, 3H).

According to the analysis of related databases, 1036724-54-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; FATHEREE, PAUL R.; JIANG, LAN; MCKINNELL, ROBERT MURRAY; THALLADI, VENKAT R.; ZHANG, HAO; DABROS, MARTA; NZEREM, JERRY; BENJAMIN, NOAH; KLEINSCHEK, MELANIE A.; CRATER, GLENN D.; (40 pag.)US2018/311255; (2018); A1;,
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Application of 1236000-51-3, A common heterocyclic compound, 1236000-51-3, name is N-Methyl-1-(4-(trifluoromethoxy)phenyl)methanamine hydrochloride, molecular formula is C9H11ClF3NO, 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.

Intermediate 28 To a solution of 1.0 g of 3-iodobenzoic acid in 20 ml of CH2CI2 under argon atmosphere was added via cannula a solution of 1.11 g of DCC in 22 ml of CH2CI2. The resulting mixture was stirred for 1 h, then was added a solution of 0.65 g of Intermediate 1 and 0.414 ml of Et3N in 13 ml of CH2CI2. The resulting mixture was stirred overnight, diluted with Et2O, filtered off and the filter cake washed with Et2O. The filtrate was washed with 10% NaHCO3 and brine, dried over MgSO4, filtered and concentrated under vacuum. The residue was purified by chromatography on silica gel eluting with EtOAc-Hex 10:90 to 50:50 to afford 1.063 g (91 %) of the title compound as a colourless oil. 1H NMR (delta, ppm, CDCI3): 7.79 and 7.75 (s, 1 H); 7.39 (s, 1 H); 7.23 (d, 2H); 7.21-7.1 1 (m, 2H); 4.72 and 4.49 (s, 2H); 3.02 and 2.88 (s, 3H). [ES MS] m/z: 436 (MH+).

The synthetic route of 1236000-51-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; BUENO-CALDERON, Jose Maria; FERNANDEZ-MOLINA, Jorge; LEON-DIAZ, Maria Luisa; MALLO-RUBIO, Araceli; MANZANO-CHINCHON, M Pilar; WO2010/81904; (2010); A1;,
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Synthetic Route of 239122-51-1,Some common heterocyclic compound, 239122-51-1, name is 5-Bromo-3-fluoro-2-methoxyaniline, molecular formula is C7H7BrFNO, 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) N- (5-Bromo-3-fluoro-2-methoxy-phenyl)-2- [(E)-hydroxyiminol -acetamideIn a 500 ml three-necked flask, 2,2,2-trichloroethane-1,1-diol (8.68 g, 52.5 mmol) and sodium sulfate (47.4 g, 334 mmol) were combined with water (122 ml) to give a colorless solution. The reaction mixture was heated to 50 C and a mixture of 5-bromo-3-fluoro-2-methoxyaniline (CAS239122-51-1, 10.50 g, 47.7 mmol) in water (60 ml), dioxane (60 ml) and aqueous hydrochloricacid (7.84 ml, 95.4 mmol) were added. Then hydroxylamine hydrochloride (9.95 g, 143 mmol)in water (60 ml) was added. The reaction mixture was heated to 70 C and stilTed for 15 hoursand then cooled to room temperature. The precipitate was filtered off and washed with water (50ml) and dried in vacuo to yield the title compound as brown solid (13.4 g, 96 %). MS: mle =289.1, 291.3 [M-H].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-3-fluoro-2-methoxyaniline, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BISSANTZ, Caterina; BONNAFOUS, Rene; BUETTELMANN, Bernd; JAKOB-ROETNE, Roland; LERNER, Christian; RUDOLPH, Markus; WO2014/102233; (2014); A1;,
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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. 92028-21-2, name is 6-Methoxy-[1,1′-biphenyl]-3-amine hydrochloride, A new synthetic method of this compound is introduced below., COA of Formula: C13H14ClNO

Under nitrogen, compound X (from Example 38 part a) (5.0 g, 16.7 mmol) was mixed with toluene (80 mL) and 4-methoxy-3-phenylaniline hydrochloride (4.3 g, 18.3 mmol) was added to form a slurry. 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (1.6 g, 2.5 mmol) was added, followed by tris(dibenzylideneacetone)dipalladium(0) (760 mg, 0.83 mmol) and finally sodium tert-butoxide (5.3 g, 55 mmol). The mixture was heated at 90 C. for 150 min and then cooled to room temperature. Water (150 mL) was added followed by ethyl acetate (150 mL) and the phases partitioned. The aqueous layer was extracted with ethyl acetate (150 mL) and the combined organics washed three times with 0.5 M sodium bisulfate (200 mL), once with saturated sodium bicarbonate (150 mL) and twice with saturated sodium chloride (150 mL). The organics were dried over magnesium sulfate (50 g) and the volatiles removed under vacuum to give N-tert-butoxycarbonyl-2-[4-(3-[phenyl-4-methoxyphenyl)aminophenyl]ethylamine (LL) (8.4 g) which was used without further purification.

The synthetic route of 92028-21-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Moran, Edmund J.; Jacobsen, John R.; Leadbetter, Michael R.; Nodwell, Matthew B.; Trapp, Sean G.; Aggen, James; Church, Timothy J.; US2003/229058; (2003); A1;,
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Adding a certain compound to certain chemical reactions, such as: 239122-51-1, name is 5-Bromo-3-fluoro-2-methoxyaniline, belongs to ethers-buliding-blocks compound, 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 239122-51-1, Product Details of 239122-51-1

A solution of 2 (1 eq) and sodium carbonate (1.5 eq) in acetone was stirred in an ice bath under an atmosphere of nitrogen. Thiophosgene (1.5 eq) was added drop wise over 30 minutes. The reaction was stirred for another 30 minutes in the ice bath before being removed and allowed to warm to RT. The reaction was stirred at RT for 1.5 h before the reaction solution was concentrated under vacuum. Toluene was added to the crude product and removed under vacuum to azetrope off any residual thiophosgene and afford the product 3. MS: MH+=262

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.

Reference:
Patent; Amiri, Payman; Fantl, Wendy; Levine, Barry Haskell; Poon, Daniel J.; Ramurthy, Savithri; Renhowe, Paul A.; Subramanian, Sharadha; Sung, Leonard; US2004/122237; (2004); A1;,
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Synthetic Route of 166530-78-5, 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. 166530-78-5, name is (5-Bromo-2-methoxyphenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 5-bromo-2-methoxybenzaldehyde 11 (1 g, 4.65 mmol) and hydroxylaminehydrochloride (388 mg, 5.58 mmol) in ethanol (2.8 mL) was stirred for 1 h at room temperature.Subsequently, hydrochloric acid (12 M, 1.6 mL, 18.6 mmol) and zinc dust (760 mg, 11.62 mmol)slowly were added to the solution and the mixture was stirred at room temperature for 15 min. Asolution of ammonia (30%, 2.8 mL) and sodium hydroxide (6 M, 2.8 mL) was added dropwise tothe resulting slurry, and the mixture was stirred at room temperature for 15 min. Then, theresultant solution was extracted with CH2Cl2, dried over anhydrous sodium sulfate, and filtered.The solvent was removed under vacuum to afford the crude benzyl amine. The residue wasdissolved in CH2Cl2 (20 mL) which was then followed by the addition of Boc2O (1.52 g, 7.0mmol) and Et3N (710 mg, 7.0 mmol) at rt, the mixture was stirred for 2 h. After completion ofthe reaction, water was added into it, organic phase was separated and aqueous layer wasextracted with CH2Cl2 (3 × 20 mL). Organic phases were combined, washed with brine, driedover anhyd.Na2SO4 and concentrated to get crude boc-amine, which was then purified by columnchromatography (100-200 mesh size) using ethyl acetate:pet ether (1:9) as an eluent to affordpure boc-protected benzyl amine 12 (1.47 g).

The chemical industry reduces the impact on the environment during synthesis (5-Bromo-2-methoxyphenyl)methanamine. I believe this compound will play a more active role in future production and life.

Reference:
Article; Lalwani, Komal G.; Sudalai, Arumugam; Synlett; vol. 27; 9; (2016); p. 1339 – 1343;,
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Reference of 104750-60-9, 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. 104750-60-9, name is 2-Bromo-1-(methoxymethoxy)-4-methylbenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 4-(2-hydroxy-5-methylphenoxy)-3-methoxybenzoic acid (18o). The bromination of p-cresol, carried out via the method of Narender, et al.,3 was followed by MOM protection4 (96% yield over two steps). A solution of bis(pinacolato)diborane (2.5 g), dioxane (40 mL), KOAc (2.5 g) and the aryl bromide (6.5 mmol) was purged with nitrogen before Pd(dppf)Cl2 (0.47 g) was added. The mixture was refluxed overnight. Silica chromatography (gradient to 20% EtOAc/hexanes) gave the boronate ester (1.93 g), which was dissolved in acetone (20 mL) and treated with a solution of Oxone (4 g) in H2O (20 mL). After 10 min, NaHSO3 was added and the resulting solution was extracted with EtOAc. Silica chromatography (gradient up to 15% EtOAc/hexanes) gave 2-(methoxymethoxy)-5-methylphenol (0.578 g, 53% over two steps). The diaryl ether was prepared from the phenol and appropriate 4-fluorobenzalde using General Procedure D. Silica chromatography (gradient up to 40% EtOAc/hexanes) gave the intermediate aldehyde (481 mg, 47%). The oxidation was followed by MOM cleavage with conc. HCl (0.25 mL) in 50% THF/iPrOH (10 mL) to yield 18o (391 mg, 89% over two steps). 1H NMR (CDCl3) delta 7.73-7.66 (m, 2H), 6.99-6.85 (m, 3H), 6.76 (s, 1H), 3.97 (s, 3H), 2.24 (s, 3H).

The synthetic route of 2-Bromo-1-(methoxymethoxy)-4-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RESEARCH TRIANGLE INSTITUTE; Carroll, Frank I.; Thomas, James B.; Navarro, Hernan A.; Mascarella, S. Wayne; Runyon, Scott P.; Jin, Chunyang; Kormos, Chad M.; (20 pag.)US9512105; (2016); B2;,
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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. 888318-22-7, name is 1-Bromo-3,4-difluoro-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H5BrF2O

To a flask containing 1-bromo-3,4-difluoro-2-methoxy-benzene (1.0 g, 4.48 mmol) and 1,4-dioxa-8-azaspiro[4.5]decane (0.71 g, 4.93 mmol) in 1,4-dioxane (10 ml) was added tBuONa (1.3 g, 13.44 mmol), Pd2(dba)3 (82 mg, 0.09 mmol) and Ru-Phos (84 mg, 0.18 mmol)under N2. After being heated with stirring at 100 C overnight, the reaction mixture was cooled to rt, diluted with water (20 mL) and extracted with EA (30 mL) for three times. The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo to give 8- (3 ,4-difluoro-2-methoxy-phenyl)- 1 ,4-dioxa- 8-azaspiro [4.5] decane (0.74 g), which was used in the next step without further purification.

According to the analysis of related databases, 888318-22-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Min; YANG, Song; (208 pag.)WO2016/107832; (2016); A1;,
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