Tag: M.W=200-300

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. 939-18-4, name is 3-Bromo-2H-chromen-2-one belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 939-18-4

General procedure: Typically, (hetero)aryl bromide (1.0 mmol), thiazole derivatives(2.0 mmol), Pd-PEPPSI complexes (0.01e0.5 mol%), base (2 mmol),acid additive (0.3 mmol), and 3mL of DMAc solvent were addedinto a parallel reactor. After heating at 130 C for 4 h, the resultingmixture was cooled to room temperature. Subsequently, 25mL ofwater and 20 mL of dichloromethane were added into the reactor,and the mixture was stirred for another several minutes, followedby extraction three times with dichloromethane (3 x 5 mL). Theorganic layer was then combined, dried over anhydrous sodiumsulfate, filtered, and evaporated under reduced pressure to give thecrude products. The crude products were then purified by silica-gelcolumn chromatography using petroleum etheredichloromethane(15/1) as the eluent. The obtained pure products were characterizedby 1H NMR and 13C NMR spectroscopy, and the spectra can be foundin the Supporting Information. And the isolated yields of productswere obtained based on the amounts of (hetero)aryl bromides.

The synthetic route of 939-18-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ma, Bei-Bei; Lan, Xiao-Bing; Shen, Dong-Sheng; Liu, Feng-Shou; Xu, Chang; Journal of Organometallic Chemistry; vol. 897; (2019); p. 13 – 22;,
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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. 1186-73-8, name is Trimethyl methanetricarboxylate, A new synthetic method of this compound is introduced below., Safety of Trimethyl methanetricarboxylate

Step 3; methyl 9-chloro-l-(2,4-dimethoxybenzyl)-4-hydroxy-7-methyl-2-oxo-2,5,6,7- tetrahydro-lH-benzo [b] pyrido [2,3-d] azepine-3-carboxylate Crude N-(8-chloro-l-methyl-3,4-dihydro-lH-benzo[b]azepin-5(2H)-ylidene)-l-(2,4- dimethoxyphenyl)methanamine (690 mg, 1.95 mmol) and trimethyl methanetricarboxylate (631 mg, 3.32 mmol) were mixed together in Pl^O (4.0 mL). With stirring, the mixture was placed into a pre-heated heat block at 210 C and heated for 10 minutes under a blanket of Argon. The reaction mixture was cooled to room temperature and was filtered directly on a silica cartridge. The product was purified by column chromatography (100% hexanes followed by EtOAc in hexanes 0 to 85% gradient) to provide the desired product (289 mg, 31%, two steps) as an off-white foam which was used directly in the next step. LC-MS 483.9 [M-H]”, 485.8 [M+H]+, RT 1.53 min.

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; PTC THERAPEUTICS, INC.; BRANSTROM, Arthur; JOSYULA, Vara Prasad, Venkata Nagendra; ARNOLD, Michael, Andrew; GERASYUTO, Aleksey, I.; KARP, Gary; WANG, Jiashi; WO2013/33228; (2013); 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. 34529-06-1, name is Dimethyl 3-aminophthalate, A new synthetic method of this compound is introduced below., Formula: C10H11NO4

Example 7 3-(3-Ethoxy-4-methoxy-phenyl)-3-(4-isobutylamino-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionitrile To a mixture of dimethyl-3-aminophthalic ester (0.75 g, 3.6 mmol), 3-methyl-butyraldehyde (0.36 mL, 4.0 mmol), acetic acid (1.3 mL, 23 mmol) in 1,2-dichloroethane (30 mL), was added sodium triacetoxyborohydride (1.5 g, 7.2 mmol) at room temperature. After 30 minutes, the mixture was extracted with methylene chloride (30 mL) and water (30 mL). The organic layer was washed with sodium hydrogen carbonate (sat. 30 mL). The solvent was removed in vacuo to give a yellow oil. To the oil in methanol (5 mL), was added sodium hydroxide (10 N, 1.5 mL), and kept at room temperature overnight. To the mixture, was added HCl (12 N, 1.3 mL). The solvent was removed in vacuo to give a solid. The solid was dissolved in pyridine (10 mL), and 3-amino-3-(3-ethoxy-4-methoxy-phenyl)-propionitrile (1.0 g, 3.6 mmol) was added to the solution. The solution was heated to reflux for 2 days. The solvent was removed in vacuo to give an oil. The oil was extracted with ethyl acetate (100 mL) and water (100 mL). The organic layer was washed with water (50 mL), HCl (1N, 2*50 muL), water (50 mL), sodium hydrogen carbonate (sat, 2*50 mL), and brine (50 mL), and dried over MgSO4. Filtration and removal of solvent in vacuo gave an oil. The oil was purified by column chromatography (Silca Gel, 1:3 EtOAc:hexanes) to give 3-(3-ethoxy-4-methoxy-phenyl)-3-(4-isobutylamino-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionitrile as a yellow solid (700 mg, 46% yield): mp, 12-123 C.; 1H NMR (CDCl3) delta 1.01 (d, J=7 Hz, 6H, 2CH3), 1.45 (t, J=7 Hz, 3H, CH3), 1.88-1.99 (m, 1H, CH), 3.07 (t, J=6 Hz, 2H, CH2), 3.27 (dd, J=7, 17 Hz, 1H, CHH), 3.76 (dd, J=10, 17 Hz, 1H, CHH), 3.84 (s, 3H, CH3), 4.09 (q, J=7 Hz, 2H, CH2), 5.55 (dd, J=7, 10 Hz, 1H, NCH), 6.37 (t, J=6 Hz, 1H, Ar), 6.81-6.86 (m, 2H, Ar), 7.01-7.06 (m, 3H, Ar), 7.44 (t, J=8 Hz, 1H, Ar); 13C NMR (CDCl3) delta 14.69, 20.26, 21.29, 28.27, 50.31, 50.63, 55.95, 64.49, 109.63, 111.10, 111.42, 112.22, 116.58, 117.09, 119.96, 129.55, 132.33, 135.93, 147.14, 148.53, 149.66, 168.18. Analy. Calculated for C24H27N3O4: C, 68.39; H, 6.46; N, 9.97. Found: C, 68.32; H, 6.39; N, 9.95.

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; Muller, George W.; Man, Hon-Wah; US2006/84815; (2006); A1;,
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Electric Literature of 40876-98-0, These common heterocyclic compound, 40876-98-0, name is Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate, 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.

ethyl-2-(4-((1R,3R)-8-(bicyclo[4.3.1]decan-8-yl)-8-azabicyclo[3.2.1]octan-3-yl)-3-oxo-3,4-dihydroquinoxalin-2-yl)acetate (d15) To a solution of c6 (700 mg, 1.980 mmol) in toluene (14 mL) was added AcOH (0.249 mL, 4.36 mmol) and diethyl oxalacetate sodium salt (499 mg, 2.376 mmol) at a temperature of about 25 C. under a nitrogen atmosphere. The mixture was stirred at 100 C. for 2.5 hr. After cooling to a temperature of about 25 C. and concentration, the resulting oil was chromatographed (ISCO, 80 g, CHCl3/10% NH3 in MeOH=99/1?95/5) to provide 806 mg of d15 as a brown amorphous solid. (Yield 85.2%) d15: 1H-NMR (300 MHz, CDCl3) delta: 1.24-1.46 (m, 6H), 1.59-1.77 (m, 10H), 2.06 (s, 3H), 2.07-2.31 (m, 8H), 2.60 (s, 2H), 3.93 (s, 2H), 4.21 (q, J=7.1 Hz, 4H), 5.74 (s, 1H), 7.04 (s, 1H), 7.33 (d, J=11.6 Hz, 2H), 7.60 (s, 1H); LC/MS: m/z=493.3 [M+H]+ (Calc: 492.61).

Statistics shows that Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate is playing an increasingly important role. we look forward to future research findings about 40876-98-0.

Reference:
Patent; Shionogi & Co., Ltd.; Purdue Pharma L.P.; MARRA, Jeffrey Michael; Tsuno, Naoki; Ueno, Tatsuhiko; Zhou, Xiaoming; US2014/187544; (2014); A1;,
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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. 32454-33-4, name is Methyl 2-(3-methoxyphenyl)-2-methylpropanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: esters-buliding-blocks

Step B; 2-(3-Methoxy-phenyl)-2-methyl-propionic acid methyl ester 78 (2.77 g, 13.3 mmol) is dissolved in dry DCM (17 mL). The solution is cooled to -65C. boron tribromide (4.33 g, 17.3 mmol) dissolved in DCM (17 mL) is added. The reaction mixture is stirred at -650C for 90 min. Then the mixture is quenched with MeOH. Solvents are removed in vacuo, the remainder is diluted with ethyl acetate and washed with 0.2 N HCl. The aqueous phase is exrtacted with ethyl acetate. The organic layers are combined, washed with water and brine, dried over MgSO4, filtered and concentrated. Silica gel chromatography (0-25% ethyl acetate in hexanes) yielded 79 as a light yellow oil. 1H-NMR (400 MHz, CDCl3) delta = 7.25 (t, J= 8.0 Hz, IH)5 6.97-6.94 (m, IH), 6.88 (s, IH), 6.79-6.76 (m, IH), 3.72 (s, 3H), 1.62 (s, 6H); MS calcd. for CnHi4NaO3 (M+Na4) 217.1, found 217.1.

The synthetic route of 32454-33-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; WO2007/56497; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 35450-36-3, 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 35450-36-3 as follows.

To a cold solution (ice water bath) of the methyl-2-bromo-5-methoxybenzoate (2.00 g, 8.16 MMOL) in DICHLOROMETHANE (15 mL) was added AIC13 (5.44 g, 40.8 MMOL) under argon, and the reaction temperature was maintained BELOW 10C using an ice-water bath. The light brown suspension was stirred for 10 min, then EtSH (3.02 mL, 40.8 MMOL) was added dropwise at such a rate that the reaction temperature was maintained BELOW 5C. After 2.5 h of stirring below 10C, the reaction mixture was slowly poured into ice water with agitation. The organic layer was separated, and the aqueous layer was extracted with DCM. The combined organic layers were washed with water, dried over MGS04, filtered and concentrated under reduced pressure to afford a light yellow oil which was used in the next step without further purification.

According to the analysis of related databases, 35450-36-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2004/50650; (2004); 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. 41841-16-1, name is Methyl 2-(4-bromophenyl)acetate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

Methyl 2-(4-bromophenyl)propanoate. To a solution of lithium diisopropylamide (2 mol/L, 22 mL, 44 mmol) in tetrahydrofuran (80 mL) was dropwise a solution of methyl 2-(4- bromophenyl)acetate (10 g, 44 mmol) in tetrahydrofuran (20 mL) at -78 C. The mixture solution was stirred for 0.5 hour at that temperature, then iodomethane (8 g, 56 mmol) was added. The mixture was stirred for 10 minutes at – 78 C, then was removed from the cooling bath and stirred for 0.5 hour. The reaction was quenched with sat. ammonium chloride, then diluted with ethyl acetate, washed with water, The organic layer concentrated to dry, purified by column chromatography (silica-gel, petroleum : ethyl acetate= 20 : 1) to give methyl 2-(4- bromophenyl)propanoate as a colorless oil (10 g, 91 %). 1H NMR (300 MHz, CDC13): delta 7.44 (d, J = 9 Hz, 2H), 7.17 (d, J = 9 Hz, 2H), 3.65-3.70 (m, 4H), 1.48 (d, J = 6 Hz, 3H).

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; CONSTELLATION PHARMACEUTICALS; ALBRECHT, Brian, K.; AUDIA, James, Edmund; COOK, Andrew; GAGNON, Alexandre; HARMANGE, Jean-christophe; NAVESCHUK, Christopher, G.; WO2013/75083; (2013); A1;,
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Related Products of 51760-21-5, 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. 51760-21-5, name is Dimethyl 5-bromoisophthalate, This compound has unique chemical properties. The synthetic route is as follows.

A (2 g, 11 mmol), B (2 g, 7.4 mmol), CsF (3 g, 15 mmol) and Pd(PPh3)4 (0.2 g, 0.17 mmol) was added to a 250 mE flask. The flask was connected to Schlenk line. 200 mE 1 ,2-Dimethoxyethane was degassed and added through a canula. The flask was equipped with a water condenser and refluxed under the nitrogen for 48 hours. The solution was dried on rotary evaporator. 100 mE H20 was added and then extract with CHC13. The organic phase was evaporated to dryness and purified with chloroform through a short silica gel colunm to yield a light yellow powder 1.56 g. (Yield:62%). ?H NMR (CDC13): oe=3.97 (s, 9H), 7.90 (d, 2H), 8.06 (d, 2H), 8.44 (d, 2H) 8.49 (t, 1H).

The chemical industry reduces the impact on the environment during synthesis Dimethyl 5-bromoisophthalate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Zhou, Hong-Cai; Feng, Dawei; Wang, Kecheng; US2015/152123; (2015); A1;,
Ester – Wikipedia,
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Synthetic Route of 148547-19-7, 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 148547-19-7 as follows.

BINAP (0.67 g; 1.1 mmol; 0.05 eq.) and palladium acetate (0.24 g; 1.1 mmol; 0.05 eq.) were added to a suspension methyl 4-bromo-3-methylbenzoate (5 g; 21.8 mmol; 1 eq.), CS2CO3 (10.65 g; 32.7 mmol; 1 .5 eq.) and piperidine (2.2 g; 26 mmol; 1.2 eq.) in dioxane (100 mL) and the reaction mixture was refluxed for 15 hours. After filtration through a pad of Celite, the solution was concentrated in vacuo and the residue purified by column chromatography (petroleum ether/ethyl acetate, 80/20) to afford the title compound (4.9 g, 96%) as a brown solid.LC/MS : 233.9 (M+H)+. 1H NMR (CDCI3, 400 MHz) delta 7.84-7.82 (m, 2H), 6.99-6.97 (m, 1 H), 3.92 (s, 3H), 2.93-2.90 (m, 4H),1.76-1.67 (m, 4H, m), 1.63-1.62 (m, 2H).

According to the analysis of related databases, 148547-19-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SERONO S.A.; WO2009/43890; (2009); A1;,
Ester – Wikipedia,
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Application of 721-63-1, 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 721-63-1 as follows.

Step B: Ethyl 2-bromo-2-(4-(trifluoromethyl)phenyl)acetate To a solution of ethyl 2-(4-(trifluoromethyl)phenyl)acetate (5 g, 21.5 mmol) in CC14 (100 mL) was added NBS (11.5 g, 64.6 mmol). The resulting mixture was heated to reflux and stirred for 16 hr. The reaction mixture was then filtered and the filtrate was evaporated to dryness. The residue was purified via CombiFlash (80 g column, DCM in Petroleum ether from 0% to 30%) to give ethyl 2-bromo-2-(4-(trifluoromethyl)phenyl)acetate as an oil. NMR (CDC13, 400 MHz): 5 7.68 (d, J= 8.0 Hz, 2H), 7.63 (d, J= 8.0 Hz, 2H), 5.35 (s, 1H), 4.33-4.18 (m, 2H), 1.30 (t, J = 7.0 Hz, 3H).

According to the analysis of related databases, 721-63-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; CAI, Jiaqiang; CRESPO, Alejandro; DU, Xiaoxing; DUBOIS, Byron Gabriel; GUIADEEN, Deodialsingh; KOTHANDARAMAN, Shankaran; LIU, Ping; LIU, Rongqiang; QUAN, Weiguo; SINZ, Christopher; WANG, Liping; (285 pag.)WO2016/49099; (2016); A1;,
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