Category: ethers-buliding-blocks

Some common heterocyclic compound, 175278-17-8, name is 2-Bromo-4-(trifluoromethoxy)aniline, molecular formula is C7H5BrF3NO, 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. category: ethers-buliding-blocks

According to route (C), 2-bromo-4-trifluoromethoxyaniline (2.3 mL, 15 mmoles, 1 eq.) was placed in l,4-dioxane (55 mL) with Pd(dppf)Cl2.CH2Cl2 (1.2 g, 1.5 mmole, 0.1 eq.). Upon addition of CS2CO3 (19.6 g, 60 mmoles, 4 eq.) and ethylboronic acid (3.3 g, 45 mmoles, 3 eq.), the reaction mixture was heated at l00C and stirred for 14 hours under an inert atmosphere of argon. The reaction mixture was then concentrated under reduced pressure and the resulting residue was purified by column chromatography on silica gel to afford 2-ethyl-4-(trifluoromethoxy)aniline (1.3 g, 42%). (0391) 6.93 (s, 1H), 6.90 (d, J = 8.5 Hz, 1H), 6.63 (d, J = 8.5 Hz, 1H), 3.64 (s, 2H), 2.49 (q, 7 = 7.5 Hz, 2H), 1.25 (t , J= 7.5 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 175278-17-8, its application will become more common.

Reference:
Patent; ABIVAX; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITE DE MONTPELLIER; INSTITUT CURIE; SCHERRER, Didier; TAZI, Jamal; MAHUTEAU-BETZER, Florence; NAJMAN, Romain; SANTO, Julien; APOLIT, Cecile; (0 pag.)WO2020/11810; (2020); A1;,
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Electric Literature of 1535-75-7, These common heterocyclic compound, 1535-75-7, name is 2-(Trifluoromethoxy)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.

General procedure: To a solution of respective anilines (1.0 eq.) in CH2Cl2 (15 mL) was added pyridine at 0 C and the mixture stirred for 5 min. Compound 4 (1.0 eq.) in CH2Cl2 (10 mL) wasadded and the mixture stirred at room temperature for 12-48 h. The mixture was diluted with CH2Cl2 (25 mL) and washed with diluted HCl and water. The organic layer wasdried over anhydrous Na2SO4 and concentrated to obtain crude was subjected to column chromatography on silica gel to yield title compounds 5.

The synthetic route of 1535-75-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Abbavaram, Babul Reddy A.; Reddyvari, Hymavathi R.V.; Journal of the Korean Chemical Society; vol. 57; 6; (2013); p. 731 – 737;,
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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. 7252-83-7, name is 2-Bromo-1,1-dimethoxyethane, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Bromo-1,1-dimethoxyethane

Example 74; (IS, 2R) and (IR, 2S)-2-(4-chlorophenyl)-l’-(2-(4-isopropylpiperazin-l-yl)ethyl)spiro [cyclopropane-l,3′-indolin]-2′-oneSynthesis of (IR, 2S) and (IS, 2R)-2-(4-chlorophenyl)-l’-(2,2- dimethoxyethyl)spiro[cyclopropane-l,3′-indolin]-2′-one; To a solution of (IR, 2S) and (I S, 2R)-2-(4-chlorophenyl)spiro[cyclopropane-l,3′-indolin]- 2′-one (135 mg, 1 mmol) in DMF (1 mL) was added KHMDS (0.5 M in THF, 1.1 mL) was dropwise at room temperature. The mixture was stirred for half an hour before adding bromoacetaldehyde dimethyl acetal (95 mg, 0.55 mmol). The mixture was warmed to 50 C and stirred at that temperature for 2 hours. The mixture was poured into water, extracted with ethyl acetate (3 x 15 mL), dried and concentrated under reduced pressure. Purification by flash column chromatography on silica gel, eluting with hexanes-EtOAc (6: 1 and then 4: 1) gave the desire product as colorless oil (268 mg, 75%). LC/MS m/e calcd. for C2oH2oClN03: 3570, observed (M+H)+: 358.7.

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; F. HOFFMANN-LA ROCHE AG; CHEN, Li; HUANG, Mengwei; FENG, Lichun; HE, Yun; YUN, Hongying; WO2011/69298; (2011); A1;,
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Electric Literature of 162705-07-9,Some common heterocyclic compound, 162705-07-9, name is (Z)-2-Methoxy-5-(3,4,5-trimethoxystyryl)aniline, molecular formula is C18H21NO4, 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: To a solution of substituted benzyl-1H-1,2,3-triazole-4-carboxylic acids (18a-e, 1 mmol) in dry dimethylformamide, EDCI (1.2 mmol) and HOBT (1.2 mmol) were added and the reaction mixture was stirred for 20 min. To the reaction mixture, amino Z-stilbenes (16, 17, 1 mmol) was added and stirred at room temperature for 12 h. The solvent was removed and the residue was dissolved in dichloromethane (50 mL), washed with 5% HCl (2 20 mL), 5% NaHCO3 (2 20 mL), and brine solution (20 mL). The organic layer was separated, dried over anhydrous Na2SO4, filtered, and the solvent was removed to give a crude product which was purified by chromatography (ethyl acetate/hexanes) to givethe desired product (6a-e, 7a-e).

The synthetic route of 162705-07-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kamal, Ahmed; Shaik, Bajee; Nayak, V. Lakshma; Nagaraju, Burri; Kapure, Jeevak Sopanrao; Shaheer Malik; Shaik, Thokhir Basha; Prasad; Bioorganic and Medicinal Chemistry; vol. 22; 19; (2014); p. 5155 – 5167;,
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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. 321-28-8, name is 1-Fluoro-2-methoxybenzene, A new synthetic method of this compound is introduced below., Quality Control of 1-Fluoro-2-methoxybenzene

Initially, 2-fluoroanisole (II) was used to synthesize 3-fluoro-4-methoxyacetophenone (III). AlCl3 (0.6 mol) and acetic anhydride (0.4 mol) were placed in 250 ml of dry dicloromethane. The 2-fluoroanisol (0.2 mol) was added dropwise over a period of 30 minutes to the reaction mixture which was then stirred with a magnetic stir bar for two hours. The reaction was judged complete by TLC. The reaction mixture was then poured in ice and stirred for one hour. The CH2 Cl2 layer was separated and the water layer was extracted twice with CH2 Cl2. Organic layers were combined and washed with 3N HCl and water, dried with MgSO4 and passed through a thick pad of silica. The solvent was rotary evaporated to obtain the crude product, which was crystallized from 7% (v/v) ethyl acetate in hexanes to obtain 70% yield of the crystallized product, 3-fluoro-4-methoxyacetophenone (III).

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; Displaytech, Inc.; US5422037; (1995); A;,
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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. 2525-16-8, name is 7-Methoxy-3,4,5,6-tetrahydro-2H-azepine, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H13NO

To a solution of ethyl N-[3-(3-amidinophenyl)-2-(E)-propenyl]-N-[4-(piperidin-4-yloxy)phenyl]sulfamoylacetate dihydrochloride (0.51 g) obtained in example 59(a) in ethanol (5 ml) were added successively 7-methoxy-3,4,5,6-tetrahydro-2H-azepine (0.34 g) and triethylamine (0.60 ml) at room temperature, and the resulting mixture was stirred at room temperature for 18 hours and then evaporated in vacuo.. The residue obtained was purified by preparative HPLC (YMC-Pack ODS-A; YMC, eluent: 25 % acetonitrile/water).. Subsequently, to a solution of the amorphous solid obtained in ethanol (5 ml) was added a 4N solution of hydrogen chloride in dioxane (1 ml), and the resulting mixture was evaporated to dryness in vacuo.. The residue obtained was dissolved in water and then lyophilized to afford the title compound (0.14 g, yield: 24 %) as a colorless amorphous solid. 1H NMR (400MHz, DMSO-d6) delta ppm: 1.23 (3H, t, J=7.0), 1.46-1.76 (8H, m), 2.01-2.10 (2H, m), 2.86-2.89 (2H, m), 3.45-3.50 (2H, m), 3.57-3.70 (2H, m), 3.85-3.97 (2H, m), 4.20 (2H, q, J=7.0), 4.34 (2H, s), 4.45 (2H, d, J=6.0), 4.70-4.76 (1H, m), 6.45 (1H, dt, J=16.0, 6.0), 6.55 (1H, d, J=16.0), 7.39 (2H, d, J=9.0), 7.54 (2H, d, J=9.0), 7.54 (1H, t, J=8.0Hz), 7.69-7.73 (2H, m), 7.90 (1H, s); IR (KBr, cm-1): 1737, 1674, 1629, 1351, 1158.

According to the analysis of related databases, 2525-16-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sankyo Company, Limited; EP1375482; (2004); A1;,
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Electric Literature of 41789-95-1, 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. 41789-95-1 name is 1-(3-Methoxyphenyl)-N-methylmethanamine, 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 alpha-bromo~2′-acetonaphthone (386.2 g, 1.57 mol) in dichloromethane (2.5 L) at 00C was added compound 3 (249.1 g, 1.65 mol) in 30 min, followed by the addition of triethylamine (220.7 mL, 1.57 mmol) in 45 min. After stirring at 00C for 40 min, the reaction mixture was warmed to room temperature and stirred overnight. The reaction solution was then washed with water (2x) and the aqueous layer was re-extracted with dichloromethane (2x). The combined organic extract was dried over sodium sulfate and concentrated in vacuo. The ketone, compound 4, was obtained as a reddish oil (513.3 g, quantitative), was used in the next step without further purification: ‘H NMR (CDCl3, 500 MHz) 8.50 (s, IH), 8.01(d, J= 8.5 Hz, IH), 7.92 (d, J = 8.0 Hz, IH), 7.88-7.85 (m, 2H)5 7.60-7.54 (m, 2H), 7.26-7.23 (m, IH), 6.97-6.94 (m, 2H), 6.82 (dd, J- 8.0, 2.5 Hz, IH), 3.88 (s, 2H), 3.75 (s, 3H), 3.69 (s, 2H), 2.42 (s, 3H); ESI MS m/z 320 [M+ H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(3-Methoxyphenyl)-N-methylmethanamine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ALBANY MOLECULAR RESEARCH, INC.; WO2009/149258; (2009); A2;,
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Some common heterocyclic compound, 109-85-3, name is 2-Methoxyethylamine, molecular formula is C3H9NO, 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. Computed Properties of C3H9NO

To an ice-cooled solution of 2-methoxyethylamine (623 mg, 8.29 mmol) and triethylamine (1.50 mL, 10.8 mmol) in anhydrous DCM (50 mL) under argon was added dropwise chloroacetyl chloride (795 muL, 10.0 mmol). After 4 h the mixture was flushed through a Strata SI-1 silica cartridge (20 g Giga Tube), eluting with DCM. Fractions containing the target material (Rf 0.65, 100% EtOAc) were combined and evaporated to afford 2-chloro-N-(2-methoxyethyl)acetamide (1.14 g, 7.50 mmol; 90%) as a brown oil: deltaEta (300 MHz, CDCI3): 6.92 (1 H, br s), 4.02 (2 H, s), 3.44-3.49 (4 H, m), 3.34 (3 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 109-85-3, its application will become more common.

Reference:
Patent; UNIVERSITY COURT OF THE UNIVERSITY OF GLASGOW; HERIOT-WATT UNIVERSITY; MOUNTFORD, Joanne; MILLIGAN, Graeme; ADAMS, Dave; (95 pag.)WO2016/92327; (2016); 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. 1535-75-7, name is 2-(Trifluoromethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C7H6F3NO

. (2-Trifluoromethox -phenyl)-carbamic acid ethyl esterTo a solution of 2-(trifluoromethoxy)aniline (15.9 g, 0.09 mol) in DME (300 ml_) at -5 C (ice/salt bath) is added sodium hydride (3.6 g, 60% by weight, 0.09 mol) in portions. The suspension is warmed to r.t. and ethyl chloroformate (7.5 ml_, 0.08 mol) is added dropwise. The reaction mixture is stirred for 2 h at r.t. then heated to reflux for 1 .5 h. The mixture is then cooled to r.t. and water (150 ml_) is slowly added to quench the reaction. The phases are separated and the water layer is extracted with EtOAc (2×100 ml_). The combined organic layers are washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The crude material is purified on silica gel with EtOAc/heptanes (1 -5%) as eluent to afford the title product (1 1 .0 g, 49%) as an amber oil. 1 H NMR (300 MHz, CDCI3) delta 8.20 (d, J = 8.1 Hz, 1 H), 7.30-7.22 (m, 2H), 7.07 (app t, 1 H), 6.90 (br s, 1 H), 4.25 (q, J = 7.2 Hz, 2H), 1 .34 (t, J = 7.2 Hz, 3H);19F NMR (300 MHz, CDCI3) delta -57.32 (s, 3F);LC Rt: 2.96 min; MS 250 (M+1 , 94%).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1535-75-7.

Reference:
Patent; SANOFI; CHOI-SLEDESKI, Yong Mi; LIANG, Guyan; NIEDUZAK, Thaddeus R.; POLI, Gregory B.; SHUM, Patrick Wai-Kwok; STOKLOSA, Gregory T.; ZHAO, Zhicheng; WO2011/79102; (2011); A1;,
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Synthetic Route of 22236-10-8, 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. 22236-10-8, name is 4-(Difluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

The nitro ether (149 mmol) was dissolved in ethanol (37.5 mL), diluted with water (25 mL), and was treated with ammonium chloride (84.7 mmol) and iron powder EPO (105 mmol). The reaction mixture was heated at reflux for 30 minutes and the suspension was filtered through Celite. The filter cake was washed with ethanol three times and the combined filtrates were concentrated. The residue was dissolved in water and .the pH adjusted to 9-10 with 5 M sodium hydroxide. The aqueous layer was extracted with ethyl acetate (3xl00mL) and the combined organic layers were dried (magnesium sulfate) and concentrated to a yellow oil. The oil was dissolved in acetic anhydride (23.5 mmol) and the reaction mixture was maintained at rt for 16 h. The reaction mixture was diluted with water (50 mL) and was neutralized with solid sodium bicarbonate. The precipitated solids were isolated by filtration, washed with water, and dried to provide the acetamide in 62% yield as a light yellow solid.

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

Reference:
Patent; MEMORY PHARMACEUTICALS CORPORATION; WO2006/69097; (2006); A2;,
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