Category: esters-buliding-blocks

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. 37746-78-4, name is (E)-Ethyl 4-bromobut-2-enoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: (E)-Ethyl 4-bromobut-2-enoate

General procedure: To a vigorously stirring solution of alpha-imino ester 1 (0.5 mmol,1 equiv) and E-ethyl-4-bromocrotonate or methyl-4-bromocrotonate (2, 1.5 mmol, 3 equiv) in EtOH (2 mL) was added indium powder (1 mmol, 2 equiv). The mixture was allowed to stir vigorously for 6 h at 30 C. After this period, the reaction mixturewas quenched with 2 mL of water and transferred to a separating funnel and extracted using ethyl acetate (315 mL). The combined organic layers were dried over anhydrous Na2SO4. Then the solvent was evaporated under vacuum. Purification of the resulting crude reaction mixture by column chromatography on silica gel (EtOAc/Hexane as eluent) gave the product 3 (see Tables 1 and 2 and Scheme 2 for individual entries).

The synthetic route of 37746-78-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Aslam, Nayyar Ahmad; Babu, Srinivasarao Arulananda; Sudha, Arya Jayadev; Yasuda, Makoto; Baba, Akio; Tetrahedron; vol. 69; 32; (2013); p. 6598 – 6611;,
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Synthetic Route of 99548-55-7, 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. 99548-55-7, name is Methyl 4-bromo-2-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows.

Example 33B Methyl 4-bromo-2-(bromomethyl)benzoate A solution of Example 33A (1.02 g, 4.47 mmol) in CCl4 (22 mL) was treated with AIBN (0.065 g, 0.4 mmol) and NBS (0.955 g, 5.4 mmol), heated to reflux for 4 hours, washed with water, dried (Na2SO4), filtered, and concentrated to provide the desired product (1.1 g, 79%).

The chemical industry reduces the impact on the environment during synthesis Methyl 4-bromo-2-methylbenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Li, Qun; Woods, Keith W.; Zhu, Gui-Dong; Fischer, John P.; Gong, Jianchun; Li, Tongmei; Gandhi, Virajkumar; Thomas, Sheela A.; Packard, Garrick K.; Song, Xiaohong; Abrams, Jason N.; Diebold, Robert; Dinges, Jurgen; Hutchins, Charles; Stoll, Vincent S.; Rosenberg, Saul H.; Giranda, Vincent L.; US2003/187026; (2003); A1;,
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Adding a certain compound to certain chemical reactions, such as: 5335-05-7, name is Chloromethyl benzoate, belongs to esters-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 5335-05-7, Safety of Chloromethyl benzoate

To a stirred mixture of with NaH (60%, 50 mg, 1.3 mmole) in anhydrous DMF (6 mL) at room temperature under nitrogen was added 2-(6-(4-(2-(tert-butyl-dimethylsilyloxy)ethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide, 10 (0.20 g, 0.34 mmole). The resultant mixture was stirred at room temperature for 8 min., then treated with chloromethyl benzoate (0.2 g, 1.2 mmole), the reaction mixture was stirred at room temperature overnight. The reaction mixture was added with aqueous NH4Cl solution and extracted with EtOAc (3×45 mL). The EtOAc solution was washed with 10% LiCl solution and concentrated to an oily residue. The residue was purified by prep. HPLC to give a white solid as impure product and used directly in next step. MS (ESI, M+H+) 736, 738.

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Reference:
Patent; Kim, Kyoung S.; Lee, Francis Y.; Lombardo, Louis J.; Luo, Feng Roger; Wityak, John; US2006/69101; (2006); A1;,
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Some common heterocyclic compound, 27798-60-3, name is Methyl 2-Methoxyphenylacetate, molecular formula is C10H12O3, 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. name: Methyl 2-Methoxyphenylacetate

Triflic acid (7.3 mL, 43.4 mmol) was added dropwise to a solution of thioxanthone oxide (5.00 g, 21.7 mmol) and methyl 2-(2-methoxyphenyl)acetate (4.31 g, 23.9 mmol) in DCM (60 mL) at -78 C. and slowly warmed to 25 C. overnight. The reaction mixture was quenched with water (100 mL), the layers separated, and the aqueous phase washed with water (4×100 mL) and concentrated to a crude solid. The crude solid was dissolved in minimal acetone, precipitated into MTBE (1 L), and filtered to afford the title compound (10.0 g, 85%) as a white solid. 1H NMR (500 MHz, (CD3)2CO) delta: 8.66-8.69 (m, 2H), 8.19-8.22 (m, 3H), 8.10-8.13 (m, 4H), 7.91 (d, J=2.5 Hz, 1H), 7.37 (d, J=9 Hz, 1H), 3.96 (s, 3H), 3.61 (s, 2H), 3.57 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 27798-60-3, its application will become more common.

Reference:
Patent; Rohm and Haas Electronic Materials, LLC; LaBeaume, Paul J.; (24 pag.)US9304394; (2016); B2;,
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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. 41841-16-1, name is Methyl 2-(4-bromophenyl)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C9H9BrO2

To a stirred solution of 100 g methyl-(4-bromophenyl)acetate(9, 0.436 mol) in 300 cm3 tetrahydrofuran, 95 g sodium methoxide (1.75 mol) was added at 0-5 C and maintained for 1 h. 80 g dimethyl carbonate (0.88 mol)was added at 0-5 C over a period of 2 h. The reaction mass was maintained at 25-30 C until the completion ofthe reaction (monitored by HPLC). After completion of the reaction, tetrahydrofuran was concentrated under reduced pressure at 45 C to obtain the syrup. The syrup was diluted in 500 cm3 water and the product was extracted in250 cm3 dichloromethane. The organic layer was concentrated under reduced pressure at 45 C to obtain the thick solution which was dissolved in 200 cm3 isopropyl alcoholat 70 C and maintained for 1 h. The solution was cooled to 0 C and maintained for 60 min. The obtained solid was filtered, washed with isopropyl alcohol, and dried at 50-55 C for 4-6 h to provide 10. Yield: 80 g; purity by HPLC: 99%; m.p.: 72-76 C. The spectral data of compound 10 were found to agree with the reported data [8].

The synthetic route of 41841-16-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jagtap, Kunal M.; Niphade, Navnath C.; Gaikwad, Chandrashekhar T.; Shinde, Gorakshanath B.; Toche, Raghunath B.; Joshi, Divyesh R.; Mathad, Vijayavitthal T.; Monatshefte fur Chemie; vol. 149; 3; (2018); p. 653 – 661;,
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Related Products of 18595-14-7, These common heterocyclic compound, 18595-14-7, name is Methyl 4-amino-3-methylbenzoate, 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 mixture of compound 1 (429 mg, 0.0026 mol) and NBS (0.7 g, 0.0039 mol) in DCM was stirred at r.t. for 3 h. The mixture was concentrated to a residue, which was purified by Prep-TLC to obtain compound 2 (522 mg, 83%) as a light yellow solid

The synthetic route of 18595-14-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; van Duzer, John H.; Mazitschek, Ralph; US2014/128391; (2014); A1;,
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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 40872-87-5 as follows. Product Details of 40872-87-5

Triethylamine (1.16 g, 11.5 mmol) was added to a mixture of 7-methoxy-2-oxo-1,2-dihydro-[1,6]naphthyridine-3-carboxylic acid (from Example 15 supra) (2.3 g, 10.45 mmol) and HATU (4.37 g, 11.5 mmol) in dry DMF (30 mL). The resulting mixture was stirred at room temperature until clear solution was obtained. 3-Amino-4-chloro-benzoic acid methyl ester (2.32 g, 12.55 mmol) was added and the resulting mixture was stirred for another 20 hours. The reaction mixture was diluted with water (300 mL), aqueous saturated NaHCO3 (60 mL) and ethyl acetate (150 mL). After thorough mixing, off white precipitate was collected by filtration, washed water, ethyl acetate and MeOH, and dried under reduced pressure to give 4-chloro-3-[(7-methoxy-2-oxo-1,2-dihydro-[1,6]naphthyridine-3-carbonyl)-amino]-benzoic acid methyl ester as an off-white solid. (Yield 2.9 g, 71.8%). 1H NMR (300 MHz, d6-DMSO) delta 12.42 (s, 1H), 9.18 (s, 1H), 9.01 (s, 1H), 8.91 (s, 1H), 7.70 (d, 2H, J=1.1 Hz), 6.61 (s, 1H), 3.95 (s, 3H), 3.89 (s, 3H). LC-MS: [M+H]+ 388.

According to the analysis of related databases, 40872-87-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Luk, Kin-Chun; US2012/184562; (2012); A1;,
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Reference of 54535-22-7, A common heterocyclic compound, 54535-22-7, name is Diethyl 2-((phenylamino)methylene)malonate, molecular formula is C14H17NO4, 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.

j00330J A 1 L three-necked flask fitted with a mechanical stirrer was charged with 2- phenylaminomethylene-malonic acid diethyl ester (26.3 g, 0.100 mol), polyphosphoric acid (270 g) and phosphoryl chloride (750 g). The mixture was heated to 70 C and stirred for 4 h. The mixture was cooled to room temperature and filtered. The residue was treated with aqueous Na2CO3 solution, filtered, washed with water and dried. 4- Hydroxyquinoline-3-carboxylic acid ethyl ester was obtained as a pale brown solid (15.2 g, 70%). The crude product was used in next step without further purification.

The synthetic route of 54535-22-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHU, Cathy; DOKOU, Eleni; HASELTINE, Eric L.; MOSKOWITZ, Samuel; OVERHOFF, Kirk A.; ROBERTSON, Sarah; WALTZ, David; (204 pag.)WO2019/10092; (2019); A1;,
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Application of 924-99-2,Some common heterocyclic compound, 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, molecular formula is C7H13NO2, 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 solution of MeCN (1 mmol) containing chromene diene 13 (0.5 mmol) and the corresponding enamino ester 9 or? -enaminokone 11 (0.6 mmol) shown in Table 1 3.0 mL) was stirred at room temperature while adding indium (III) trifluoromethanesulfonate [Indium (III) trifluoromethanesulfonate].The reaction mixture was stirred for 2-8 hours, and after completion of the reaction was confirmed by TLC (hexane-EtOAc, 4: 1, v / v), 10 mL of water was added and the solution was extracted with ethyl acetate (10 mL x 3) .The solvent was evaporated and the residue was subjected to silica gel column chromatography using hexane-ethyl acetate (4: 1, v / v) to obtain the following compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 3-(dimethylamino)acrylate, its application will become more common.

Reference:
Patent; Yeungnam University Industry-Academic Cooperation Foundation; Lee Yong-rok; (31 pag.)KR2018/3669; (2018); 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. 18595-14-7, name is Methyl 4-amino-3-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 18595-14-7

Into a 500-mL round-bottom flask was placed a solution of methyl 4-amino-3-methylbenzoate (4.00 g, 24.2 mmol, 1.00 equiv) and NaSCN (7.00 g, 86.4 mol, 3.57 equiv) in AcOH (90 mL) that was cooled to 0 C. This was followed by the addition of a solution of Br2 (3.9 g, 25 mmol, 1.0 equiv) in AcOH (25 mL) dropwise, maintaining at 0 C over 20 min. The resulting solution was allowed to warm to RT on its own accord (over approximately 10 min.) and stirred for 48 hrs at RT. At this time, the solids of the reaction were filtered out. The resulting solution was diluted with 100 mL H20. The pH value of the solution was adjusted to 8-9 with ammonia (using Whatman PH strip paper to monitor PH adjustment) which furnished an immediate precipitation. The solids were collected by filtration and washed once with ice cold MeOH (50 mL) to afford as a yellow solid. MS m/z 223.0 (M+l). 1H NMR (400 MHz, MeOH- 4) delta 8.17 (app d, J = 1.0 Hz, 1H), 8.03 (br s, 2H, NH2), 7.68 (s, 1H), 3.82 (s, 3H), 2.42 (s, 3H).

According to the analysis of related databases, 18595-14-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IRM LLC; TULLY, David C.; RUCKER, Paul Vincent; ALPER, Phillip B.; MUTNICK, Daniel; CHIANELLI, Donatella; WO2012/87519; (2012); A1;,
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