Author: Jessica.F

Electric Literature of 36865-41-5, 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 36865-41-5 as follows.

Step 1: Into a 500-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 1-bromo-3-methoxypropane (60 g, 393.0 mmol), triphenylphosphine (102.8 g, 393.1 mmol) and toluene (300 mL). The resulting solution was stirred for 16 h at 150 C. in an oil bath. The solids were collected by filtration. This resulted in (3-methoxypropyl)triphenylphosphonium bromide (120 g, 91% yield) as a white solid.

According to the analysis of related databases, 36865-41-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Enanta Pharmaceuticals, Inc.; Panarese, Joseph; Bartlett, Samuel; Chong, Katherine; Or, Yat Sun; (120 pag.)US2019/224188; (2019); A1;,
Ether – Wikipedia,
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Electric Literature of 768-70-7, 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. 768-70-7 name is 3-Ethynylanisole, 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 13 : 5-(3-Methoxyphenethyl)-l-(4-chloro-3-fluorobenzyl)pyridin- 2( 1 H)-OiIC (Final Compound 7-06); Step 1 : 5-(3-Methoxyphenethynyl)-2-methoxypyridine According to Scheme 8 Step 1 : Et3N (15eq, 12.0mmol, 1.68mL), PdCl2(PPh3)2 (0.05eq, 0.04mmol, 17.5mg), PPh3 (0.2eq, O.l?mmol, 41.8mg) and 5-bromo-2- methoxypyridine (leq, 0.80mmol, 0.15g) were added to a stirred solution of copper iodide (0.05eq, 0.04mmol, 7.6mg) in DMF (8mL). Then l-ethynyl-3-methoxybenzene (l.leq, 0.88mmol, 0.12g) was added and the mixture was heated under microwaves (120C/25min) and was stirred overnight at room temperature. The resulting solution was poured onto water and extracted with AcOEt. The combined organic layers were dried over MgSO4, filtered and evaporated under reduced pressure. The crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 25g SiO2) using pentane/Et2O 98/2 as eluent to afford 5-(3- methoxyphenethynyl)-2-methoxypyridine (0.64mmol, 154mg, 81%) as a colorless oil. LC (XTerra RP18, 3.5mum, 3.0x50mm Column): RT = 5.13 min; MS m/z ES+= 240.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Ethynylanisole, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; ADDEX PHARMACEUTICALS S.A.; WO2006/30032; (2006); A1;,
Ether – Wikipedia,
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Some common heterocyclic compound, 651734-54-2, name is 2,6-Difluoro-3,5-dimethoxyaniline, molecular formula is C8H9F2NO2, 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. SDS of cas: 651734-54-2

Example 451-Cyclopropyl-3-(2,6-difluoro-3,5-dimethoxyphenyl)-1,3,4,7-tetrahydro-2H- pyrrolo j3?,2?:5,6j pyrido 14,3-djpyrimidin-2-one Step 1: N-[(JE)-(4-chloro-JH-pyrrolo[2, 3-bJpyridin-5-yl)methyleneJ-2, 6-d ifluoro-3 , 5- dimethoxyaniline A mixture of 4-chloro- 1 H-pyrrolo[2,3 -b]pyridine-5 -carbaldehyde (5.00 g, 27.7 mmol), 2,6-difluoro-3,5-dimethoxyaniline (6.3 g, 33 mmol) and p-toluenesulfonic acid monohydrate (1.1 g, 5.8 mmol) in toluene (300 mL) was heated to reflux with azeotropic removal of water via a Dean-Stark trap. After stirred for overnight, the reaction mixture wasconcentrated and the residue was used in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 651734-54-2, its application will become more common.

Reference:
Patent; INCYTE CORPORATION; WU, Liangxing; ZHANG, Colin; HE, Chunhong; SUN, Yaping; LU, Liang; QIAN, Ding-Quan; XU, Meizhong; ZHUO, Jincong; YAO, Wenqing; WO2014/7951; (2014); A2;,
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These common heterocyclic compound, 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine, 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. Recommanded Product: 93919-56-3

A solution of the ethyl 3-(3,5-dibromo-4-hydroxyphenyl)-1,2,4-oxadiazole-5-carboxylate (78 mg, 0.2 mmol) plus 4-trifluoromethoxybenzyl amine (57 mg, 0.3 mmol) in ethanol (3 mL) was refluxed for 6 hours. The resulting solution was evaporated in vacuo and the residue was dissolved in ethyl acetate (2.5 mL) and washed with 1 N hydrochloric acid (2 mL), then water (2 mL). The organic layer was evaporated to dryness in vacuo and purified by preparative HPLC to give the title compound (57 mg, 53%) as a colourless powder. 1H NMR delta (ppm) (DMSO-d6): 4.55 (2H, d), 7.38 (2H, d), 7.51 (2H, d), 10.07 (1H, t), 10.95 (1H, s, br). LCMS (10 cm_apci_formic) tR4.14 min; m/z 534/536/538 [M-H]-.

The synthetic route of (4-(Trifluoromethoxy)phenyl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Institute for OneWorld Health; US2009/318429; (2009); A1;,
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Reference of 24332-20-5,Some common heterocyclic compound, 24332-20-5, name is 1,1,2-Trimethoxyethane, molecular formula is C5H12O3, 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 1,1,-2-trimethoxyethane (2.07 [ML,] 16.07 [MMOL)] in 0.5M HCI (32 mL) was heated at [100C] for 2 h. The cooled mixture was extracted with [CH2C12] (30 mL) and the organic solution dried (3A molecular sieves). 3-Bromo-2-methylphenylamine was added and the resultant solution stirred under nitrogen for 20 min. Acetic acid (461 [UL,] 8.05 [MMOL)] and sodium triacetoxyborohydride (4.78g, 22.56 [MMOL)] were added and the reaction mixture stirred under nitrogen at room temperature for 16 h. Saturated sodium bicarbonate (60 mL) was added portionwise and the resultant mixture stirred for 0.5 h and extracted with CH2CI2 (2 x 100 mL). The organic solution was dried [(NA2SO4)] and the solvents removed in vacuo. Purification by SPE (silica, 2 x 20g) eluted with 100: 2 to 100: 5 cyclohexane : EtOAc afforded the title compound as a yellow oil (687mg). LC/MS: [M/Z] 246 [M+H] +, Rt 3.27 min.

The synthetic route of 24332-20-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2004/762; (2003); A2;,
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Adding a certain compound to certain chemical reactions, such as: 710-18-9, name is 1-Methoxy-4-(trifluoromethoxy)benzene, 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 710-18-9, HPLC of Formula: C8H7F3O2

To 4-methoxy-trifluoromethoxybenzene (0.19 g, 0. [001] mol) in 5 mL acetonitrile was added nitronium tetrafluoroborate (0.146 g, 0.001 mol) at room temperature. After about 6 h, another 0.25 equivs of nitronium tetrafluoroborate was added and the reaction stirred overnight. The reaction was then concentrated in vacuo, and the residue was partitioned between ether and water. The aqueous phase was washed [TWICW] with ether, then the combined organic layers were washed with water, and dried over MgS04. The solvent was removed, resulting in a mobile oil. Kugelrohr distillation of the oil provided 0.2 g of the desired nitrated intermediate which was collected at [100-125 C.]

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, 1-Methoxy-4-(trifluoromethoxy)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM PHARMACEUTICALS, INC.; WO2004/14870; (2004); A1;,
Ether – Wikipedia,
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Related Products of 2734-70-5, The chemical industry reduces the impact on the environment during synthesis 2734-70-5, name is 2,6-Dimethoxyaniline, I believe this compound will play a more active role in future production and life.

To an ice-cooled solution of 2,6-dimethoxyaniline (Amfinecom Inc., 1.2 g, 7.8 mmol) in DCM (20 mL) was added N,N-diisopropylethylamine (2.73 mL, 15.7 mmol) via syringe followed by a solution of 1,3-thiazole-2-carbonyl chloride (Maybridge, 1.16 g, 7.9 mmol) in DCM (27 mL) slowly via cannula. The resulting brown solution was allowed to warm to RTand stirred for 19 h. The reaction was then partitioned between water (80 mL) and DCM (2X). The combined organic layers were washed with brine (2X), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (eluent: 10-100percent EtOAc in hexanes) to provide 396.1 (1.30 g, 63percent yield) as a light yellow solid. LCMS-ESI (pos.) m/z: 265.2 (M+H)+.

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, 2,6-Dimethoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEUMANN, Lars V.; HORNE, Daniel B.; HOUZE, Jonathan; KALLER, Matthew R.; KAYSER, Frank; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; MEDINA, Julio C.; MIHALIC, Jeffrey T.; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; WANSKA, Malgorzata; YANG, Kevin; YEH, Wen-Chen; (700 pag.)WO2018/97945; (2018); A1;,
Ether – Wikipedia,
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Reference of 14869-41-1, These common heterocyclic compound, 14869-41-1, name is 2-(2-Chloroethoxy)acetic acid, 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.

In a glass RBF equipped with a Teflon-coated magnetic stirrer was dissolved 4-fluoro-2-methoxy-5- nitro-phenylamine (1 eq.) in DMF (0.32 M). To this was then added sequentially HATU (1.2 eq.), DMAP (0.1 eq.), (2-chloro-ethoxy)-acetic acid (1.1 eq.) and finally ethyl-diisopropylamine (3 eq.). When the reaction was deemed to be complete by LCMS (14 h), the reaction mixture was diluted with EtOAc and washed sequentially with 10percent aq. HC1, sat. aq. NaHCO3, water and brine. The organic extract was then dried over MgSO4 and filtered. Concentration of the filtrate thus obtained in vacuo furnished the desired product as a tan solid (99percent yield).

The synthetic route of 14869-41-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; JORAND-LEBRUN, Catherine; LAN, Ruoxi; CHEN, Austin; CLARK, Ryan C.; (268 pag.)WO2017/49068; (2017); A1;,
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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. 168268-00-6, name is 4-(Benzyloxy)-3-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C13H12FNO

To a stirred mixture of 4-benzyloxy-3-fluoro-phenylamine (33.7 g, 155.3mmol), 1-(4-fluoro-phenylcarbamoyl)-cyclopropane carboxylic acid (38.13 g, 170.8mmol) and anhydrous DCM (600 ml) was added EDCI (44.7 g, 233.9mmol) in portions. After stirring at r.t. for 1 h, the reaction mixture was diluted with saturated sodium bicarbonate (400 ml) and stirred for 30 minutes. The precipitate was filtered and air dried to give the 1st crop of product. The biphasic filtrate was separated, and the organic phase was washed with brine (300 ml), dried over anhydrous sodium sulfate, and concentrated. The residue was taken up in DCM (100 ml), stirred for 15 minutes, and filtered to give a 2nd crop of product. The combined yield of Cyclopropane-1,1-dicarboxylic acid (4-benzyloxy-3-fluoro-phenyl)-amide(4-fluoro-phenyl)-amide 64.5 g, yield: 98%. 1H-NMR (300MHz, CDCl3) delta: 8.9 (m, 2H), 7.35-7.18 (m, 8H), 6.95-6.85 (m, 4H), 5.03 (s,2H), 1.53(s, 2H).

According to the analysis of related databases, 168268-00-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Li, Jieming; Gu, Weijie; Bi, Xinzhou; Li, Huilan; Liao, Chen; Liu, Chunxia; Huang, Wenlong; Qian, Hai; Bioorganic and Medicinal Chemistry; vol. 25; 24; (2017); p. 6674 – 6679;,
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Related Products of 3616-56-6,Some common heterocyclic compound, 3616-56-6, name is 2,2-Diethoxy-N,N-dimethylethanamine, molecular formula is C8H19NO2, 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.

Synthesis of 3-bromo-12H-benzofuranyl[2,3-a]carbazole (compound 9); (9); Under nitrogen, compound 8 (1 .3 g, 1 eq.) is initially charged and dissolved with acetic acid (55 ml) while heating to reflux. Then (dimethylamino)acetaldehyde diethyl acetal (95percent; 7.1 g, 10 eq.) is added dropwise to the reaction within 1 .5 h and the mixture is stirred at reflux for a further 7 h. It is stirred at room temperature overnight. The next day, it is heated back to reflux and a further 2 g of (dimethylamino)acetaldehyde diethyl acetal are added dropwise. After 6 h at reflux, a further 4 g (dimethylamino)acetaldehyde diethyl acetal are added dropwise and it is stirred for a further 7.5 h. The mixture is cooled to room temperature and diluted with methylene chloride. Washed in a separating funnel with distilled water and then with saturated NaCI. The organic phase is dried with sodium sulfate and concentrated. LC (C18-Si02, acetonitrile) gives 0.33 g of product (24percent yield). 1H NMR (CD2CI2, 400 MHz): “5 = 8.7 (br s, 1 H), 8.15 (d, 2H), 8.06 (d, 1 H), 7.78 (d, 1 H), 7.60 (m, 3H), 7.48 (dd, 1 H), 7.32 (dd, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,2-Diethoxy-N,N-dimethylethanamine, its application will become more common.

Reference:
Patent; BASF SE; BASF (CHINA) COMPANY LIMITED; KONINKLIJKE PHILIPS ELECTRONICS N.V.; OSRAM OPTO SEMICONDUCTORS GMBH; PHILIPS INTELLECTUAL PROPERTY & STANDARDS GMBH; LANGER, Nicolle; SCHILDKNECHT, Christian; WATANABE, Soichi; FUCHS, Evelyn; WAGENBLAST, Gerhard; LENNARTZ, Christian; MOLT, Oliver; DORMANN, Korinna; HUNZE, Arvid; KRAUSE, Ralf; SCHMID, Guenter; HEUSER, Karsten; VAN ELSBERGEN, Volker; BOERNER, Herbert Friedrich; WO2011/125020; (2011); A1;,
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