Tag: M.W=200-300

Synthetic Route of 99548-55-7, 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. 99548-55-7 name is Methyl 4-bromo-2-methylbenzoate, 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.

Preparation 35: 2-Methyl-4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)benzoic acid methyl ester 4-Bromo-2-methylbenzoic acid methyl ester (0.028 mmol), 4,4,5, 5,4′,4′,5′,5′- octamethyl-[2,2′]bi[[l,3,2]dioxaborolanyl] (0.028 mmol) and potassium acetate (0.064 mmol) were combined in dioxane (65 mL) and de-gassed with argon. [l,l’-bis(diphenylphosphino)- ferrocene]dichloropalladium (5.62xlO~4 mmol) and l,l’-bis(diphenylphosphino)ferrocene (5.62xlO~4 mmol) were added and the mixture stirred at 950C under argon for 16 h. The mixture was cooled then partitioned between water and ethyl acetate. The water was separated and washed with ethyl acetate. The organic extracts were combined, dried over MgSO4, concentrated and purified by dry-flash chromatography to afford the title compound: RT = 4.07 min; m/z (ES+)=277.24 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-bromo-2-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; PROSIDION LIMITED; WO2009/50522; (2009); A1;,
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Related Products of 87-13-8, 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. 87-13-8, name is Diethyl 2-(ethoxymethylene)malonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The quinolone derivatives 1 were prepared by treating the appropriate aniline (100 mmol) with diethyl ethoxymethylenemalonate (100 mmol) under reflux in ethanol (5 mL) for 2-10 h to obtain the enamine derivatives that were then cyclized in refluxing diphenyl ether for 30 min-6 h [29]. These quinolones (13 mmol) were refluxed in thionyl chloride (20 mL), for 17 h, affording the corresponding chloro-derivatives 2a-g [22]. Reaction of 2a-g (4 mmol) with 2-hydrazinobenzothiazole (8 mmol) in toluene (30 mL), for 3 h, followed by a 2 h reflux in acetic acid gave the corresponding 2-(benzo[d]thiazol-2-yl)-8-substituted-2H-pyrazolo[4,3-c]quinolin-3(5H)-ones 3a-g as solids which were collected by filtration under vacuum, washed with water and subsequent purified by washing with hot ethyl alcohol.

The synthetic route of Diethyl 2-(ethoxymethylene)malonate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Reis, Raisa Da R.; Azevedo, Elisa C.; De Souza, Maria Cecilia B.V.; Ferreira, Vitor Francisco; Montenegro, Raquel C.; Araujo, Ana Jersia; Pessoa, Claudia; Costa-Lotufo, Leticia V.; De Moraes, Manoel O.; Filho, Jose D.B.M.; De Souza, Alessandra M.T.; De Carvalho, Natasha C.; Castro, Helena C.; Rodrigues, Carlos R.; Vasconcelos, Thatyana R.A.; European Journal of Medicinal Chemistry; vol. 46; 4; (2011); p. 1448 – 1452;,
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Reference of 99548-55-7, These common heterocyclic compound, 99548-55-7, name is Methyl 4-bromo-2-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.

REFERENCE EXAMPLE 2; Methyl 4-bromo-2-(bromomethyl)benzoate; To a solution of methyl 4-bromo-2-methylbenzoate (9.60 g, 0.42 mol, obtained in reference example 1) in CCI4 (150 mL), Lambda/-bromosuccinimide (7.46g, 0.42mol) and benzoyl peroxide (0.19g, 0.79mmol) were added. The reaction mixture was stirred 4h at room temperature while irradiated with a 250 Watt lamp and it was then filtered to remove the precipitated solids. The filtrate was washed with 1 N NaOH and water and it was dried over Na2SO4. The solvent was evaporated to afford 11.87 g of the desired compound as an oil that solidified on standing (yield: 92%, uncorrected).1H NMR (300 MHz, CDCI3) delta (TMS): 3.94 (s, 3 H), 4.90 (s, 2 H), 7.51 (dd, J = 8.4 Hz, J’ = 2.1 Hz, 1 H), 7.63 (d, J = 1.8 Hz, 1 H), 7.84 (d, J = 8.4 Hz, 1 H).

The synthetic route of 99548-55-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; J. URIACH Y COMPANIA S.A.; WO2007/337; (2007); A1;,
Ester – Wikipedia,
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Related Products of 889858-12-2,Some common heterocyclic compound, 889858-12-2, name is tert-Butyl 4-bromo-2-fluorobenzoate, molecular formula is C11H12BrFO2, 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 250 mL round-bottom flask was added (1S,4S,5R)-5-[[4-cyclopropyl-l-(2,6- dichlorophenyl)-1H-l,2,3-triazol-5-yl]methoxy]-2-azabicyclo[2.2.1]heptane 52i (40 mg, 0.11 mmol, 1.00 equiv.), tert-butyl 4-bromobenzoate (40 mg, 0.16 mmol, 1.50 equiv.), Pd2(dba)3 (20 mg, 0.02 mmol, 0.20 equiv.), BINAP (26 mg, 0.04 mmol, 0.40 equiv.), Cs2CO3 (138 mg, 0.42 mmol, 4.00 equiv.), and toluene (5 mL). The resulting mixture was heated at 110°C overnight. After cooling to room temperature, the mixture was diluted with H2O (50 mL), and extracted with ethyl acetate (100 mL x 2). The combined organic extracts were washed with brine (100 mL x 2), dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography eluting with ethyl acetate/hexane (1 :2) to afford tert-butyl 4- [(1S,4S,5R)-5-[[4-cyclopropyl-l-(2,6-dichlorophenyl)-1H-l,2,3-triazol-5-yl]methoxy]-2- azabicyclo[2.2.1]heptan-2-yl]benzoate 52j (50 mg, 85percent) as a yellow oil.

The synthetic route of 889858-12-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; (231 pag.)WO2019/55808; (2019); A1;,
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Electric Literature of 10268-71-0,Some common heterocyclic compound, 10268-71-0, name is Phenyl 2-methoxybenzoate, molecular formula is C14H12O3, 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.

5,6-Dihydro-cyclopenta[b]thiophen-4-one (2.1 g, 15.0 mmol) in 15 mL of THF was treated with NaH (60 percent, 1.5 g, 36 mmol). After the addition of 2-Methoxy-benzoic acid phenyl ester, the reaction mixture was heated at 100 C. for 8 hr. The solution was cooled to room temperature and poured into water. The resulting mixture was acidified with concentrated HCl and was added with ethyl acetate (70 mL). The organic layer was collected, brined, dried over MgSO4(s), and concentrated under reduced pressure. The resultant precipitate was collected and recrystallized from ethanol to provide the corresponding 5-(2-Methoxy-benzoyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one (2.53 g, 8.3 mmol) as yellow solid in 59% yield.

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

Reference:
Patent; DEVELOPMENT CENTER FOR BIOTECHNOLOGY; LIAO, Chu-Bin; CHIANG, Chao-Cheng; YANG, Huei-Ru; LIAO, Yuan-Chun; CHEN, Paonien; US2013/274255; (2013); A1;,
Ester – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 618-89-3, name is Methyl 3-bromobenzoate, 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 618-89-3, SDS of cas: 618-89-3

3-(3-bromophenyl)-3-oxopropanenitrile: Acetonitrile (21.86 mL, 419 mmol) was added to a stirred suspension of 60% NaH (7.25 g, 181 mmol) in THF (150 mL). Then, methyl 3-bromobenzoate (30 g, 140 mmol) was added and the mixture was heated at 75C for 4 h. After cooling to room temperature, water followed by iN HC1 (200 mL) was added and the mixture was extracted with ethyl acetate (500 mL), washed with sat .NaHCO3 solution (200 mL), dried (Na2SO4), filtered andconcentrated to afford 3-(3-bromophenyl)-3-oxopropanenitrile (29 g, 129 mmol, 93% yield) as light yellow solid. ?H NMR (500 MHz, CDC13) oe 8.09 (t, J1 .7 Hz, 1H),7.90 – 7.86 (m, 1H), 7.83 (ddd, J8.0, 2.0, 1.1 Hz, 1H), 7.45 (t, J7.9 Hz, 1H), 4.08(s, 2H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NAIDU, B. Narasimhulu; PATEL, Manoj; D’ANDREA, Stanley; ZHENG, Zhizhen Barbara; CONNOLLY, Timothy P.; LANGLEY, David R.; PEESE, Kevin; WANG, Zhongyu; WALKER, Michael A.; KADOW, John F.; WO2015/126376; (2015); A1;,
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Electric Literature of 55666-43-8,Some common heterocyclic compound, 55666-43-8, name is tert-Butyl 3-bromopropanoate, molecular formula is C7H13BrO2, 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 5-bromo-2-(phenylcarbonyl)-1 ,2-dihydro-1 -isoquinolinecarbonitrile (D10; 70 g, 206 mmol) and 1 , 1 -dimethylethyl 3-bromopropanoate (Aldrich; 37.9 ml, 227 mmol) in dry, degassed DMF (250ml) was added dropwise over 40 mins to a suspension of sodium hydride (60%; 24.76 g, 619 mmol) in dry, degassed DMF (750ml) at -10 0C under nitrogen. The mixture was stirred at -10 0C for 10 mins, then allowed to warm to room temp over 3h. Water (1500ml) was cautiously added and the mixture extracted with ethyl acetate (3x500ml). The combined organic extracts were washed with brine (5x500ml) and dried (MgSO4). The solvent was evaporated to give a brown oil. The crude intermediate was dissolved in THF (700ml) and lithium hydroxide (24.71 g, 1032 mmol) in water (100 ml) (note: not all soluble) was added. The mixture was vigorously stirred for 3Oh, then stored in the fridge over the weekend. The mixture was partitioned between water (700ml) and ethyl acetate (3x500ml) and the combined organic extracts washed with brine (2x500ml) and dried (MgSO4). The solvent was evaporated and the residue was purified by chromatography on silica eluting with 5-15% ethyl acetate in isohexane gave the title compound (48.2g) MS (ES) Ci6H18BrNO2 requires 336; found 336/338 [M+H]+.

The synthetic route of 55666-43-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/133136; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 26759-46-6, 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. 26759-46-6, name is Methyl 2-amino-4,5-dimethoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 1.5 equiv of PMBONH3+Cl- plus 4.5 equiv of LiHMDS (at 0 °C for 2 h) or 4.1 equiv of LDA (from -78 °C to -10 °C, 0.5 h); yields were similar.

The synthetic route of Methyl 2-amino-4,5-dimethoxybenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bosch, Llui?s; Mouscadet, Jean-Franois; Ni, Xio-Ju; Vilarrasa, Jaume; Tetrahedron Letters; vol. 52; 7; (2011); p. 753 – 756;,
Ester – Wikipedia,
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Some common heterocyclic compound, 40546-94-9, name is 6-Methyl-4-phenylchroman-2-one, molecular formula is C16H14O2, 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. Application In Synthesis of 6-Methyl-4-phenylchroman-2-one

Sodium borohydride (0.76 g, 20 mmol) is added in small portions to the cooled solution of 7-methyl-4-phenyl-3,4-dihydrocoumarin (compound of formula I) (0.48 g, 2 mmol) in 20 ml of methanol. The reaction mixture is stirred for 1 h at 0 C and 4 h at room temperature. The reaction mixture is poured into 1 mol/l solution of hydrochloric acid (120 ml) and extracted with ethyl acetate (3 x 70 ml). The combined organic fractions are dried over anhydrous magnesium sulphate and the solvent evaporated to give the product in 70 % yield (0.49 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 40546-94-9, its application will become more common.

Reference:
Patent; LEK PHARMACEUTICALS D.D.; WO2006/66931; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 6232-12-8, 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. 6232-12-8, name is Ethyl 4-(aminomethyl)benzoate hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of compound 33c (600 mg, 2.24 mmol) in THF(6.0 mL) were added oxalyl chloride (0.590 mL, 6.72 mmol) andN,N-dimethylformamide (1 drop). After being stirred for 1 h atroom temperature, the mixture was concentrated in vacuo. Theresidue was resuspended in THF (6.0 mL), and to the mixture wereadded ethyl 4-(aminomethyl)benzoate hydrochloride (965 mg,4.48 mmol) and triethylamine (1.20 mL, 8.96 mmol). After beingstirred for 12 h at room temperature, the mixture was concentratedin vacuo. The residue was taken up in ethyl acetate, washedwith 1 M hydrochloric acid (2), saturated sodium hydrogen carbonatesolution, 1 M hydrochloric acid, brine, dried over Na2SO4and concentrated in vacuo. The residue was crystallized from ethylacetate to give 34b (771 mg, 80%) as a white powder. mp 227-228 C. 1H NMR (300 MHz, DMSO-d6) d 1.31 (3H, t, J = 6.2 Hz),1.36 (3H, t, J = 6.2 Hz), 4.31 (2H, q, J = 7.1 Hz), 4.40 (2H, q,J = 7.1 Hz), 4.65 (2H, d, J = 5.5 Hz), 7.50 (2H, d, J = 8.5 Hz), 7.93(2H, d, J = 8.5 Hz), 8.57 (1H, s), 11.3 (1H, s), 13.5 (1H, s). Anal. Calcdfor C20H19N3O6S0.20H2O: C, 55.47; H, 4.52; N, 9.70. Found: C,55.50; H, 4.39; N, 9.73.

The chemical industry reduces the impact on the environment during synthesis Ethyl 4-(aminomethyl)benzoate hydrochloride. I believe this compound will play a more active role in future production and life.

Reference:
Article; Nara, Hiroshi; Sato, Kenjiro; Naito, Takako; Mototani, Hideyuki; Oki, Hideyuki; Yamamoto, Yoshio; Kuno, Haruhiko; Santou, Takashi; Kanzaki, Naoyuki; Terauchi, Jun; Uchikawa, Osamu; Kori, Masakuni; Bioorganic and Medicinal Chemistry; vol. 22; 19; (2014); p. 5487 – 5505;,
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