Month: June 2021

Synthetic Route of 105404-89-5, 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. 105404-89-5, name is 2,7-Dibromo-3,6-dimethoxynaphthalene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of 2,7-dibromonaphthalene (300 mg, 1.05 mmol) in1,4-dioxane (10 mL) were added 4-nitrophenylboronic acid (381 mg, 2.28 mmol), Pd(PPh3)4 (28 mg, 0.024 mmol), and aq. Cs2CO3 (2 M, 2 mL), and the reaction mixture was stirred overnight at reflux under Ar. Then, the reaction mixture was diluted with water (30 mL), and the product was extracted with chloroform (100 mL × 3). The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography [hexane/chloroform (2:1)] to give 2,7-bis(4-nitrophenyl)naphthalene 3a (326 mg, 0.879 mmol, 84%) as a yellow solid

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, 2,7-Dibromo-3,6-dimethoxynaphthalene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hachiya, Sojiro; Asai, Kengo; Konishi, Gen-Ichi; Tetrahedron Letters; vol. 54; 14; (2013); p. 1839 – 1841;,
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Reference of 768-70-7, A common heterocyclic compound, 768-70-7, name is 3-Ethynylanisole, molecular formula is C9H8O, 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: General produce: o-iodophenol (0.5 mmol), alkyne (1.0 mmol) andbase (1.0 mmol) were added into a 10 mL dry Schlenk tube under Ar,then anhydrous DMF (5 mL) was injected into the mixture using syringe.Then the solution stirred at preheated oil bath (160 C). The reactionwas monitored by TLC and GC.The mixture was cooled down toroom temperature after full conversion, then diluted with dichloromethaneand washed with water three times. The organic layerwas separated and washed with brine followed by drying with anhydrousNa2SO4. The filtrate was concentrated in vacuo to afford thecrude product, which was purified by flash column chromatography onsilica gel (petroleum ether).

The synthetic route of 768-70-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ji, Guijie; Duan, Yanan; Zhang, Shaochun; Yang, Yong; Catalysis Today; (2019); p. 101 – 108;,
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Synthetic Route of 61367-43-9, 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. 61367-43-9, name is cis-4-Methoxycyclohexanamine hydrochloride belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 284 6-(4-(4-cyano-2-fluorophenyl)-5-hydroxy-lH-pyrazol-l-yl)-N- ((ls,4s)-4-methoxycyclohexyl)nicotinamide [01159] [01160] Combined EDC (1 15 mg, 0.601 mmol), HOBT (27.1 mg, 0.200 mmol), (cis)-4- methoxycyclohexanamine hydrochloride (66.4 mg, 0.401 mmol) and 6-(4-(4-cyano-2- fluorophenyl)-5 -hydroxy- lH-pyrazol-l-yl)nicotinic acid (65 mg, 0.200 mmol) in DMF (0.8 mL) and then added DIPEA (0.175 mL, 1.002 mmol). After 24 hours, the reaction mixture was purified by preparative HPLC (ACN/water with formic acid) to give the title compound (23 mg, 0.053 mmol, 26.3 %) as a tan solid. MS: 436 (M+H). NMR (400 MHz, DMSO- de) 5 ppm 1.34 – 1.48 (m, 2 H) 1.49 – 1.65 (m, 4 H) 1.76 – 1.88 (m, 2 H) 3.17 (s, 3 H) 3.31 (br. s., 1 H) 3.73 – 3.87 (m, 1 H) 7.62 (dd, J=8.2, 1.6 Hz, 1 H) 7.77 (dd, J=1 1.7, 1.6 Hz, 1 H) 8.16 (d, J=3.0 Hz, 1 H) 8.31 – 8.44 (m, 3 H) 8.55 (t, J=8.0 Hz, 1 H) 8.84 (dd, J=2.0, 1.0 Hz, 1 H) 13.71 (br. s., 1 H).

The synthetic route of cis-4-Methoxycyclohexanamine hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; BROWN, Jason, W.; DAVIS, Melinda; IVETAC, Anthony; JONES, Benjamin; KIRYANOV, Andre, A.; KUEHLER, Jon; LANIER, Marion; MIURA, Joanne; MURPHY, Sean; WANG, Xiaolun; WO2014/160810; (2014); A1;,
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Reference of 51344-14-0, A common heterocyclic compound, 51344-14-0, name is N,N-Dimethyl-2-(p-tolyloxy)ethanamine, molecular formula is C11H17NO, 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.

To a test tube containing a magnetic bar was added aryl halide (1.0 mmol), Cu2O (14.3 mg, 0.1 mmol), KOH (169 mg, 3.0 mmol), 2-dimethylaminoethanol (0.3 mL, 3.0 mmol), and DMSO/H2O (1.5 mL/0.5 mL). After flushing with argon, the mixture was stirred in a preheated oil bath at 100 C for 24 h. After cooled to ambient temperature, the reaction mixture was distributed in aqueous HCl (5 %) and ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous MgSO4, and concentrated under vacuum. The crude product was further purified by column chromatography (EtOAc/n-Hexane) to provide the phenols.

The synthetic route of 51344-14-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kim, Jihye; Battsengel, Oyunsaikhan; Liu, Yajun; Chae, Junghyun; Bulletin of the Korean Chemical Society; vol. 36; 12; (2015); p. 2833 – 2840;,
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6346-09-4, name is 4,4-Diethoxybutan-1-amine, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 6346-09-4

Triethylamine (25.6 mL, 185 mmol, 2 eq.) at 0 C was added to a solution of 4-aminobutyraldehyde diethyl acetal (15.0 g, 92.2 mmol, 1.0 eq.) in anhydrous dichloromethane (150 mL) under nitrogen atmosphere, and the reaction mixture was allowed to stir for 15 min, followed by dropwise addition of acetic anhydride (43.9 mL, 464 mmol, 5.0 eq.) at 0 C. The resulting reaction mixture was stirred for 2 h at 40 C. The resulting reaction mixture was quenched with a saturated aqueous solution of Na2CO3 (500 mL) and extracted with dichloromethane (100 mL × 4). The combined organic extract was dried over anhydrous Na2SO4 and concentrated under reduced pressure, yielding the desired compound B, (Fig. 1A, 15.5 g, 82% yield) as colorless oil. The compound was used as such in the next step without further characterization and confirmation.

The synthetic route of 6346-09-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Boutin, Jean A.; Bouillaud, Frederic; Janda, Elzbieta; Gacsalyi, Istvan; Guillaumet, Gerald; Hirsch, Etienne C.; Kane, Daniel A.; Nepveu, Francoise; Reybier, Karine; Dupuis, Philippe; Bertrand, Marc; Chhour, Monivan; Le Diguarher, Thierry; Antoine, Mathias; Brebner, Karen; Da Costa, Herve; Ducrot, Pierre; Giganti, Adeline; Goswami, Vishalgiri; Guedouari, Hala; Michel, Patrick P.; Patel, Aakash; Paysant, Jerome; Stojko, Johann; Viaud-Massuard, Marie-Claude; Ferry, Gilles; Molecular Pharmacology; vol. 95; 3; (2019); p. 269 – 285;,
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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 588-96-5 as follows. Recommanded Product: p-Bromophenetole

Step 1:Magnesium (8.24 g, 0.339 mol) was added to 300 mL of tetrahydrofuran (THF) in a reactor substituted with nitrogen atmosphere and dissolved by stirring. While keeping the internal temperature at 20 to 30 C, 4-bromophenetol 62 g, 0.308 mol) and 220 mL of tetrahydrofuran was slowly added thereto. After completion of the addition, the internal temperature was raised to 40 to 45 C and stirred for 2 hours. Step 2: In a reactor substituted with nitrogen atmosphere, (S)-tert-butyl 2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)aziridine-1-carboxylate (50 g, 0.206 mol) was added to 50 mL of toluene and dissolved with stirring, and CuBrS(CH3)2 (0.4 g, 0.002 mol) was added thereto. The internal temperature was further stirred for 30 minutes while maintaining the internal temperature at 20 to 25 C,and the internal temperature was cooled to -40 C.The solution of 4-bromophenetol magnesium bromide prepared according to the above step 1 was slowly added while keeping the internal temperature at -40 C or lower.After completion of the addition, the internal temperature was raised to -30 to -20 C and stirred for 1 hour. When the reaction was complete, 400 mL of 10% acetic acid aqueous solution and 400 mL of toluene were added to quench and separate.The separated oil layer was washed with 400 mL of a 7% sodium Sodium bicarbonate aqueous solution and 400 mL of purified water, and Sodium sulfate was added to dehydrate and then filtered.Thereafter, the filtrate was concentrated, 150 mL of methanol was added to the concentrated residue, stirred at an internal temperature of 20 to 25 C for 1 hour, and then filtered. The filtrate was concentrated again to give 75.1 g of the title compound tert-butyl (1S)-1-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-(4-ethoxyphenyl)ethylcarbamate yield: 100 %

According to the analysis of related databases, 588-96-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Eseuti Pam Co., Ltd.; Kim Yeong-hun; Oh Jun-hyeon; Kang Sang-gyu; Jang Sun-gi; Im Geun-jo; (14 pag.)KR2018/50091; (2018); A;,
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Related Products of 16618-68-1,Some common heterocyclic compound, 16618-68-1, name is 3-Bromo-5-methoxyaniline, molecular formula is C7H8BrNO, 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.

Step 1 : Synthesis of N-(3-Bromo-5-methoxy-phenyl)acetamideTo a solution of 20 g of 3-bromo-5-methoxy-aniline in 200 mL DCM was added 27.44 mL triethylamine at 0 C .To the reaction mixture was added 7.06 mL acetyl chloride dropwise over 30 min. The reaction was stirred at 30C for 3 h, and then poured onto ice. The pH was adjusted to pH 7 with aqueous NaHC03 and the precipitated solids were removed by filtration. The aqueous was extracted with DCM and the combined organic extracts were dried over sodium sulfate, filtered and evaporated under reduced pressure to yield 20 g N-(3-bromo-5- methoxy-phenyl) acetamide as solid.Analysis: HPLC-MS: Rt = 2.44 min (method Q), M+H = 244 / 246

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; DAHMANN, Georg; HOFFMANN, Matthias; KLICIC, Jasna; LAMB, David James; MCCARTHY, Clive; NAPIER, Spencer; PARRISH, Karen; SCOTT, John; SWANTEK FITZGERALD, Jennifer L.; WALKER, Edward; WO2015/140054; (2015); 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. 157869-15-3, name is 2-((4-Methoxyphenyl)ethynyl)aniline, A new synthetic method of this compound is introduced below., COA of Formula: C15H13NO

General procedure: To a microwave vial, a mixture of 2-alkynylaniline (1 equiv), sulfonyl hydrazide (1.5 equiv), I2 (10 mol%) and pTSA (50 mol%) was taken in 1,4-dioxane irradiated for 15 min at 110C, 100W in CEM microwave synthesizer. The progress and completion of reaction is monitored by TLC using EtOAc/n-Hexane (1:10) as an eluent. The reaction mixture was then cooled to room temperature and extracted with ethyl acetate. The combined organic phase was washed with sodium thiosulphate (50 mL) and dried over Na2SO4. After filtration and evaporation of the solvents in vacuum, the mixture of products was separated by column chromatography on silica gel (EtOAc/n-hexane: 1:10) to yield the desired product 3.

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:
Article; Sharma, Shivani; Pathare, Ramdas S.; Sukanya; Maurya, Antim K.; Goswami, Bhagyashree; Agnihotri, Vijai K.; Sawant, Devesh M.; Pardasani, Ram T.; Tetrahedron Letters; vol. 58; 40; (2017); p. 3823 – 3826;,
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Related Products of 156573-09-0, These common heterocyclic compound, 156573-09-0, name is 1-Bromo-4-ethoxy-2,3-difluorobenzene, 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.

4-Formylphenylboronic acid (s47) (75.9 g),4-bromo-2,3-difluoroethoxybenzene (s48) (100.0 g), potassium phosphate (269.0g), dichlorobistriphenylphosphinepalladium (II) (Pd(Ph3P)2Cl2;8.9 g) and 1,4-dioxane (500 ml) were placed in a reaction vessel under an atmosphere of nitrogen, and the mixture was heated to reflux for 2 hours. After the reaction mixture had been cooled to 25 C, it was treated with water,and the aqueous layer was extracted with toluene. The combined organic layers were washed with water,and then dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by column chromatography with toluene as an eluent and silica gel as a stationary phase powder. The product was purified by recrystallization from a mixed solvent of heptane and toluene (heptane:toluene=l: 1 by volume) to give 4-ethoxy-4′-formyl-2,3-difluoro-l,l’-biphenyl (s49) (102.8g). The yield based on the compound (s48) was 92.9%.

The synthetic route of 156573-09-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JNC CORPORATION; JNC PETROCHEMICAL CORPORATION; KOBAYASHI, MASAHIDE; (87 pag.)JP5849664; (2016); B2;,
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Related Products of 20781-20-8, 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. 20781-20-8 name is (2,4-Dimethoxyphenyl)methanamine, 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 compound 58 (6.6 g, 33.5 mmol) in dichloromethane (100 mE) were added DIPEA (8.65 g, 67 mmol), HOSt (5.4 g, 36.85 mmol) and EDCI (9.6 g, 50.3 mmol). Afier about 15 mm stirring, to the homogeneous reaction mixture was added a solution of 2,4-dimethoxy- benzyl amine (5.6 g, 33.5 mmol) in dichloromethane (50 mE) dropwise under nitrogen atmosphere. The resulting mixture was stirred under nitrogen atmosphere at room temperature for 16 h. The reaction mixture was washed successively with iN NaOH (100 mE), water (100 mE) and brine (100 mE). The organic phase was then dried over Na2SO4 and evaporated to give a crude solid product 59 that crystallized from ethyl ether. Filtration and open air suction drying afforded an off-white solid pure product 9.8 g (96%), (MS: [M+1]=347).

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

Reference:
Patent; AgeneBio, Inc.; Mekonnen, Belew; Butera, John A.; Huang, Jianxing; (331 pag.)US2018/170941; (2018); A1;,
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