Month: May 2021

Adding a certain compound to certain chemical reactions, such as: 589-10-6, name is (2-Bromoethoxy)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 589-10-6, name: (2-Bromoethoxy)benzene

Compound 99 (100 mg, 0.371 mmol) to DCM (2 mL) the solution was dissolved in methyl isothiocyanate (30.0 , 0.446 mmol) was slowly added dropwise in a 0 and then, at room temperature two hours then stirred dongan. After checking the completion of the reaction by TLC, the solution was diluted with DCM and extracted with brine. The organic layer was dried over anhydrous Na2SO4, concentrated and filtered. The concentrated filtrate was purified by column chromatography (Hex: EtOAc = 1: 2) to give Compound 101 was synthesized via a (69.3 mg, 55%, colorless oil).

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

Reference:
Patent; Korea Institute of Science and Technology; Ulsan University Academic Cooperation; Kim, Dong Jin; Nam, Gil Soo; Choe, Gyung Ir; Park, Woong Saw; Kim, Young Soo; Pyeon, Sung Lim; Hwang, Hyun Suk; Mun, Doo Hyun; Hwang, Ohn Yu; Sim, Young Sun; Kim, Jin Woo; Kim, Yun Gyung; Kang, Yong Gu; Park, Gi Tuk; (106 pag.)KR101525019; (2015); B1;,
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Reference of 4316-51-2, A common heterocyclic compound, 4316-51-2, name is 4-Methoxytriphenylamine, molecular formula is C19H17NO, 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.

(1) Synthesis of 4,4′-Diformyl-4″-methoxytriphenylamine (8c) Reactions were conducted in the same manner as in (4) in Example 2 except that 20.0 g (0.075 mol) of 4-methoxytriphenylamine (7c) was used in place of triphenylamine (7a). Thus, 19.0 g of 4,4′-diformyl-4″-methoxytriphenylamine (8c) was obtained. Theoretical yield, 76.5%; m.p., 113-114 C. Spectral data for this compound are as follows. 1 H-NMR spectrum (400 MHz, CDCl3, deltappm): 3.85 (3H, s), 6.94 (2H, d, J=9.0 Hz), 7.12 (2H, d, J=9.0 Hz), 7.17 (4H, d, J=8.7 Hz), 7.56 (4H, d, J=8.7 Hz), 9.88 (2H, s)

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; Takasago International Corporation; US5573878; (1996); A;,
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Electric Literature of 37466-89-0, These common heterocyclic compound, 37466-89-0, name is 3-Methoxybenzene-1,2-diamine, 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.

The reaction mixture of 3-methoxy-o-phenylenediamine (2, 190mg, 1.37mmol)and HCOOH (5mL) was refluxed for 4h, then cooled to room temperature and poured into ice/ water (20mL). The mixture was treated with 10% NaOH aqueous solution to pH?8 and then extracted with ethyl ether (15mL×3). The combined extracts were washed with water and brine, then dried over anhydrous MgSO4. The organic phase was concentrated to give the crude product, which was purified by column chromatography with CH2Cl2-MeOH (v/v=60/1). The desired product 4-methoxy-1H-benzo[d]imidazole (162mg) was afforded as white powder with 83.9% yield. M.p. 165-167C; 1H NMR (acetone-d6, 300MHz, delta ppm): 8.08 (1H, s), 7.21 (1H, d, J=7.8Hz), 7.11 (1H, t, J=7.8Hz), 6.73 (1H, d, J=7.8Hz), 3.97 (3H, s); HRMS (ESI): m/z, calcd. For C8H9N2O [M+H]+ 149.0709 found 149.0707.

The synthetic route of 37466-89-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhou, Jie; Jin, Jing; Zhang, Yi; Yin, Yuwen; Chen, Xiaoguang; Xu, Bailing; European Journal of Medicinal Chemistry; vol. 68; (2013); p. 222 – 232;,
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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. 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine, A new synthetic method of this compound is introduced below., Safety of (4-(Trifluoromethoxy)phenyl)methanamine

A mixture of. (S) -7-hydroxy-5,6, 7, 8-tetrahydro-naphthalen-1-yl)-carbamic acid phenyl ester (85.0 mg, 0.30 mmol) and 4-trifluoromethoxy-benzylamine (57.4 mg,. 0.30 mmol) in DMSO (1.0 ml) was stirred at 150 &degC for 1.5 hours. The reaction mixture was cooled to room temperature, and ethylacetate and water were added. The extracted organic layer was washed with water then brine, dried over Na2S04, filtered and concentrated under reduced pressure. The obtained residue was triturated with dichloromethane and hexane to obtain N-{(S)-7-hydroxy-5, 6,7, 8-tetrahydro- naphthalen-l-yl}-N’- (4-trifluoromethoxy-benzyl)-urea (95.0 mg, 83 % yield). 1H NMR (DMSO-d6) 5 1. 54-1. 65 (m, 1H), 1.81-1. 92 (m, 1H), 2.25-2. 38 (m, 1H), 2.68-2. 88 (m, 3H), 3. 86-3. 98 (m, 1H), 4.32 (d, J= 6.0 Hz, 2H), 4.85 (d, J= 4.1 Hz, 1H), 6.72 (d, J= 7. 5 Hz, 1H), 6.98 (t, J= 7.5 Hz, 1H), 7.06 (t, J= 6.0 Hz, 1H), 7.34 (d, J= 8.3 Hz, 2H), 7.43 (d, J= 8.3 Hz, 2H), 7.63 (d, J= 7.5 Hz, 1H), 7.5 (s, 1H). Molecular weight : 380. 36 MS (M+H) : 381 In vitro activity class: A Chiral HPLC (ChiralCel AD 0.49 cm x 25 cm column, n-hexane/ethanol-= 90/10, flow rate 1.5 mL/min) S-isomer was detected at 13.2 minutes.

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; BAYER AKTIENGESELLSCHAFT; WO2003/95420; (2003); A1;,
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Synthetic Route of 6298-96-0, A common heterocyclic compound, 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, molecular formula is C9H13NO, 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.

EXAMPLE 1.4(S)-N-(1-(4-methoxyphenyl)ethyl)-2-(1-methyl-3-phenyl-4-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-6-yloxy)acetamide A solution of (1-Methyl-3-phenyl-4-trifluoromethyl-1H-pyrazolo[3,4-b]pyridin-6-yloxy)-acetic acid (350 mg, 0.996 mmol), DIC (189 mg, 1.494 mmol) and HOBt (175 mg, 1.295 mmol) in DMF (10 ml) was stirred at rt for 10 min. (S)-(-)-4-methoxy-alpha-methyl benzyl amine (166 mg, 1.096 mmol) was added to the reaction mixture at rt and stirring was continued for 12 h at rt. After completion of the reaction, the reaction mixture was poured into rapidly stirred ice-cold water to obtain the crude product as a solid. The solid was collected by filtration and dried under vacuum. The product was further purified by flash column chromatography [(eluent: EtOAc/hexane (1:3)] to yield the title compound as a white solid (305 mg, 63%). [1H-NMR (CDCl3, 300 MHz) delta 7.58-7.39 (m, 5H), 7.32-7.21 (m, 2H), 6.99 (s, 1H), 6.85 (d, 2H), 6.51 (d, 1H), 5.31-5.22 (m, 1H), 5.0 (s, 2H), 4.05 (s, 3H), 3.8 (s, 3H), 1.52 (d, 3H); HPLC RtB=5.933 min. (98%); LCMS RtA=1.785, [M+H]+=485.1; Mp=172-174 C.]

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; NOVARTIS AG; US2012/258973; (2012); A1;,
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Electric Literature of 53087-13-1,Some common heterocyclic compound, 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, molecular formula is C13H11BrO, 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: All glassware used in the following procedure was flame dried and then cooled under nitrogen prior to use. A portion (1 mmol) of the required aryl bromide (10.00 mmol) was added to a suspension of magnesium turnings (250 mg, 10.5 mmol) in tetrahydrofuran (12 mL) containing a few iodine crystals and the mixture gently heated whilst stirring vigorously. Once the reaction forming the Grignard reagent had initiated (reflux became self-sustaining) the remaining bromobenzene was added dropwise at such a rate that gentle reflux was maintained. The mixture was then heated at reflux until the magnesium was consumed (usually 30-60 min) and then was cooled for 30 min using an ice bath. A solution of 1-benzyl 4-piperidone (5.00 – 6.25 mmol) in tetrahydrofuran (8 mL) was added dropwise over 1-2 h and the mixture was stirred for 1 h and then the ice bath was removed and the reaction mixture allowed to warm to room temperature whilst stirring for at least a further 2 h. The reaction was quenched by the addition of saturated ammonium chloride solution (60 mL) and extracted into diethyl ether (2 × 30 mL) followed by ethyl acetate (3 × 30 mL). The organic phases were combined and subjected to standard work up conditions to give the required crude product. Purification of the title compound was achieved by flash chromatography on silica or, where indicated, by elution through a short length silica column using the eluant specified. In some cases, the crude piperidinol was dehydrated directly without purification as indicated.

The synthetic route of 53087-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Conway, Richard J.; Valant, Celine; Christopoulos, Arthur; Robertson, Alan D.; Capuano, Ben; Crosby, Ian T.; Bioorganic and Medicinal Chemistry Letters; vol. 22; 7; (2012); p. 2560 – 2564;,
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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. 64465-53-8, name is 4-Fluoro-3-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H8FNO

Description 34; 5-[(4-Fluoro-3-methoxvphenvl) aminolmethvlene}-2, 2-dimethvl- 1 3-dioxane-4, 6-dione; To a stirred solution of 4-fluoro-3-methoxyaniline (20 g, 142 mmol) in acetonitrile (200 ml) was added 2, 2-dimethyl-1, 3-dioxane-4,6-dione (Meldrum’s acid) (22.5 g, 156 mmol) followed by trimethyl orthoformate (18.6 ml, 170 mmol). The mixture was heated to reflux for 3 hours. The cooled mixture was filtered to give the title compound (30.9 g, 74%). 1H NMR (400 MHz, CDCl3) 1.76 (6 H, s), 3.94 (3 H, s), 6.76-6. 83 (2 H, m), 7.14 (1 H, dd, J10. 5 and 8.4), 8.56 (1 H, d, J14. 4), 11.23 (1 H, d, J14.4).

According to the analysis of related databases, 64465-53-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2005/47279; (2005); A1;,
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Electric Literature of 115144-40-6, These common heterocyclic compound, 115144-40-6, name is 3,4-Difluoroanisole, 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.

a) 7.29 ml (66.3 mmol) of titanium tetrachloride were added while stirring to a solution, cooled to 0, of 5.73 g (39.8 mmol) of 3,4-difluoroanisole in 30 ml of anhydrous dichloromethane. Subsequently, the mixture was treated dropwise over 10 minutes with 3.51 ml (39.6 mmol) of 1,1-dichloromethyl methyl ketone and stirred at room temperature for one hour. The mixture was poured into 100 ml of ice-water, extracted twice with 150 ml of dichloromethane each time and the combined organic phases were washed once with 100 ml of water and once with 100 ml of saturated sodium chloride solution. After drying over magnesium sulphate concentration was carried out in a vacuum. The crude product obtained was purified by column chromatography on silica gel (hexane/ethyl acetate 4:1). There were obtained 5.8 g (84%) of 4,5-difluoro-2-methoxybenzaldehyde as a white solid with m.p. 74.

Statistics shows that 3,4-Difluoroanisole is playing an increasingly important role. we look forward to future research findings about 115144-40-6.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; EP906301; (2002); B1;,
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Synthetic Route of 5414-19-7, The chemical industry reduces the impact on the environment during synthesis 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, I believe this compound will play a more active role in future production and life.

Under argon, 100 mg (0.30 mmol) of (4S)-1-(4-aminophenyl)-8-methoxy-N,4-dimethyl-4,5-dihydro-3H-2,3-benzodiazepine-3-carboxamide (Example 53.2A) were dissolved in 4 ml of N,N-dimethylacetamide, and 103 mg (0.44 mmol) of 1-bromo-2-(2-bromoethoxyl)ethane and 0.1 ml (0.59 mmol) of diisopropylethylamine were added. The mixture was stirred at 120 C. for three days. The reaction was added to water and extracted three times with ethyl acetate. The solvent was removed on a rotary evaporator and the residue was purified by flash chromatography. This gave 95 mg (79% of theory) of the desired product.

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-Bromo-2-(2-bromoethoxy)ethane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SIEGEL, STEPHAN; BAURLE, STEFAN; CLEVE, ARWED; HAENDLER, BERNARD; FERNANDEZ-MONTALVAN, AMAURY ERNESTO; MONNING, URSULA; KRAUSE, SABINE; LEJEUNE, PASCALE; SCHMEES, NORBERT; BUSEMANN, MATTHIAS; HOLTON, SIMON; KUHNKE, JOACHIM; (434 pag.)JP2015/529192; (2015); A;,
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Electric Literature of 6358-77-6,Some common heterocyclic compound, 6358-77-6, name is 5-Bromo-2-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.

General procedure: A mixture of sydnone (1 eq.), aryl halide (1.5 eq.), palladium acetate (5mol %), XPhos (10mol%) and potassium carbonate (2 eq.) in DMF (0.5 M) under an atmosphere of nitrogen was heated at 80 C (for 3-alkylsydnones) or 120 C (for 3-arylsydnones) for 14 h before the reaction was allowed to cool to r.t. and water was added. The resulting mixture was extracted with ethyl acetate:40-60 petroleum ether (9:1) and the combined organic layers dried over MgSO4 and concentrated in vacuo. Flash silica chromatography (eluting solvent 20%-100% ethyl acetate in 40-60 petroleum ether) afforded the target 3,4-diarylsydnones. The compounds could be further purified by recrystallisation from ethanol or dichloromethane/petrol.

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-2-methoxyaniline, its application will become more common.

Reference:
Article; Brown; Harrity; Tetrahedron; vol. 73; 22; (2017); p. 3160 – 3172;,
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