Month: January 2021

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. 2216-94-6, name is Ethyl phenylpropiolate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Ethyl phenylpropiolate

General procedure: The reaction was performed in a 20-mL round-bottomed flask equipped with a Teflon-coated magnetic stirrer bar. A solution of Pd(TPP) (3.6 mg, 0.005 mumol) and DMAP (0.01 mmol, 1.2 mg) in pyridine (1 mL) was stirred at 25 C for 0.5 h under H2(1 atm, balloon). A soln of alkyne 1(0.5 mmol) in pyridine (4 mL) was added,and the mixture was stirred for the indicated time. H2O (20 mL) was added, and the aqueous phase was extracted with EtOAc (3 ¡Á 50 mL). The organic phases were combined, dried (Na2SO4), and concentrated in vacuo. The residue was purified by flash column chromatography [silica gel (20 g, 2 ¡Á 15 cm), hexane-EtOAc (40:1)] to give an alkene 2.

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 2216-94-6.

Reference:
Article; Nishibayashi, Ryo; Kurahashi, Takuya; Matsubara, Seijiro; Synlett; vol. 25; 9; (2014); p. 1287 – 1290;,
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Synthetic Route of 52727-57-8, A common heterocyclic compound, 52727-57-8, name is Methyl 2-amino-5-bromobenzoate, molecular formula is C8H8BrNO2, 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.

Example 54; 2-Amino-5-(2-11-[(4-aminomethyl-cyclohexanecarbonyl)-aminol-2-phenyl-ethyll- pyridin-4-yl)-benzoic acid methyl ester, tris-trifluroacetic acid salt; [00404] 54A. 2-Amino-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-benzoic acid methyl ester: To a flame-dried, round-bottom flask equipped with a condenser was added 2-Amino-5-bromo-benzoic acid methyl ester (0.7 g, 3.0 mmol), Pd (dppf)Cl2No.CH2Cl2 complex (0.106 g, 0.130 mmol), KOAc (1.28 g, 13.0 mmol), and bis(neopentyl glycolato) diboron (1.08 g, 4.78 mmol). Next degassed DMSO (29 mL) was added and the reaction was stirred at 80 C. After 5 h, the reaction was cooled to rt, diluted with EtOAc (100 mL), washed with water, brine, dried over Na2S04, filtered and concentrated. Column chromatography on silica gel (gradient elution 0- 20% EtOAc/Hexane) gave 54A (0.858 g, 75%) as a white solid. ?H NMR (400 MHz, CDC13) 8: 1.01 (s, 6 H), 3.74 (s, 4 H), 3.86 (s, 3 H), 5.91 (bs, H), 6.63 (d, J = 8.3 Hz, 1 H), 7.66-7.68 (m, 1 H), 8.33 (s, 1 H). MS 196.1 (M – C5H8 + H)+.

The synthetic route of 52727-57-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2005/123680; (2005); A1;,
Ester – Wikipedia,
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Reference of 457097-93-7, 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. 457097-93-7, name is Methyl 4-amino-3-(trifluoromethoxy)benzoate, This compound has unique chemical properties. The synthetic route is as follows.

[Step 1] 4-[(Ethylsulfonyl)amino]-3-(trifluoromethoxy)benzoic acid Using methyl 4-amino-3-(trifluoromethoxy)benzoate (300 mg) and ethanesulfonyl chloride (0.724 ml), synthesis was carried out in the same manner as in Step 1 of Example 8 to obtain the title compound (408 mg) as a solid. 1H-NMR (DMSO-D6) delta: 1.25 (3H, t, J=7.3 Hz), 3.27 (2H, q, J=7.3 Hz), 7.69 (1H, d, J=9.2 Hz), 7.80-7.84 (1H, m), 7.91 (1H, dd, J=8.5, 1.8 Hz), 10.27 (1H, s), 13.31 (1H, br s). MS (ESI/APCI) m/z: 312 [M-H]-

The chemical industry reduces the impact on the environment during synthesis Methyl 4-amino-3-(trifluoromethoxy)benzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Daiichi Sankyo Company, Limited; Ota, Masahiro; Inoue, Hidekazu; Kawai, Junya; Ohki, Hitoshi; Toki, Tadashi; (25 pag.)US2019/284198; (2019); A1;,
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Reference of 711-01-3, These common heterocyclic compound, 711-01-3, name is Methyl adamantane-1-carboxylate, 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.

Under a nitrogen atmosphere, 30.5 g (4.4 mol) of lithium metal (Li) was added to 2 L of tetrahydrofuran (THF) and stirred for 1 hour.Into this, a solution of 300 g (2.0 mol) of 2-adamantanone and 258.0 g (3.3 mol) of 2-chloropropane dissolved in 1000 mL of THF was added dropwise over 30 minutes while cooling so as to keep 20 ¡ã C. or less. .After completion of the dropwise addition, the mixture was stirred at 20 ¡ã C. for 90 minutes to obtain a THF solution of lithium 2-isopropyl-2-adamantyl alcoholate.To this THF solution, 362.0 g (2.4 mol) of methacrylic anhydride was added dropwise over 15 minutes while cooling so as to keep 20 ¡ã C. or less.After completion of the dropwise addition, the mixture was stirred at 20 ¡ã C. for 60 minutes to synthesize 2-isopropyl-2-adamantyl methacrylate.After completion of the reaction, 4 L of toluene was added, and further 2000 mL of 0.2 N aqueous NaOH solution was added, and the mixture was stirred at 20 ¡ã C. for 60 minutes.After removing the aqueous phase, washing was performed twice with 2 L of pure water.The solvent was distilled off from the organic phase to obtain 517.0 g of crude 2-isopropyl-2-adamantyl methacrylate (crude yield: 99percent, GC purity: 84.9percent).Subsequently, 0.7 g of p-methoxyphenol as a polymerization inhibitor is added to the obtained crude 2-isopropyl-2-adamantyl methacrylate,While distilling dry air from the capillary, carry out simple distillation at 0.1 kPa and 100 to 120 ¡ã C,369.0 g of distilled 2-isopropyl-2-adamantyl methacrylate (GC purity 88.2percent, referred to as ?distillate B?) was obtained.

The synthetic route of 711-01-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Osaka Organic Chemical Industry Ltd.; Kojima, Akio; Kono, Naoya; Uenoyama, Yoshitaka; (20 pag.)JP6478447; (2019); B2;,
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Related Products of 54535-22-7, These common heterocyclic compound, 54535-22-7, name is Diethyl 2-((phenylamino)methylene)malonate, 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 I 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 Na2C03 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; HASELTINE, Eric L.; MOSKOWITZ, Samuel; ROBERTSON, Sarah; WALTZ, David; (169 pag.)WO2019/18395; (2019); A1;,
Ester – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 84228-44-4, name is Methyl 4-amino-3-chlorobenzoate, 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 84228-44-4, Recommanded Product: 84228-44-4

To a solution of methyl 4-amino-3-chlorobenzoate (0.37g, 0.002 mol) and diisopropylethylamine (0.39g, 0.003 mole) in dioxane at ambient temperature was added in one portion 2-oxo-l ,2-dihydro-3-pyridinecarbonyl chloride (0.4g, 0.002 mol) [prepared as described in WO/201 1/088201 Al]. The mixture was heated at reflux for 24 h. after which it was cooled to ambient temperature and partitioned between EtOAc and water. The two phase material was filtered and the solid was washed with water, then EtOAc and air dried to obtain a 25% yield of the title compound as an off-white solid. MS: m z 305 (MIT) and m/z 307 (MH+). NMR (500 MHz, DMSO-d6): delta 3.848 (s, 3H), 6.604 (t, 1H), 7.878 (qd, 1H), 7.942 (dd, 1H), 8.015 (d, 1H), 8.504 (dd, 1H), 8.744 (d, 1H), 12.787 (br s, 1H), 12.893 (s, 1H).

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, Methyl 4-amino-3-chlorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NORTH CAROLINA CENTRAL UNIVERSITY; THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; SEXTON, Jonathan Z.; BRENMAN, Jay E.; WO2014/165816; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 23426-63-3, name is Methyl 2-bromo-2-methylpropanoate, molecular formula is C5H9BrO2, 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. Quality Control of Methyl 2-bromo-2-methylpropanoate

A 12 L, 3 neck round bottom flask equipped with a mechanical stirrer, thermometer, condenser and nitrogen bubbler, was charged with malononitrile (251 g, 3.802 moles) and THF (2 liters). Potassium t-butoxide (1M THF, 3.802L, 3.802 moles) was then added. The mixture was stirred at 50C for 30 min. Methyl 2-bromoisobutyrate (688 g, 3.80 moles) was added and the reaction mixture was stirred overnight at 50C. The reaction was partitioned between aqueous 1 N HCI and EtOAc. The organic phase was washed with brine, dried over MgSO4, filtered, and concentrated to give the title product. 1H NMR (400 MHz, CD3CN): delta 4.35 (1 H, s) 3.73 (3 H, s), 1.43 (6 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 23426-63-3, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; HAN, Xiaoqing; WHITEHEAD, Alan; RAGHAVAN, Subharekha; CERNAK, Timothy, A.; DREHER, Spencer; GROEPER, Jonathan; GUO, Jian; ZHANG, Yong; WO2015/88886; (2015); A1;,
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Synthetic Route of 1014645-87-4,Some common heterocyclic compound, 1014645-87-4, name is Methyl 4-(1-aminocyclopropyl)benzoate hydrochloride, molecular formula is C11H14ClNO2, 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 solution of (3R)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid (syn-anti diastereoisomer mixture 10/2) (D27) (3.06 g, 13.5 mmol) in dry DMF (15 ml) under N2 atmosphere HOBT.H2O (2.06 g, 13.46 mmol), EDC.HCl (3.87 g, 20.20 mmol), methyl 4-(1-aminocyclopropyl)benzoate hydrochloride (3.06 g, 13.46 mmol) and TEA (4.7 ml, 33.7 mmol) were added in sequence. The mixture was stirred for 2 hrs at RT, then the solvent was evaporated in vacuo and the residue taken up in AcOEt (500 ml), washed twice with water (50 ml), dried over Na2SO4 and evaporated to afford a residue which was loaded on a SNAP-Si cartridge (100 g) and eluted with a mixture DCM/AcOEt from 10/0 to 9/1. Collected fractions after solvent evaporation afforded the two diastereoisomer (D73a) (2.55 g) and (D73b) (880 mg).(D73a) (syn diastereoisomer)MS: (ES/+) m/z: 401.4 [MH+] C22H28N2O5 requires 400.201H NMR (400 MHz, DMSO-d6) delta (ppm): 8.70 (s, 1H), 7.90-7.76 (m, 2H), 7.34-7.19 (m, 2H), 4.52-4.35 (m, 1H), 3.84 (s, 3H), 3.43-3.32 (m, 1H), 2.67-2.39 (m, 1H), 1.88-1.74 (m, 1H), 1.52-1.33 (m, 10H), 1.27-1.12 (m, 4H), 1.09-0.92 (m, 1H), 0.66-0.53 (m, 1H).(D73b) (anti diastereoisomer)MS: (ES/+) m/z: 401.4 [MH+] C22H28N2O5 requires 400.201H NMR (400 MHz, DMSO-d6) delta (ppm): 8.69-8.52 (s, 1H), 7.90-7.73 (m, 2H), 7.35-7.19 (m, 2H), 3.93-3.75 (m, 4H), 3.36-3.30 (m, 1H), 2.35-2.19 (m, 1H), 2.12-2.02 (m, 1H), 1.90-1.74 (m, 1H), 1.47-1.30 (m, 9H), 1.25-1.07 (m, 4H), 0.73 (td, J=5.4, 8.8 Hz, 1H), 0.39 (br. s., 1H).

The synthetic route of 1014645-87-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Borriello, Manuela; Pucci, Sabrina; Stasi, Luigi Piero; Rovati, Lucio; US2015/87626; (2015); A1;,
Ester – Wikipedia,
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Synthetic Route of 58656-98-7, 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 58656-98-7 as follows.

A Preparation of (26) where R10 is 2-Cyanoindole A mixture of 3.0 g (0.02 mol) of 2-cyanoindole, 4.2 g (0.02 mol) of tert-butyl-4-fluorobenzoate, and 5.5 g (0.04 mol) of potassium carbonate in 30 ml dimethyl sulfoxide was heated at 110 C. for 48 hours. The reaction was poured onto ice-water and extracted twice with ethyl acetate. The organic extracts were combined, washed with water and dried over magnesium sulfate. Evaporation yielded a dark oil which was flash chromatographed on silica gel, eluding with ethyl acetate-hexane 1:9 to give 3.6 g (0.011 mol) of 1-[4-(tertbutoxycarbonyl)phenyl]-2-cyanoindole as an oil.

According to the analysis of related databases, 58656-98-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Syntex (U.S.A.) Inc.; US5380739; (1995); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 7149-03-3, A common heterocyclic compound, 7149-03-3, name is Ethyl 4-amino-3-bromobenzoate, molecular formula is C9H10BrNO2, 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.

Compound 11b (11.8 g, 48.34 mmol) was dissolved in concentrated hydrochloric acid (60.43 mL, 12N) at -10C, then a solution of sodium nitrite (4.00 g, 58.01 mmol) in water (300 mL) was added dropwise. The resulting reaction solution was reacted at 0C for 0.5 hour, and added at -10C in portions to another reaction vessel containing cuprous chloride (1.44 g, 14.50 mmol) and liquid sulfur dioxide (9.29 g, 145.03 mmol). . The resulting reaction solution was reacted at 0C for 0.5 hours. After extraction with ethyl acetate (100 mL¡Á3), the organic phase was washed with saturated brine (100 mL¡Á3), dried over anhydrous sodium sulfate, filtered, and concentrated to give compound 11c (14.00 g).

The synthetic route of 7149-03-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhengda Tianqing Pharmaceutical Group Co., Ltd.; Nanjing Mingde Drug Discovery Co., Ltd.; Yao Yuanshan; Chen Bin; Chen Yuan; Li Ao; Xu Ran; Huang Zhensheng; Tian Dongdong; Li Hongwei; Yang Chengshuai; Li Jian; Chen Shuhui; (26 pag.)CN107987072; (2018); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics