Month: March 2021

106614-28-2, name is Methyl 2,4-difluorobenzoate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Computed Properties of C8H6F2O2

0.80mL fuming nitric acid was added dropwise 5mL concentrated sulfuric acid, stirred for 5min,Methyl 2,4-difluorobenzoate was added dropwise(1.50g, 8.71mmol, 1.0eq), and then reacted at room temperature for 30min, poured into ice water to precipitate a white solid, which was suction filtered to give a white solidProducts, dry, white solid product 1.8g.

The synthetic route of 106614-28-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sun Yat-sen University; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Kou Yuhui; Hu Bolin; Jiang Haigang; Ye Jiuyong; Liu Zhiqiang; Xie Hongming; Zhang Yingjun; Yan Ming; (39 pag.)CN106749233; (2017); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 10203-58-4, The chemical industry reduces the impact on the environment during synthesis 10203-58-4, name is Diethyl isobutylmalonate, I believe this compound will play a more active role in future production and life.

To a solution of 8.34 g (38.6 mmol) of diethyl isobutylmalonate in 35 mL of 95% EtOH was added a solution of 9.0 g (161 mmol) of KOH in 110 mL of 95% EtOH. The mixture was stirred at 25 C. for 16 hours and then at reflux for 1 hour. The mixture was cooled, diluted with water and extracted with CH3 Cl. The aqueous layer was cooled to 0 C. and acidified to pH<1 with 30 mL of concentrated HCl, then it was extracted with CHCl3. The aqueous layer was further continuously extracted with CHCl3 overnight. The combined organic extracts were dried over anhydrous Na2 SO4 and evaporated to afford 5.44 g (33.9 mmol, 88%) of isobutylmalonic acid as a solid which was essentially pure according to 1 H NMR and which was used without further purification. Characteristic analytical data are as follows: mp 108-110 C.; 1 H NMR (300 MHz, CDCl3) delta3.52 (t, J=8 Hz, 1H), 1.84 (t, J=8 Hz, 2H), 1.66 (m, 1H), 0.94 (d, J-7 Hz, 6H); 13 C NMR (75 MHz, CDCl3) delta175.6 (C=O), 49.7 (CH), 37.1 (CH2), 25.7 (CH), 21.7 (CH3). 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, Diethyl isobutylmalonate, other downstream synthetic routes, hurry up and to see. Reference:
Patent; Florida State University; US5470834; (1995); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 57381-43-8, 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 57381-43-8 as follows.

Step 3: Preparation of 5-Bromo-2-r3-cyclopropyl-l-(3-methyl-pyridin-2-yl)-lH-pyrazol-5- ylaminol-benzoic acid methyl ester; To a mixture of 3-cyclopropyl-l-(3-methyl-pyridin-2-yl)-lH-pyrazol-5-amine (1.0 g, 4.667 mmol) and 2,5-dibromo-benzoic acid methyl ester (1.25 g, 4.243 mmol) in toluene (20 mL) was added BINAP (0.264 g, 0.424 mmol), followed by Pd2(dba)3 (0.233 g, 0.255 mmol). To the mixture was added cesium carbonate (1.94 g, 5.94 mmol) and the suspension was heated at 118 ¡ãC overnight and cooled to rt. The cooled reaction mixture was diluted with ethyl acetate and filtered through Celite and concentrated. The product (0.61 g, 31percent) was isolated by column chromatography (25percent ethyl acetate/ hexanes), then on the HPLC (20 to 90 percent acetonitrile). MS m/z 427.1 (M+); HPLC RT (min) 4.06 {method (A)}.

According to the analysis of related databases, 57381-43-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2007/27842; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

18927-05-4, name is Methyl 3-Methoxyphenylacetate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Formula: C10H12O3

[0333] AIBN (10 mg) was added to a solution of (3-Methoxy-phenyl)-acetic acid methyl ester (2g, 11MMOL) in [CCl4] (30ml). The solution was then heated to reflux and NBS (2.3g, 13MMOL) was added in portions. After complete addition the reaction mixture was refluxed for 4h. After cooling, solid residue was filtered off and the filtrate concentrated to yield product BROMO-(3-METHOXY-PHENYL)-ACETIC acid methyl ester, that was washed repeatedly with pet ether.

The synthetic route of 18927-05-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHEMOCENTRYX, INC.; WO2003/105853; (2003); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 50413-30-4, name is Methyl 2-amino-4-methoxylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: Methyl 2-amino-4-methoxylbenzoate

ii. 5-chloro-4-methoxyanthranilic acid (IXc, R=CH3) Treatment of methyl-4-methoxyanthranilate with sulfuryl chloride as described above afforded methyl-4-methoxy-5-chloroanthranilate, M.P., 197-200 C. in 90% yield. Saponification of methyl-4-methoxy-5-chloro anthranilate yielded 5-chloro-4-methoxyanthranilic acid in 64% yield, M.P., 210-3 C. Analysis, Percent Calc’d for C8 H8 ClNO3; C, 47.66; H, 4.00; N, 6.95 Found: C, 48.00; H, 4.11; N, 6.94.

The synthetic route of 50413-30-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; US4287341; (1981); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 130754-19-7, name is Ethyl 2-(4-Chlorophenyl)-2,2-difluoroacetate, 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 130754-19-7, Safety of Ethyl 2-(4-Chlorophenyl)-2,2-difluoroacetate

Part 2. Ethyl 4-chlorophenyl-2,2-difluoroacetate (250 mg) and potassium hydroxide (300 mg) were mixed in 27 ml of ethanol and 2.4 ml of water and the reaction mixture was refluxed for four hours. The mixture was then acidified and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous Na2 SO4 and the solvent was removed in vacuo to give a product which was dissolved in 410 mg of oxalyl chloride with catalytic amount of N,N-dimethylformamide. The mixture was stirred for two hours and excess oxalyl chloride was removed in vacuo to give 4-chlorophenyl-2,2-difluoroethanoyl chloride which was used as is for the subsequent step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 2-(4-Chlorophenyl)-2,2-difluoroacetate, and friends who are interested can also refer to it.

Reference:
Patent; The Dupont Merck Pharmaceutical Company; US5583147; (1996); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 145576-28-9, 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. 145576-28-9, name is Ethyl 4-methylenecyclohexanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Cap N-8 At 0 C., to a solution of ethyl 4-methylenecyclohexanecarboxylate (0.08 g) in DCE (1 mL) was added chloroiodomethane (0.110 mL, 1.522 mmol), followed by the addition of 1 N diethylzinc in hexane (0.761 mL, 0.761 mmol). The reaction was stirred at 0 C. for 1 hr, then stirred at rt for 18 hrs. The reaction mixture was diluted with EtOAc and 1 N HCl, the organic phase was washed with sat. NaCl, dried over anhydrous Na2SO4, filtered and concentrated. The crude product was charged to a 25 g silica gel cartridge which was eluted with a 20 min gradient of 0-6% EtOAc in hexane to yield ethyl spiro[2.5]octane-6-carboxylate. 1H NMR (400 MHz, CDCl3) delta ppm 4.08-4.18 (2H, m), 2.32 (1H, tq, J=11.01, 3.53 Hz), 1.85-1.93 (2H, m), 1.53-1.74 (4H, m), 1.28-1.35 (2H, m), 1.22-1.28 (3H, m), 0.28 (2H, ddd, J=8.53, 5.52, 1.51 Hz), 0.17-0.25 (2H, m).

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

Reference:
Patent; Bristol-Myers Squibb Company; Hewawasam, Piyasena; Kadow, John F.; Lopez, Omar D.; Meanwell, Nicholas A.; Tu, Yong; Wang, Alan Xiangdong; Xu, Ningning; Gupta, Samayamunthula Venkata Satya Arun Kumar; Srinivasu, Pothukanuri; Kumar, Indasi Gopi; Kumar, Ponugupati Suresh; Belema, Makonen; Fridell, Robert A.; Gao, Min; Lemm, Julie A.; O’Boyle, II, Donald R.; Sun, Jin-Hua; Wang, Chunfu; Wang, Ying-Kai; US2013/183269; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 369-26-6,Some common heterocyclic compound, 369-26-6, name is Methyl 3-amino-4-fluorobenzoate, molecular formula is C8H8FNO2, 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.

Intermediate 37: 2-Propen-1-yl {5-[(2-chloro-4-pyrimidinyl)acetyl]-2-fluorophenyl}carbamate; Step A: Methyl 4-fluoro-3-{[(2-propen-1-yloxy)carbonyl]amino}benzoate; To a solution of methyl 3-amino-4-fluorobenzoate (109 g, 644 mmol) in THF (2000 mL), saturated NaHCO3 (68 g, 805 mmol) was added. Then 2-propen-1-yl chloridocarbonate (93 g, 773 mmol) was added dropwise at 0 C. The mixture was stirred at rt for 2 h. The solution was extracted with EtOAc (500 mL¡Á3). The combined organic layers were washed with water and brine successively, dried over Na2SO4, filtered and concentrated under reduced pressure to give the crude product (160 g, 98%), which was used in the next step directly. 1H NMR (400 MHz, CDCl3) delta ppm 8.72-8.81 (m, 1H), 7.71-7.79 (m, 1H), 7.09-7.16 (m, 1H), 6.87-6.94 (br, 1H), 5.91-6.03 (m, 1H), 5.41 (d, J=17.1 Hz, 1H), 5.28 (d, J=10.5, 1H), 4.70 (d, J=10.5 Hz, 1H), 4.70 (d, J=5.5 Hz, 2H), 3.90 (s, 3H).

The synthetic route of 369-26-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Adams, Jerry Leroy; Dickerson, Scott Howard; Johnson, Neil W.; Kuntz, Kevin; Petrov, Kimberly; Ralph, Jeffrey M.; Rheault, Tara Renae; Schaaf, Gregory; Stellwagen, John; Tian, Xinrong; Uehling, David Edward; Waterson, Alex Gregory; Wilson, Brian; US2009/298815; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 39149-80-9, name is tert-Butyl 2-bromopropanoate, 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 39149-80-9, Computed Properties of C7H13BrO2

(1) Preparation of 2-(quinolin-5-yloxy)propanoic acid (A01): Quinolin-5-ol (0.868 g, 5.98 mmol) and tert-butyl 2-bromopropanoate (1.25 g, 0.97 mL, 5.98 mmol) and cesium carbonate (1.95 g, 5.98 mmol) were added into DMF (10 mL) in a 20 mL microwave vial equipped with a stir bar and sealed. The mixture was heated in Biotage microwave synthesizer for 1 hour at 100 C. The solvent was removed and the remained sticky oil was dissolved in DCM (7 mL) and TFA (7 mL). The mixture was stirred overnight. The reaction mixture was neutralized with sodium bicarbonate and organic layer was separated from the mixture. The aqueous layer washed with DCM (2*10 mL), combined organics and acidified with 2N HCl. Aqueous was extracted with ethyl acetate, dried with sodium sulfate and concentrated to a dark orange oil. The crude product was dissolved in DCM (4 mL) and a pure product (0.855 g) precipitate out from the solution by adding diethyl ether (4 mL).

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, tert-Butyl 2-bromopropanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/287730; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 42122-44-1,Some common heterocyclic compound, 42122-44-1, name is Methyl 3-(4-fluorophenyl)propiolate, molecular formula is C10H7FO2, 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.

c Methyl 2-(4-fluorophenyl)-pyrazolo[1,5-a]pyridine-3-carboxylate A stirred solution of methyl 3-(4-fluorophenyl)propiolate (8.02 g, 45 mmol) and 1-aminopyridinium iodide (10 g, 45 mmol) in dry acetonitrile (150 mL) was cooled to about 0 C. A solution of 1,8-diazabicycloundec-7-ene (13.7 g, 90 mmol) in dry acetonitrile (50 mL) was added dropwise over 1 h. The mixture was allowed to stir at room temperature for about 18 h. The reaction mixture was cooled in an ice bath for about 30 min and the precipitate was collected by filtration and washed with cold acetonitrile (10 mL). The solid was dried under reduced pressure to give the title compound as a white solid, 8.48 g (70%). 1H NMR (CDCl3) delta 8.50 (d, 1H, J=8.4 Hz), 8.18 (d, 1H, J=8.8 Hz), 7.78 (m, 2H), 7.42 (t, 1H, J=8.4 Hz), 7.13 (t, 2H, J=8.8 Hz), 6.97 (td, 1H, J=6.8, 1 Hz). MS (+ve ion electrospray) 271 (100), (MH+).

The synthetic route of 42122-44-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Alberti, Michael John; Baldwin, Ian; Cheung, Mui; Cockerill, Stuart; Harris, Philip; Jung, David; Peckham, Gregory; Peel, Michael; Badiang, Jennifer; Stevens, Kirk; Veal, James; US2004/53942; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics