Tag: M.W=200-300

Related Products of 2982-54-9,Some common heterocyclic compound, 2982-54-9, name is 2-(4-(Benzyloxy)phenyl)ethanamine hydrochloride, molecular formula is C15H18ClNO, 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 100 ml flask as added lH-pyrrolo[3,2-c]pyridine-2-carboxylic acid (100 mg and 0.617 mmol) 2-(4-(benzyloxy)phenyl)ethanamine HC1 (195 mg, 0.740 mmol) in DMF (10 ml) to give a light yellow suspension. HATU (352 mg, 0.925 mmol) and DIEA (319 mg, 2.467 mmol) were added. The mixture was stirred at RT for 16 hours. Added water and extracted with ethyl acetate (3 x 20 mL). The organic layers were combined and washed with water (3 x 20 mL). The organic was separated, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure The Biotage purification affordedl40 mg of the product (61%). ¾ NMR (DMSO-d6). delta 13.00 (s, 1H), 9.30 (s, 1H), 9.00 (m, 1H), 8.37 (d, H), 7.78 (d, 1H), 7.52(s, 1H), 7.30-7.47 (m, 5H), 7.18(d, 2H), 6.90(d, 2H), 5.02(s, 2H), 3.37(m, 2H0, 2.80(m, 2H). LC-MS: 472.25 (M+l)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(4-(Benzyloxy)phenyl)ethanamine hydrochloride, its application will become more common.

Reference:
Patent; FORMA TM, LLC; BAIR, Kenneth W.; BAUMEISTER, Timm; BUCKMELTER, Alexandre J.; CLODFELTER, Karl H.; HAN, Bingsong; KUNTZ, Judith D.; LIN, Jian; REYNOLDS, Dominic J.; SMITH, Chase C.; WANG, Zhongguo; ZHENG, Xiaozhang; WO2012/154194; (2012); 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. 202865-58-5, name is 1-Bromo-4,5-difluoro-2-methoxybenzene, A new synthetic method of this compound is introduced below., COA of Formula: C7H5BrF2O

To a flask containing 1-bromo-4,5-difluoro-2-methoxy-benzene (1.1 g, 4.93 mmol) and 1,4-dioxa-8-azaspiro[4.5]decane (0.78 g, 5.43 mmol) in 1,4-dioxane (10 mL) was added tBuONa (1.18 g, 12.33 mmol), Pd2(dba)3(92mg, 0.10 mmol) and Ru-Phos (92mg, 0.20 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- (4,5-difluoro-2-methoxy-phenyl)- 1 ,4-dioxa- 8-azaspiro [4.5] decane (1.31 g), which was used in the next step without further purification.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

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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Related Products of 1000574-79-7, A common heterocyclic compound, 1000574-79-7, name is 2-Bromo-4-(difluoromethoxy)aniline, molecular formula is C7H6BrF2NO, 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.

(25a) N-[2-Bromo-4-(difluoromethoxy)phenyl]formamide Into acetonitrile (80 mL), 2-bromo-4-(difluoromethoxy)aniline (4.40 g, 18.5 mmol) and formic acid (1.1 mL, 27.5 mmol) were dissolved, to which 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (7.7 g, 28 mmol) and 4-methylmorpholine (3 mL, 27 mmol) were added, followed by stirring at room temperature for six hours. Ethyl acetate and water were added for extraction, and the resulting organic layer was sequentially washed with water and saturated brine and then dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure and the residue thus obtained was purified by silica gel column chromatography (hexane : ethyl acetate, 100 : 0 – 60 : 40, V/V) to give the desired title compound (4.1 g, yield 83%). 1H-NMR (CDCl3) 5: 6.47 (1H, t, J = 73.0 Hz), 7.13 (1H, dd, J = 9.1, 2.6 Hz), 7.39 (1H, d, J = 2.6 Hz), 7.58 (1H, br s), 8.41 (1H, d, J = 9.1 Hz), 8.49 (1H, s).

The synthetic route of 1000574-79-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daiichi Sankyo Company, Limited; AOKI, Kazumasa; MATSUI, Satoshi; YOSHIKAWA, Kenji; SHIMIZU,Hiroki; SASAKI, Junko; NAKAJIMA, Katsuyoshi; KANNO, Osamu; OIZUMI, Kiyoshi; EP2565185; (2013); A1;,
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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 33839-11-1 as follows. category: ethers-buliding-blocks

3-EthyI-4-methoxyphenylboronic acid 6. To a stirred solution of 4-bromo-2-ethyl-l-methoxybenzene (4.59 g, 21 mmol) in dry THF (50 mL)5 cooled to -78C5 was added slowly drop-wise (over 45 min) n-BuLi (15 mL of a 1.6 M solution in hexanes, 24 mmol). The solution was stirred at -78C for 2 h before trimethylborate (3.6 mL, 31.5 mmol) was added drop-wise and the reaction was allowed to warm slowly to rt with stirring overnight. The reaction was quenched with 2M HCl (50 mL) and the products extracted with EtOAc (2 x 50 mL). These extracts were combined and concentrated under reduced pressure to give an oily substance. To this was added hexane followed by a small amount of DCM and the resulting white precipitate was collected by filtration and washed with hexane. Yield 1.55 g, 41%: 1H NMR delta (270 MHz, CDCl3) 1.27 (3H, t, J= 7.5 Hz)5 2.73 (2H5 q, J = 7.5 Hz)5 3.90 (3H5 s), 6.60 (-1H5 bs), 6.96 (IH5 d, J = 8.4 Hz)5 7.98 (IH5 d5 J = 1.5 Hz)5 8.08 (IH5 dd, J = 8.2, 1.7 Hz); LC/MS (APCI) m/z 179.04 (M-H)”; HPLC ttau = 2.1 min (>99%) 90% MeCN in H2O.

According to the analysis of related databases, 33839-11-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; STERIX LIMITED; WO2007/96647; (2007); A2;,
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Reference of 104750-60-9, The chemical industry reduces the impact on the environment during synthesis 104750-60-9, name is 2-Bromo-1-(methoxymethoxy)-4-methylbenzene, I believe this compound will play a more active role in future production and life.

A solution of 9-bromoanthracene (0.67 g, 2.6 mmol, 1.2 eq) in dry Et2O (13 mL) under N2 was cooled to -30 C and “Buli (1.6 M in hexane, 1.6 mL, 2.6 mmol, 1.2 eq) was added dropwise. The solution was stirred for 20 min. at -30 C followed by dropwise addition of ZnCl2 (0.50 M in THF, 5.2 mL, 2.6 mmol, 1.2 eg). The reaction was stirred and warmed to RT over 30 min. The volatiles were removed under N2 purge and the residue was redissolved in 3:1 THF/NMP (11 mL). The MOM-protected bromophenol (2.2 mmol, 1.0 eg) and Pd(PtBu3)2 (22 mg, 44 mumol, 4 mol %) were added and the reaction was heated to 100 C for 2 h. The reaction was cooled to RT and the THF was removed. The residue was diluted with CH2C12, washed with 1 M HCI, and dried over Na2S04. The crude material was purified by flash chromatography. Synthesized by General Method Cl. Purified by flash chromatography (Biotage FLASH 40S KP-Sil silica, 0-5% EtzO/hexanes) to yield 0.59 g (84%) of 31 as a white solid. ?H NMR (CDCl3,300 MHz): 8.48 (s, 1H), 8.03 (d, J= 8.7 Hz, 2H), 7.65 (dd, J= 8.7 Hz, J = 0.6 Hz, 2H), 7.50-7.20 (m, 6H), 7.09 (d, J= 1.8 Hz, 1H), 4.84 (s, 2H), 3.00 (s, 3H), 2.38 (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, 2-Bromo-1-(methoxymethoxy)-4-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SYMYX TECNOLOGIES, INC; WO2005/108406; (2005); 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. 31963-35-6, name is 1-(2-Phenoxyphenyl)methanamine hydrochloride, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-(2-Phenoxyphenyl)methanamine hydrochloride

Example 95: 4-Chloro-6-(2-phenoxy-benzyIamino)-2H-phthalazin-l-one; A mixture 6-bromo-4-chloro-2H-phthalazin-l-one (150 mg, 0.58 mmol), 2- phenoxy-benzylamine hydrochloride (151 mg, 0.64 mmol), Pd2(dba)3 (53 mg, 0.058 mmol), rac-BINAP (132 mg, 0.17 mmol) and NaOt-Bu (200 mg, 2.1 mmol) in DMA (6 mL) was heated at 8O0C for Ih. The mixture was allowed to cool, diluted with EtOAc (25 mL) and washed with water (25 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated. Chromatography on silica (EtOAc/hexanes) yielded the title compound. 4-Chloro-6-(2-phenoxy-benzylamino)-2H-phthalazin-l-one: 81 mg (37.0%): m/z (M+eta)=378. 1H-NMR (DMSO-J5) delta: 12.77 (s,lH), 8.34 (d,lH), 8.03(m,lH), 7.82 (m,3H), 7.71 (m,lH), 7.56 (m,3H), 7.42 (m,2H), 7.33 (dd,lH), 7.20 (s,lH), 4.84 (d,2H).

The synthetic route of 31963-35-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FOREST LABORATORIES HOLDINGS LIMITED; WO2008/61108; (2008); A2;,
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Application of 35202-55-2, 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. 35202-55-2, name is (3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methanamine hydrochloride belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1.5 mL of ethyl chloroformate are poured into a suspension of 3.4 g of the compound obtained in Step 1 in 4.5 mL of triethylamine and 50 mL of dichloromethane and left overnight, whilst stiffing at ambient temperature; washing with water and with 1N hydrochloric acid is then carried out. Drying is carried out and the solvent is evaporated off to dryness. 3.2 g of an oil corresponding to the expected product are obtained. Yield=80%

The synthetic route of (3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methanamine hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LES LABORATOIRES SERVIER; CARRANZA, Maria Del Pilar; GARCIA ARANDA, Maria Isabel; GONZALEZ, Jose Lorenzo; SANCHEZ, Frederic; US2014/107334; (2014); A1;,
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Related Products of 887267-47-2, 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. 887267-47-2 name is 2-Bromo-5-(trifluoromethoxy)aniline, 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.

To a solution of 2-bromo-5-(trifluoromethoxy)aniline (1.00 g, 3.91 mmol, 1.0 eq) in DCM (10 mL) was added TEA (800.0 mg, 7.91 mmol, 1.10 mL, 2.02 eq) and acetyl chloride (620.0 mg, 7.90 mmol, 563.6 muL, 2.02 eq) at 0 C. After 5 h at 0 C, the mixture was warmed to 40 C and stirred for another 7 h under N2. The reaction mixture was poured into H2O (150 mL), and extracted with EtOAc (50 mL*3). The combined organic layers were washed with brine (80 mL), dried over anhydrous Na2SO4, filtered and the filtrate was concentrated in vacuum. The residue was purified by column chromatography (SiO2) to give compound 06-59-1 (900.0 mg, 2.33 mmol, 60% yield). M+H+ = 297.0 (LCMS).1H NMR (CDCl3, 400 MHz): delta 8.41 (br s, 1H), 7.55 (d, J = 8.8 Hz, 1H), 6.88 (dd, J = 1.8, 8.8 Hz, 1H), 2.27 (s, 3H)

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

Reference:
Patent; KYRAS THERAPEUTICS, INC.; VACCA, Joseph P.; LI, Dansu; (587 pag.)WO2017/96045; (2017); A1;,
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Application of 92028-21-2,Some common heterocyclic compound, 92028-21-2, name is 6-Methoxy-[1,1′-biphenyl]-3-amine hydrochloride, molecular formula is C13H14ClNO, 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 compound JJ hydrochloride (73.7 g, 114 mmol) and 4-methoxy-3-phenylaniline hydrochloride (32.4 g, 137 mmol), toluene (380 mL) was added with mild agitation for 5 minutes, followed by sodium tert-butoxide (49.3 g, 513 mmol) in portions over 1 minute, and finally 2,2′-bis(diphenylphosphino)-11beta-binaphthyl (10.65 g, 17 mmol) and tris(dibenzylideneacetone)dipalladium(0) (5.22 g, 5.7 mmol). The resulting mixture was stirred and heated to 85-89 C. (internal) for 2.5 hours. The solution was cooled to room temperature, water (400 mL) was added and the mixture was stirred for 5 minutes, filtered through Celite (80 g), and partitioned with toluene (100 mL). The organic layer was collected and concentrated under reduced pressure in a 40 C. bath to give N-{2-[4-(3-phenyl-4-methoxyphenyl)aminophenyl]ethyl}-(R)-2-tert-butyldimethylsilyl-2-(8-benzyloxy-2(1H)-quinolinon-5-yl)ethylamine (NN) as a dark viscous oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Methoxy-[1,1′-biphenyl]-3-amine hydrochloride, its application will become more common.

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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Some common heterocyclic compound, 439814-87-6, name is 4-Bromo-1-(dimethoxymethyl)-2-fluorobenzene, molecular formula is C9H10BrFO2, 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. name: 4-Bromo-1-(dimethoxymethyl)-2-fluorobenzene

4-Bromo-1-(dimethoxymethyl)-2-fluorobenzene (87.0 g, 349.27 mmol) was dissolved in THF (700 mL) and cooled to -78 C. n-Butyl lithium (185.42 mL of a 2.5 M soln in hexanes, 461.04 mmol) was rapidly added and immediately followed by addition of DMF (40.40 mL, 523.91 mmol). Reaction was stirred in the cold for 30 min then allowed to warm to rt and stirred for 1 h. The reaction solution was diluted with H2O (500 mL) and extracted with Et2O (3*500 mL). The combined organic extracts were washed with brine (3*200 mL), dried (Na2SO4), filtered, concentrated and chromatographed (eluted with 10% EtOAc in hexanes) to provide 45.90 g of 4-(dimethoxymethyl)-3-fluorobenzaldehyde as a clear oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 439814-87-6, its application will become more common.

Reference:
Patent; Pfizer Inc; US2006/58361; (2006); A1;,
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