Tag: M.W=100-200

Synthetic Route of 126829-31-0,Some common heterocyclic compound, 126829-31-0, name is 2-Ethynyl-1,3-dimethoxybenzene, molecular formula is C10H10O2, 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.

General procedure: A THF solution (0.2 mL) of PdCl2(MeCN)2 (3.9 mg, 0.015 mmol) and 2b (10.2 mg, 0.015 mmol) was stirred for 10 min. To the solution were added diiodoparacyclophane 6 (0.05 mmol) in THF (0.8 mL), i-Pr2NH (0.2mL), alkyne 7 (0.2 mmol) and CuI (2.9 mg, 0.015 mmol) in order. The resulting mixture was stirred at room temperature. After the reaction was complete, H2O was added to the reaction mixture, and organic materials were extracted with AcOEt. The organic layer was washed with brine and dried with Na2SO4. The solvent was removed under reduced pressure, and the crude products were purified by thin-layer chromatography to give dialkynylated product 8.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Ethynyl-1,3-dimethoxybenzene, its application will become more common.

Reference:
Article; Kanda, Kazumasa; Oshima, Shoya; Shizuno, Tsubasa; Hamanaka, Risa; Fukai, Miku; Shibata, Takanori; Heterocycles; vol. 8; 2; (2014); p. 1355 – 1370;,
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Electric Literature of 20781-20-8, A common heterocyclic compound, 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, molecular formula is C9H13NO2, 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.

General procedure: The 6-chloronicotinic acid (2g, 12.73 mmol) was dissolved inDMF (20 ml). In the prepared solution, TBTU (4.90 g, 15.28 mmol)and TEA (2.66 mL, 19.10 mmol) was added. The reaction mixture was stirred for 30 min at room temperature. An amine(12.73 mmol) was added and stirred for 3 h at room temperature.The progress of the reaction was monitored by TLC. The reactionmixture was then quenched with crushed ice (50g) and stirred for30 min. The obtained precipitate was filtered and dried. Finally the product was purified by column chromatography using ethyl acetate:petroleum ether as eluent. Yield: (2a:87%, 2c:86%, 2l: 88%).

The synthetic route of 20781-20-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Thirunavukarasu, Jayaprakash; Begam, Rosina; Shajahan; Journal of Molecular Structure; vol. 1196; (2019); p. 518 – 526;,
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Related Products of 41789-95-1, These common heterocyclic compound, 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, 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.

General procedure: A mixture of 2.73 mmol appropriate alkyl halide (i.e., 17a-c, or18a-c), 0.6 g K2CO3 (4.34 mmol), and 0.6 g NaI (4.00 mmol) in ACN(12 mL) was mixed for 5 min in a 30 mL microwave reaction vessel.Then, 8.2 mmol appropriate amine derivative (i.e., 1-6, as shown inScheme 3) was added and the resulting content was mixed foradditional 2 min. The reaction vessel was capped, and insertedinside the microwave instrument (i.e., A CEM Model Single ModeMicrowave Instrument) and heated for 32 min at 105 C at thedynamic mode of the instrument automatically calibrating theradiation and temperature balance with respect to the change inpressure. Then, acetonitrile was distilled out under vacuum andthe residue thus obtained was mixed with 20 mL of K2CO3 solution(5.0%) and this mixture was heated at 60 C for 1 h. Then the mixturewas cooled down to room temperature and the aqueous phasewas extracted 3 times with 20 mL of ethylacetate. Combinedorganic extracts were dried over MgSO4 and concentrated underreduced pressure to give the product (i.e., free base). The free basewas dissolved in 10 mL acetone and HCl gas was continuouslypassed until HCl salt precipitation took place.

Statistics shows that 1-(3-Methoxyphenyl)-N-methylmethanamine is playing an increasingly important role. we look forward to future research findings about 41789-95-1.

Reference:
Article; Gulcan, Hayrettin Ozan; Unlu, Serdar; Esiringu, Ilker; Ercetin, Tugba; Sahin, Yasemin; Oz, Demet; Sahin, Mustafa Fethi; Bioorganic and Medicinal Chemistry; vol. 22; 19; (2014); p. 5141 – 5154;,
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Some common heterocyclic compound, 2734-70-5, name is 2,6-Dimethoxyaniline, molecular formula is C8H11NO2, 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: 2734-70-5

[015581 3-isothiocyanato-2,4-dimethoxypyridine, Example 771.1. A 2L round bottom flask was charged with 1,1?-thiocarbonyldi-2(1H)-pyridone (47.0 g, 202 mmol) and dissolved in dry DCM (405 mL). To that solution was added 2,6- dimethoxyaniline (31 g, 202 mmol) dissolved in DCM (405 mL) via an addition funnel at RT over 40 minutes. After 16 hours, the reaction was concentrated in vacuo and purified on silica gel (0-20percent EtOAc in heptanes) to give 2-isothiocyanato-1,3-dimethoxybenzene (32 g, 164 mmol, 81 percent yield). LCMS-ESI (POS.) mlz: 197.1 (M+H)t

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2734-70-5, its application will become more common.

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; HEATH, Julie Anne; HORNE, Daniel B.; HOUZE, Jonathan; KALLER, Matthew R.; KHAKOO, Aarif Yusuf; KOPECKY, David John; LAI, Su-Jen; MA, Zhihua; MCGEE, Lawrence R.; MEDINA, Julio C.; MIHALIC, Jeffrey T.; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; YANG, Kevin; YEH, Wen-Chen; DEBENEDETTO, Mikkel V.; FARRELL, Robert P.; HEDLEY, Simon J.; JUDD, Ted C.; KAYSER, Frank; (1266 pag.)WO2016/187308; (2016); A1;,
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Synthetic Route of 33170-72-8, The chemical industry reduces the impact on the environment during synthesis 33170-72-8, name is 2-Bromo-1,1-dimethoxypropane, I believe this compound will play a more active role in future production and life.

A mixture of compound 2-bromofuranylpropionaldehyde dimethyl acetal (1.0 g, 4.74 mmol) and hydrochloric acid (1 M, 3 mL) was heated to 90C and stirred for 1 hour. The reaction solution was cooled to room temperature and then neutralized to pH of 7 with a solid of sodium bicarbonate. Then 2-amino-5-bromopyridine (360 mg, 2.08 mmol) and methanol (5 mL) were added successively, and the reaction solution was heated to 90C and stirred overnight. The reaction solution was evaporated under reduced pressure to remove the organic solvent, diluted with water (10 mL) and dichloromethane. The organic layer was seperated, washed with water, saturated brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure to give a crude product, which was purified by silica gel column chromatography to give compound 31-a as a gray solid (250 mg, 57%). LC-MS (ESI): m/z = 210.9 [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-Bromo-1,1-dimethoxypropane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shanghai Yingli Pharmaceutical Co. Ltd.; XU, Zusheng; LOU, Yangtong; CHEN, Li; (95 pag.)EP3492461; (2019); A1;,
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Related Products of 145903-31-7, These common heterocyclic compound, 145903-31-7, name is 7-Methoxy-2,3,4,5-tetrahydrobenzo[f][1,4]thiazepine, 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.

Novel compounds of this general structure were prepared by reacting 7-methoxy-2,3,4,5-tetrahydro-1,4-benzothiazepine (1) with triphosgene, in the presence of a base (Et3N), followed by addition of a primary or secondary amine or an alcohol. A representative synthesis of this general process is depicted in Scheme 6 below.

Statistics shows that 7-Methoxy-2,3,4,5-tetrahydrobenzo[f][1,4]thiazepine is playing an increasingly important role. we look forward to future research findings about 145903-31-7.

Reference:
Patent; Marks, Andrew R.; Landry, Donald W.; Deng, Shi Xian; Cheng, Zhen Zhuang; US2005/215540; (2005); A1;,
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Application of 658-89-9, 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. 658-89-9 name is 4-(Trifluoromethoxy)benzene-1,2-diamine, 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.

Intermediate 41 : Mixture of (trans) N-{2-amino-4-[(trifluoromethyl)oxy1phenyl)-3-(4- fluorophenyl)-2-oxo-1-oxa-3-azaspiro[4.51decane-8-carboxamide and (trans) N-{2-amino- 5-[(trifluoromethyl)oxy1phenyl)-3-(4-fluorophenyl)-2-oxo-1-oxa-3-azaspiro[4.51decane-8- carboxamide; 4-[(Trifluoromethyl)oxy]-1 ,2-benzenediamine (Intermediate 32, 177 mg, 0.921 mmol) and (trans) 3-(4-fluorophenyl)-2-oxo-1-oxa-3-azaspiro[4.5]decane-8-carboxylic acid (Intermediate 42, 180 mg, 0.614 mmol) were dissolved in pyridine (2.5 ml) and EDC (188 mg, 0.982 mmol) was added. The mixture was stirred at r.t. for 2 hours. The pyridine was removed under vacuum and the residue partioned between aq. sat. NaHCO3 (20 ml) and EtOAc (50 ml). The aqueous layer was extracted once again with EtOAc (30 ml). The combined EtOAc extracts were washed with brine (20 ml), dried (Na2SO4), filtered and evaporated. The residue was purified by silica gel chromatography eluting with cyclohexaneEtOAc 64 to 46. The title compounds were obtained as a mixture of both possible regioisomers and were collected together to give 274.5 mg (0.529 mmol, 86%). 1 H-NMR (400 MHz, CDCI3): (data given for major isomer) delta 7.54 (2H, dd), 7.18-7.25 (1 H, m), 7.19 (2H, t), 6.64-6.73 (1 H, m), 3.77 (2H, s), 2.48-2.58 (1 H, m), 2.10-2.23 (4H, m), 1.80-2.00 (4H, m), one aromatic proton not detected, might fall underneath CHCI3 signal; UPLC-MS: 0.75 min, 468 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(Trifluoromethoxy)benzene-1,2-diamine, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/129007; (2008); A1;,
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Synthetic Route of 768-70-7, 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. 768-70-7, name is 3-Ethynylanisole belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step B:; In nitrogen atmosphere, the above ester (115 mg, 0.25 mmol) and 1-ethynyl-3- methoxybenzene (97 muL, 0.75 mmol) were dissolved in anhydrous tetrahydrofuran (4 mL). 0.15 M Solution of tri-tert-butylphosphine in cyclohexane (0.2 mL, 0.03 mmol) was added via syringe. Copper()) iodide (1.9 mg, 0.01 mmol), dichloro(bisbenzonitrile)palladium (5.7 mg, 0.015 mmol) and diisopropylamine (84 muL, 0.60 mmol) were added. The traces of the air were removed and the mixture was stirred under nitrogen at ambient temperature overnight. The mixture was diluted with ethyl acetate (10 mL) and filtered through a short path of silica gel. The filtrate was concentrated and purified by column chromatography (silica gel Fluka 60, hexanes/ethyl acetate 7:3 -1: 1 – 3: 7) yielding ethyl [4-[3,5-bis-(3-methoxyphenylethynyl)- phenylsulfanyl]-2-methylphenoxy]acetate. Yield: 87 mg (62 %). RF (Si02, hexanes/ethyl acetate 9:1) 0.25. , ¹H NMR spectrum (200 MHz, CDCI3, No.H) : 7.48 (t, J=1.4 Hz, 1 H) ; 7.35-7.25 (m, 6 H); 7.15- 7.01 (m, 4 H) ; 6.95-6.85 (m, 2 H) ; 6.72 (d, J=8.5 Hz, 1 H) ; 4.67 (s, 2 H) ; 4.27 (q, J=7.1 Hz, 2 H) ; 2.30 (s, 3 H); 1.29 (t, J=7.1 Hz, 3 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, 3-Ethynylanisole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVO NORDISK A/S; WO2005/105726; (2005); A1;,
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Some common heterocyclic compound, 148583-65-7, name is 4-Fluoro-2-isopropoxyaniline, molecular formula is C9H12FNO, 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. Product Details of 148583-65-7

A mixture of 7-chlorothiazole[5,4-d]pyrimidine (50 mg, 0.292 mmol), toluene-4-sulfonicacid (6 mg, 0032 mmol), 4-fluoroisopropoxyaniline (49 mg, 0.290 mmol) and IPA (2m1)were sealed in a microwave reactor vial and irradiated at 170C for 15 minutes in theBiotage 1-60 microwave reactor. The reaction mixture was concentrated and theresidue taken up in 20% MeOH in DCM and passed through an aminopropyl cartridge.The product was recovered by washing through with 20% MeOH in DCM. The solutionwas concentrated and the crude product purified by flash column chromatographyeluting with 10-20% EtOAc in petroleum ether to give a pale pink solid (52 mg, 58%).1H NMR (400 MHz, CHLOROFORM-d) 5 1.44 (d, J=5.95 Hz, 6H), 4.56-4.64 (m, IH),6.69-6.77 (m, 2H), 8.58-8.62 (m, IH), 8.64-8.65 (m, 1H), 8.67-8.72 (m, IH), 8.88 (s,1 H); m/z (ES+APCI) :304 [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 148583-65-7, its application will become more common.

Reference:
Patent; MEDICAL RESEARCH COUNCIL TECHNOLOGY; WINTER-HOLT, Jon James; MCIVER, Edward Giles; AMBLER, Martin; LEWIS, Stephen; OSBORNE, Joanne; WEBB-SMITH, Kayleigh; (257 pag.)WO2017/85484; (2017); 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. 1515-95-3, name is 1-Ethyl-4-methoxybenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 1515-95-3

Dissolve 2-methylethylbenzene (1.0 mmol), iron complex 1 (0.02 mmol) and H2O2 (1.5 mmol) in 2 mL of methanol and react at room temperature for 8 hours.After the reaction, the concentrated reaction solution was directly separated by silica gel column chromatography and dried to the same quality.The corresponding product C9H12O was obtained (93% yield).

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; Shanghai Institute of Technology; Yao Zijian; Qiao Xinchao; Zhu Jingwei; Lin Nan; (13 pag.)CN110627841; (2019); A;,
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