Month: August 2021

Some common heterocyclic compound, 20754-20-5, name is Methyl 3-(p-tolyl)acrylate, molecular formula is C11H12O2, 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 Methyl 3-(p-tolyl)acrylate

A method for constructing a quaternary carbon ring by visible light catalysis [2+2] reaction, comprising the following steps: The ruthenium complex 1 was used as a visible light catalyst, and 1.3 mg of the catalyst and 0.2 mmol were added to 2 mL of 1,4-dioxane.(E)-methyl-3-p-tolyl acrylate(corresponding R2 is p-tolyl and R3 is methoxy), wherein the concentration of the visible light catalyst is 1.0 x 10-3 M. Argon gas was introduced for ten minutes, and then light-illuminated in an argon atmosphere at 25 ° C for 36 hours with Blue LEDs of 450 nm ± 10 nm. After the reaction was completed, the mixture was directly dried and separated by column. Nuclear magnetic resonance, carbon, and mass spectrometry identify products as racemic(1R, 2R, 3S, 4S)-dimethyl-3,4-di-p-methylphenylcyclobutane-1,2-dicarboxylate. The conversion of the starting material was 100percent and the yield of the cyclobutane product was 90percent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 20754-20-5, its application will become more common.

Reference:
Patent; Chinese Academy Of Sciences Physics And Chemistry Technology Institute; Wu Lizhu; Lei Tao; Zhao Leimin; Zhou Chao; Liu Zan; Tong Zhenhe; (89 pag.)CN108623425; (2018); A;,
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Application of 4630-82-4,Some common heterocyclic compound, 4630-82-4, name is Methyl cyclohexanecarboxylate, molecular formula is C8H14O2, 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.

General procedure for the catalytic hydrogenation of methyl benzoate as substrate: Under argon, a Keim autoclave was charged with [Ru Cl2(R-BINAP)(dm02] (0.01 mmol, 0.05 mol %) and S,S-DPEN (0.01 mmol, 0.05 mol %) followed by THF (2 ml) and the solution stirred for 5 minutes. Then a solution of the desired ester (20 mmol) in THF (2 ml), followed by more THF (2×1 ml), and a solution of tridecane (1 mmol) in THF (2 ml), as internal standard, followed by more THF (2×1 ml), were successively added to the autoclave. Finally, solid NaOMe (1 mmol, 5 mol %) was added and the autoclave was pressurised with hydrogen gas at 50 bars and placed in a thermostatted oil bath set at 60 C. After the mentioned time, the autoclave was removed from the oil bath, and cooled in a cold-water bath. Then, an aliquot (0.4 ml) was taken, diluted with MTBE (5 ml), washed with aq. sat. NH4Cl (5 ml), and filtered over a plug of celite and analyzed by GC.

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

Reference:
Patent; Saudan, Lionel; Saudan, Christophe; Saudan, Michel Alfred Joseph; Saudan, Sylvia Joyeuse Adelaide Ada; US2010/286452; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 22223-49-0, name is Methyl 2-amino-3-methylbenzoate, 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 22223-49-0, Recommanded Product: Methyl 2-amino-3-methylbenzoate

A solution of methyl 2-amino-3-methylbenzoate (142.1 g, 0.843 mol, purity: 98% quantitative NMR) in 240 mL of H2O is gradually admixed at 30 C. with hydrogen bromide (48% of H2O, 149.2 g, 0.885 mol) added dropwise. The suspension obtained is admixed with hydrogen peroxide (30% in H2O, 105.1 g, 0.927 mol) added dropwise over 2 h, and the temperature is kept below 70 C. After 1 hour of subsequent stirring, NaHSO3 (39% in H2O, 33.7 g, 0.126 mol) is added a little at a time (peroxide test was negative). The suspension obtained is adjusted to pH7-8 with Na2CO3 (0.1 eq., 9.0 g, 0.084 mol), which is added a little at a time. Following filtration and drying in a vacuum drying cabinet, methyl 2-amino-5-bromo-3-methylbenzoate is isolated as a pale brown solid. Yield: 204.2 g, 97.7% of theory, purity: 98.5% quantitative NMR). 1H NMR (600 MHz, (d6-DMSO): delta=7.70 (d, 1H), 7.36 (pt, 1H), 6.63 (br s, 2H), 3.80 (s, 3H), 2.12 (s, 3H)).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-amino-3-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Volz, Frank; Himmler, Thomas; Mueller, Thomas Norbert; Lehmann, Sandra; Von Morgenstern, Sascha; Moradi, Wahed Ahmed; Pazenok, Sergii; Lui, Norbert; US2014/148611; (2014); A1;,
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Ester – an overview | ScienceDirect Topics

Electric Literature of 773134-11-5, These common heterocyclic compound, 773134-11-5, name is Methyl 4-bromo-2,6-difluorobenzoate, 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.

To a 25 mL round-bottom flask was added methyl4-bromo-2,6-difluorobenzoate104h (160 mg, 0.64 mmol, 1.2 equiv.), (1S,4S,5R)-5-[5-cydopropyl-3-(2,6-dichlorophenyl)L2-oxazol-4-yl]methoxy-2-azabicyclo[2.2.1]heptane 12dd (200 mg, 0.394 mmol, 1.0 equiv.),25 Pd(OAc)2 (60 mg, 0.27 mmoL 0.69 equiv.), Xantphos (150 mg, 0.26 mmol, 0.66 equiv.),Cs2C01 (340 mg, 1.04 mmol, 2.64 equiv.), and toluene (4 mL). The resulting mixture was stirred at 90C overnight. Upon cooling, the mixture v.·as diluted vvith 20 mL ofi-bO andextracted with ethyl acetate (20 mL x 2). The combined organic extracts vvere washed withVater (20 mL x 2), dried over anhydrous sodium sulfate and concentrated under vacuum. Theresidue was purified by silica gel colunm chromatography eluting with ethyl5 acetate/petroleum ether (1 :5) to give 4-[(lS,4S,5R)-5-[[5-cyclopropy-3-(2,6-dichlorophenyl)-1 ,2-oxazol-4-yl]methoxy ]-2-azabicyclo[2.2.1 ]heptan-2-yl]-2,6-difluorobenzoate l04c (26 mg, 12.31()) as a yellow oil.

The synthetic route of 773134-11-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (582 pag.)WO2018/39386; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, 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 924-99-2, Product Details of 924-99-2

[1311] to a solution of ethyl 3-(dimethylamino)acrylate (165 mg, 1.2 mmol) and tea (233 mg, 2.3 mmol) in THF (15 ml) was added a solution of compound 277b (400 mg, 2.3 mmol) in THF (5 ml) drop-wise over 30 mins. The mixture was stirred at 20 C for 12 hours. The reaction mixture was concentrated under reduced pressure to give a residue. The residue was purified by preparatory-tlc (SiO2, petroleum ether: ethyl acetate = 1: 1) to give compound 277c (240 mg, yield: 44.4%) as a pale yellow oil. 1H NMR (400mhz, CDCl3) delta 8.94 (s, 1h), 7.51 – 7.36 (m, 2h), 7.21 – 7.14 (m, 1h), 7.13- 7.04 (m, 1h), 4.17 (q, 7 = 7.1 hz, 2h), 1.15 (t, 7 = 7.2 hz, 3h).

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; BLADE THERAPEUTICS, INC.; BUCKMAN, Brad, Owen; YUAN, Shendong; ADLER, Marc; EMAYAN, Kumaraswamy; MA, Jingyuang; (687 pag.)WO2018/64119; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 37746-78-4, 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 37746-78-4 as follows.

To a solution of ethyl 4-bromocrotonate 23 (0.9 mL, 5.18 mmol) in anhydrous dioxane (10 mL), palladium triphenyl phosphine tetrakis (300 mg, 0.26 mmol) was added to the round bottom flask. The flask was then evacuated three times at rt and backfilled with argon. The reaction mixture was allowed to stir for 15 min at rt then phenyl boronic acid (1.84 g, 10.36 mmol) and Na2CO3 (2.75 g, 25.9 mmol) were added under a positive pressure of argon. The reaction mixture which resulted was heated at reflux for 18 h and then cooled to rt. It was then passed through a short bed of celite. The celite bed was washed with EtOAc (50 mL) and the combined organic layers were washed with water (50 mL) and brine (30 mL). The organic layer was dried (Na2SO4) and concentrated under reduced pressure. The crude oil was purified by flash column chromatography (5% EtOAc in hexanes) on silica gel to afford ester 18 (893 mg, 70%). 1H NMR (300 MHz, CDCl3): delta 7.37 (d, J = 8.1 Hz, 2H), 7.14 (d, J = 7.8 Hz, 2H), 7.12 (d, J = 15.6 Hz, 1H), 5.85 (d, J = 15.3 Hz, 1H), 4.21 (q, J = 7.2 Hz, 2H), 3.52 (d, J = 6.9 Hz, 2H), 1.35 (S, 9H), 1.31 (t, J = 6.9 Hz, 3H); 13C NMR (75 MHz, CDCl3): delta 166.5, 149.6, 147.5, 134.7, 128.5, 125.6, 122.2, 60.2, 38.0, 34.4, 31.4, 14.3. HRMS (ESI) (M+Na)+, calcd for C16H22O2Na 269.1518; found 269.1512.

According to the analysis of related databases, 37746-78-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Tiruveedhula, V.V.N. Phani Babu; Witzigmann, Christopher M.; Verma, Ranjit; Kabir, M. Shahjahan; Rott, Marc; Schwan, William R.; Medina-Bielski, Sara; Lane, Michelle; Close, William; Polanowski, Rebecca L.; Sherman, David; Monte, Aaron; Deschamps, Jeffrey R.; Cook, James M.; Bioorganic and Medicinal Chemistry; vol. 21; 24; (2013); p. 7830 – 7840;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 88709-17-5 as follows. Recommanded Product: Ethyl 2-ethoxy-4-methylbenzoate

00465] Step 2: Synthesis of ethyl 4-(bromomethyl)-2-ethoxybenzoate: To a solution of ethyl 2-ethoxy-4-methylbenzoate (100 mg, 0.481 mmol) in 2 mL oftrifluoromethyl toluene was added NBS (94 mg, 0.529 mmol) and AIBN (10 mg) in portions. The mixture was heated to reflux and stirred for 24 h. The reaction mixture was concentrated, diluted with 10 mL of EA, washed with 5 mL of 4 N NaOH, 5 mL of brine, dried over anhydrous Na2S04 and concentrated under reduced pressure to afford ethyl 4-(bromomethyl)- 2-ethoxybenzoate as brown oil (42 mg, 30%), which was used for the next step directly.

According to the analysis of related databases, 88709-17-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; N30 PHARMACEUTICALS, LLC; SUN, Xicheng; QIU, Jian; WO2011/38204; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 55666-43-8, name is tert-Butyl 3-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 55666-43-8, Recommanded Product: tert-Butyl 3-bromopropanoate

Cyclohexanecarboxylic acid (2.89 g, 22.6 mmol) was dissolved in THF (30 mL) and this solution added to a lithium diisopropylamide solution cooled to -15 C. (2M in THF/n-heptane/ethylbenzene, Aldrich) 24.3 mL (48.6 mmol) at such a rate as to keep the temperature below 0 C. The reaction mixture was then stirred at 0 C. for 2.5 hours before re-cooling to -15 C. and the addition of tert-butyl 3-bromopropionate (5 g, 23.9 mmol) in THF (50 mL) at such a rate as to keep the temperature below 0 C. The reaction mixture was allowed to reach room temperature and stirred overnight, before the reaction mixture was quenched by the addition of 2M HCl and extracted with ethyl. acetate 2×200 mL. The combined organic layers were dried (MgSO4) and then evaporated to an orange oil. Purification by flash chromatography [SiO2; dichloromethane/methanol/0.880 NH3 (97:3:0.5)] afforded the title compound as a gummy oil (800 mg, 14%). 1H NMR (CDCl3, 400 MHz), deltaH: 2.22 (2H, m), 2.07-2.00 (2H, m), 1.86 (2H, m), 1.45-1.16 (8H,m), 1.41 (9H, s): m/z (ES+) 279(MNa+); m/z (ES-) 255 M-H+)

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 3-bromopropanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pfizer Inc; US2004/180941; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 106896-49-5, The chemical industry reduces the impact on the environment during synthesis 106896-49-5, name is Methyl 4-amino-3-bromobenzoate, I believe this compound will play a more active role in future production and life.

To a 1L rmmd-boitom t1ask purged with and rnaintained under an inert atrnosphere of.5 nitrogen vvas added methyl 4-amino-3-bromobenzoate 249a (13.6 g, 59.12 mmol, 1.00equiv.), (furan-3-yl)boronic acid (10 g, 89.37 mmol, 1.50 equiv.), 1,4-dioxane (500 mL), 1Maq. NaHC01 (17.5 g, 3.50 equiv.), and tetrakis(triphenylphosphine) palladium (6.86 g, 5.94mmol, 0.10 equiv.). The resulting mixture was heated at ll (J”C overnight vvith stirring. Aftercooling to room temperature, the mixture was diluted with 200 mL of water, and extracted10 with ethy 1 acetate (500 mL x 2). The combined orga.nic extracts were washed successivelywith t-hO (500 mL) and brine (500 mL x 2), dried over anhydrous sodium sulfate, andconcentrated under vacuum The crude product was purified by Flash-Prep-HPLC using thefollowing conditions (lntelFlash-1 ): Colunm, silica gel; mobile phase: EA: PE=O: 100increasing toEA: PE'”50:50 within 20 min; Detector, UV 254 nm. Removal of sol vents gavel 5 methyl 4-amino-3-(furan-3-yl)benzoate 25 l a (8.345 g, 65%) as a yellow oil.

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-bromobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (582 pag.)WO2018/39386; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 40872-87-5, These common heterocyclic compound, 40872-87-5, name is Methyl 3-amino-4-chlorobenzoate, 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.

It heated and dried at 120 degrees C under decompression of a p-toluenesulfonic-acid monohydrate (25.6g) for 1 hour. The methyl 3-amino-4-chlorobenzoate (10g) and the propiononitrile (20 ml) were added there, and it heated at reflux for 16 hours. After cooling a reaction mixture radiationally, the saturated sodium bicarbonate aqueous solution (250 ml) was added, and it stirred for 10 minutes. Ethyl acetate extracted, after carrying out decompression distilling off of the propiononitrile (50mlx3). The organic layer was dried and concentrated in vacuum with anhydrous sodium sulfate. Silica gel column chromatography (developing solvent: petroleum ether/ethyl acetate) refined the obtained residue, and it obtained the mark compound (8.5g).

The synthetic route of 40872-87-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUMITOMO DAINIPPON PHARMA COMPANY LIMITED; IKEDA, JUNYA; NAKAMURA, TAKANORI; OTAKA, HIROMICHI; (133 pag.)JP2016/28016; (2016); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics