Month: February 2021

Related Products of 38197-43-2, 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 38197-43-2 as follows.

To a solution of 2-bromo-1-methoxy-3-methylbenzene (Combi-Blocks CAS No.38197-43-2) (1.024 g, 5.09 mmol) in tetrahydrofuran (25.5 mL) was added bis(dibenzylideneacetone)palladium (0.059 g, 0.102 mmol) and Q-Phos (1,2,3,4,5-Pentaphenyl-1′-(di-tert-butylphosphino)ferrocene) (pentaphenyl(di-tert-butylphosphino)ferrocene, 0.072 g, 0.102 mmol). Nitrogen was bubbled through the solution for about 3 minutes, then a 0.4 M in tetrahydrofuran solution of (1-(methoxycarbonyl)cyclopropyl)zinc(II) bromide (25.5 mL, 10.19 mmol) was added dropwise over 5 minutes and the internal temperature rose from 23.5 C. to 24.8 C. The reaction was stirred for 15 hours at ambient temperature, at which point it was quenched with saturated aqueous ammonium chloride (30 mL), diluted with methyl tert-butyl ether (130 mL), and the layers were separated. The organic layer was filtered through a pad of silica gel. The filtrate was concentrated in vacuo to give a crude residue that was purified via flash chromatography, eluting on a 40 g silica gel cartridge with 1-40% ethyl acetate/heptanes over 40 minutes to provide the title compound. 1H NMR (400 MHz, CDCl3) delta ppm 7.15 (t, J=7.9 Hz, 1H), 6.76-6.80 (m, 1H), 6.73 (d, J=8.2 Hz, 1H), 3.80 (s, 3H), 3.60 (s, 3H), 2.32 (s, 3H), 1.71-1.75 (m, 2H), 1.54 (s, 2H)+ MS (ESI+) m/z 221 (M+H)+, 243 (M+Na)+.

According to the analysis of related databases, 38197-43-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Couty, Sylvain; Desroy, Nicolas; Gfesser, Gregory A.; Housseman, Christopher Gaetan; Kym, Philip R.; Liu, Bo; Mai, Thi Thu Trang; Malagu, Karine Fabienne; Merayo Merayo, Nuria; Picolet, Olivier Laurent; Pizzonero, Mathieu Rafael; Searle, Xenia B.; Van der Plas, Steven Emiel; Wang, Xueqing; Yeung, Ming C.; (189 pag.)US2019/77784; (2019); A1;,
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These common heterocyclic compound, 321-28-8, name is 1-Fluoro-2-methoxybenzene, 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: 1-Fluoro-2-methoxybenzene

Step 1. Preparation of 1-(3-fluoro-4-methoxyphenyl)-2-phenyl-ethan-1-one. Aluminum chloride (42.17 g, 316 mmol) and dichloromethane (350 mL) were cooled to 2 C. and phenylacetylchloride (40.50 g, 262 mmol) in dichloromethane (30 mL) was added. 2-Fluoroanisole (32.77 g, 260 mmol) in dichloromethane (30 mL) was added. The cooling bath was removed, and the mixture was stirred for 1 hour. The reaction mixture was poured into concentrated HCl (150 mL), filtered through diatomaceous earth, washed with saturated aqueous NaHCO3, dried over MgSO4, and concentrated. A white solid was obtained by crystallization from dichloromethane/hexane (29.2 g, 46%): mp 105-106 C.

The synthetic route of 1-Fluoro-2-methoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; G. D. Searle & Co.; US5859257; (1999); A;,
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These common heterocyclic compound, 349-65-5, name is 2-Methoxy-5-(trifluoromethyl)aniline, 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. HPLC of Formula: C8H8F3NO

2-Methoxy-5 (trifluoromethyl) aniline (commercially available) (109.7 mg, 0.551 mmol) was dissolved in 14 mL dichloromethane. Saturated aqueous [NAHCO3] solution (14 mL) was added and the mixture was cooled to [0 C.] While stirring, the mixture was treated with phosgene by addition to the organic layer via syringe in one portion (0.95 mL, 1.92 mmol). The mixture was then stirred vigorously for 0.5 h, then the layers were separated. The aqueous layer was extracted once with dichloromethane and the combined organics were dried [(MGS04),] filtered and the dichloromethane was removed in vacuo. The isocyanate residue was added to the aminonaphthyl pyrimidine ether (186 mg, 0.551 mmol) in 2 mL anhydrous THF. The reaction mixture was left stirring at room temperature overnight and then concentrated in vacuo and triturated with ether to provide 250 mg of a pink solid. The product was purified by column chromatography on silica gel, eluting with 1: 9: 90 [NH40H] : MeOH: [CH2CL2] to provide 110 mg of the title compound as a tan foam.

The synthetic route of 2-Methoxy-5-(trifluoromethyl)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM PHARMACEUTICALS, INC.; WO2004/14870; (2004); A1;,
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Reference of 1535-73-5, A common heterocyclic compound, 1535-73-5, name is 3-Trifluoromethoxyaniline, molecular formula is C7H6F3NO, 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 mixture of compound 3B-1 (2.00 g, 8.98 mmol, 1.0 eq) and compound 3D-1 (1.91 g, 10.8 mmol, 1.2 eq) in isopropanol (20 mL) was added TFA (1.02 g, 8.98 mmol, 1.0 eq) in one portion at 20 ¡ãC under nitrogen. The mixture was stirred at 90 ¡ãC for 18 hours. LC-MS (ET15060-21-P1A1) showed the reaction was completed. The resulting suspension was cooled, and the product was filtered off, washing with a small volume of dichloromethane (10 mL) to give compound 3D-2 (3.00 g, 8.26 mmol, 91.9 percent yield) as yellow solid which was used for next step directly. ln NMR: ET15060-21-P1A1 400 MHz DMSO-d6 9.68 (s, 1H), 8.71 (d, J = 8.8 Hz, 1H), 8.15 (d, J = 6.0 Hz, 1H), 8.03 (s, 1H), 7.91 (dd, J = 8.4, 1.2 Hz, 1H), 7.71 (d, J = 8.4, Hz, 1H), 7.45 (t, J = 8.4 Hz, 1H), 6.98 (d, J = 8.0 Hz, 1H), 6.90 (d, J = 6.0 Hz, 1H), 2.48 (s, 3H).

The synthetic route of 1535-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LUTRIS PHARMA LTD.; SHELACH, Noa; (76 pag.)WO2019/26065; (2019); A2;,
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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. 366-99-4, name is 3-Fluoro-4-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 3-Fluoro-4-methoxyaniline

Step 2. To a solution of l-(6-chloropyrazin-2-yl)-2-methyl-lH-benzo[d]imidazole (96 mg, 0.36 mmol) and 3-fluoro-4-methoxyaniline (71 mg, 0.5 mmol) in THF (1 mL) at room temperature was added KOt-Bu (1M in THF, 1 mL, 1 mmol). The mixture was reacted for 5 minutes, then the reaction was quenched with AcOH and the product partitioned between ethyl acetate and aqueous ammonium chloride. The organic layer was dried, concentrated and purified by chromatography on silica gel (gradient from ethyl acetate:hexane 1:2 to ethyl acetate: methanol 5: 1). The fractions were concentrated and the residue was washed with an ethyl acetate: ether mixture, then filtered and dried to provide the title compound as a yellow/brown solid (39 mg, 25 percent). ]H NMR (DMSO-i delta 9.93 (s, 1H), 8.31 (s, 1H), 8.25 (s, 1H), 7.61 – 7.68 (m, 2H), 7.51 – 7.55 (m, 1H), 7.32 – 7.36 (m, 1H), 7.26 – 7.26 (m, 1H), 7.23 – 7.30 (m, 2H), 7.14 (t, J = 9.1 Hz, 1H), 3.79 (s, 3H), 2.63 (s, 3H); MS m/z 350 (ESI) [M+H]+.

According to the analysis of related databases, 366-99-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PTC THERAPEUTICS, INC.; BAIAZITOV, Ramil; CHOI, Soongyu; DU, Wu; HWANG, Seongwoo; LEE, Chang-Sun; LIU, Ronggang; MOON, Young-Choon; PAGET, Steven, D.; REN, Hongyu; SYDORENKO, Nadiya; WILDE, Richard, Gerald; WO2015/76800; (2015); A1;,
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Reference of 538-86-3, 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. 538-86-3 name is (Methoxymethyl)benzene, 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.

General procedure: A mixture of nitriles (5 mmol), methyl ethers (6 mmol) and Fe(ClO4)3¡¤H2O (5percentmol) was placed in a round bottom flask. Then the reaction mixture was heated at 100 ¡ãC for the given time. After completion of the reaction monitored by thin layer chromatography (TLC), 10 ml water was added into reaction system and extracted with ethyl acetate (3 ¡Á 20 ml). The organic layers were collected, combined, washed with water (3 ¡Á 20 ml), dried over anhydrous Na2SO4, and concentrated under vacuum. The pure products (1a?1k and 2a?2p) were obtained by directly passing through a silica gel (200?300 mesh) column using petroleum ether/ethyl acetate (10:1?5:1).

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

Reference:
Article; Yin, Guibo; Yan, Bin; Chen, Junqing; Ji, Min; Journal of the Iranian Chemical Society; vol. 16; 6; (2019); p. 1355 – 1363;,
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Reference of 332-48-9,Some common heterocyclic compound, 332-48-9, name is 1-(2-Bromoethoxy)-4-fluorobenzene, molecular formula is C8H8BrFO, 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 solution of diethyl but-3-en-1-ylmalonate (2.00 g, 9.3 mmol) in DMF was added NaH (448.0 mg, 11.2 mmol) at 0 C. The mixture was stirred at 0 C for 30 min. Then 1- (2- bromoethoxy) -4-fluorobenzene was added and the mixture was stirred at room temperature for 10.5 hr. The reaction mixture was quenched with water and the mixture was extracted with AcOEt. The organic layer was dried over Na2S04, filtered and evaporated. The crude product was purified by silica gel column chromatography (hexane: AcOEt = 200: 1 to 20: 1) to give the titled compound (2.2 g). ‘H NMR (CDC13) 8 : 7.00-6. 90 (m, 2H), 6.80-6. 76 (m, 2H), 5. 85-5. 67 (m, 1H), 5.07-4. 96 (m, 2H), 4.30-4. 20 (m, 4H), 4.05-3. 95 (m, 2H), 2.45-2. 40 (m, 2H), 2.15-1. 92 (m, 4H), 1.29-1. 15 (m, 6H) ppm.

The synthetic route of 332-48-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER JAPAN, INC.; PFIZER INC.; WO2005/80317; (2005); A2;,
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Synthetic Route of 54149-17-6, 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. 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

According to the literature [39], we followed the N-alkylation reaction to carry out the synthesis of compound 3. A 100mL round bottom flask was charged with intermediate 2 (1mmol), 1-bromo-2-(2-methoxyethoxy)ethane (2.2mmol) and sodium hydroxide (4mmol) in acetonitrile (15mL). The reaction mixture was stirred at 80C overnight. After removing the solvent, the residue was dissolved in dichloromethane. The organic solution was washed with water three times and then dried over anhydrous magnesium sulfate. Purified by column chromatography on silica gel with gradient eluents of petroleum ether and ethyl acetate, the pure target compound 3 was afforded.

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-methoxyethoxy)ethane, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Jiang, Kai; Chen, Si-Hong; Luo, Shi-He; Pang, Chu-Ming; Wu, Xin-Yan; Wang, Zhao-Yang; Dyes and Pigments; vol. 167; (2019); p. 164 – 173;,
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Application of 89282-70-2,Some common heterocyclic compound, 89282-70-2, name is 2-Methoxy-2-methylpropan-1-amine, molecular formula is C5H13NO, 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 5 N-(3-{[(2-methoxy-2-methylpropyl)amino]methyl}-8-methylquinolin-7-yl)-4-(tetrahydrofuran-2-ylmethoxy)benzamide monohydrochloride [Show Image] N-(3-Formyl-8-methylquinolin-7-yl)-4-(tetrahydrofuran-2-ylmethoxy)benzamide (1.0 g) obtained in Reference Example 2 and 2-methoxy-2-methylpropan-1-amine 0.5 oxalate (600 mg) were suspended in 1-methyl-2-pyrrolidone (10 mL) and acetic acid (5.0 mL) and the mixture was stirred at room temperature for 3 hr. Sodium triacetoxyborohydride (2.35 g) was added and the mixture was stirred at room temperature for 3 hr. 1N Aqueous sodium hydroxide solution was added to quench the reaction and basify the mixture. The mixture was partitioned and extracted with ethyl acetate, the organic layer was added to a solution of citric acid (4.0 g) in water (40 mL)-dimethyl sulfoxide (20 mL), and the mixture was washed with ethyl acetate. 1N Aqueous sodium hydroxide solution was added to the aqueous layer, and the mixture was partitioned and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained amorphous product was dissolved in ethyl acetate, and 4N hydrogen chloride-ethyl acetate solution (0.15 mL) was added. The obtained solid was recrystallized from ethyl acetate-methanol to give the title compound (101 mg, yield 8%) as a colorless solid. 1H NMR (300 MHz, DMSO-d6) delta: 1.20 (6 H, s), 1.68 – 1.72 (1 H, m), 1.87 – 1.90 (2 H, m), 1.96 – 2.00 (2 H, m), 2.68 (3 H, s), 2.97 – 3.00 (1 H, m), 3.11 (3 H, s), 3.68 – 3.81 (2 H, m), 4.02 – 4.06 (2 H, m), 4.16 – 4.20 (1 H, m), 4.42 (2 H, s), 7.09 (2 H, d, J=8.7 Hz), 7.75 (1 H, d, J=8.7 Hz), 7.90 (1 H, d, J=8.7 Hz), 8.04 (2 H, d, J=8.7 Hz), 8.72 (1 H, s), 9.20 (1 H, s), 9.27 (2 H, br), 10.25 (1 H, s).

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

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2392573; (2011); 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. 5467-58-3, name is 1-Bromo-4-methoxynaphthalene, A new synthetic method of this compound is introduced below., SDS of cas: 5467-58-3

5-a. Synthesis of 1-methoxy-4-{3,5-(diphenyl)phenyl}naphthalene 1-Methoxy-4-{3,5-(diphenyl)phenyl}naphthalene was synthesized as follows. 1-Bromo-4-methoxynaphthalene (25 g, 0.105 mol), 3,5-diphenylphenylboronic acid 37.6 g (0.137 mol), potassium carbonate (21.9 g, 0.16 mol), tetrakis(triphenylphosphine)palladium(0) (2.4 g, 0.01 mol), water (25 mL), tetrahydrofuran (75 mL) and toluene (75 mL) were stirred in a 250 mL round-bottom flask for 12 hours under reflux. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with ethyl acetate (500 mL) and water (600 mL). The organic layer was dried with magnesium sulfate and concentrated under reduced pressure. The resulting solid was dissolved in hot toluene (1000 mL) and filtered. The filtrate was concentrated and recrystallized in methanol (800 mL). The resulting solid was filtered and washed with hexane (300 mL) to obtain a product (23.5 g, 0.061 mol, 57.6%).

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; SFC CO., LTD.; US2011/108827; (2011); A1;,
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