Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 17100-65-1, name is Methyl 2-bromo-4-methoxybenzoate, 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 17100-65-1, HPLC of Formula: C9H9BrO3

A mixture of methyl 2-bromo-4- methoxybenzoate (4) (5.9 g, 23.9 mmol), butyl vinyl ether (15.4 mL, 119.4 mmol), Ph3P (939.0 mg, 3.6 mmol), Et3N (4.3 mL, 31.0 mmol), and Pd(OAc)2 (343.0 mg, 1.8 mmol) in MeCN (45 mL) is stirred under argon at 97 C for 18 h, cooled to room temperature, diluted with H2O (50 mL), and filtered through Celite (H2O rinse). The filtrate is concentrated to dryness at reduced pressure. The residue plus tetrahydrofuran (140 mL) and 10% HCl (140 mL) were stirred for 2 h. After tetrahydrofuran removal at reduced pressure, the residue is extracted with dichloromethane (3 x 70 mL). The extract is washed (brine) and dried. After solvent removal at reduced pressure, the residue is purified on silica gel (16.7% to 33.3% ethyl acetate/hexane) to give 4.8 g (96%) of 5 as a yellow solid, mp 48-50 C. IR 2962, 1733, 1688, 1258 cm”1; 1HNMR (CDCl3) delta 2.50 (s, 3H, CH3CO), 3.86 (s, 6H, CH3O, CO2CH3), 6.76 (d, J= 2.0 Hz, IH, 3-PhH), 6.93 (dd, J= 7.2, 2.0 Hz, IH, 5-PhH), 7.90 ppm (d, J= 7.2 Hz, IH, 6-PhH).

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 2-bromo-4-methoxybenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BURNHAM INSTITUTE FOR MEDICAL RESEARCH; MERCOLA, Mark; DAWSON, Marcia, I.; CASHMAN, John; WO2010/33643; (2010); A2;,
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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. 609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 609-12-1

Example 18 A mixture of (2-hydroxy-4-methoxyphenyl){4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl}methanone (400 mg), ethyl 2-bromo-3-methylbutanoate (302 mg), potassium carbonate (226 mg) and N,N-dimethylformamide (3 ml) was stirred at room temperature for 15 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, eluted with ethyl acetate-hexane (1:4?1:1, v/v), and concentrated. The residue was dissolved in tetrahydrofuran (6 ml), ethanol (4 ml), water (4 ml) and lithium hydroxide monohydrate (116 mg) were added, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was neutralized with dil. hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate layer was washed with water and saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, eluted with ethyl acetate-hexane (1:3?3:1, v/v), concentrated, and crystallized from ethyl acetate-hexane to give 2-(5-methoxy-2-{4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzoyl}phenoxy)-3-methylbutanoic acid (382 mg, yield 77%) as colorless crystals. melting point 87 – 88C. 1H-NMR (300 MHz, CDCl3) delta:1.06 (3 H, d, J=6.9 Hz), 1.14 (3 H, d, J=6.9 Hz), 2.36 – 2.46 (1 H, m), 2.47 (3 H, s), 3.86 (3 H, s), 4.85 (1 H, d, J=3.6 Hz), 5.10 (2 H, s), 6.58 (1 H, dd, J=2.4, 8.7 Hz), 6.65 (1 H, d, J=2.4 Hz), 7.11 (2 H, d, J=8.7 Hz), 7.38 (1 H, d, J=8.7 Hz), 7.42 – 7.47 (3 H, m), 7.87 (2 H, d, J=8.7 Hz), 7.99 – 8.04 (2 H, m).

According to the analysis of related databases, 609-12-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1911738; (2008); A1;,
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Electric Literature of 53518-15-3, 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. 53518-15-3, name is 7-Amino-4-(trifluoromethyl)-2H-chromen-2-one belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

7-Amino-4-trifluoromethylcoumarin 3.71 g (16.2 mmol) was dissolved in dichloromethane (20 mL). After slow addition of the distilled pyridine (20 mL) and p-toluenesulfonyl chloride (6.80 g, 35.7 mmol), the mixture was then stirred for 4 h at room temperature. Then ethyl acetate 150 mL was added, followed by wash of citric acid solution for three times and brine once. The resulting solution was dried with sodium sulfate and evaporated, washed with a small portion of cooled dichloromethane and dried in vacuo to give the compound 2 as white solid. Yield: 5.64 g (91%). Mp 193-194 C. 1H NMR (CDCl3, 400 MHz): delta 7.81 (d, J=8.0 Hz, 2H), 7.57 (d, J=8.8 Hz, 1H), 7.30 (d, J=8.0 Hz, 2H), 7.21 (d, J=2.4 Hz, 1H), 7.08 (dd, J1=2.0 Hz, J2=2.0 Hz, 1H), 6.67 (s, 1H), 2.40 (s, 3H). EI-MS: m/z, calcd 383.34, found 383.02.

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, 7-Amino-4-(trifluoromethyl)-2H-chromen-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Li, Jun; Zhang, Chun-Fang; Ming, Ze-Zhong; Hao, Ge-Fei; Yang, Wen-Chao; Yang, Guang-Fu; Tetrahedron; vol. 69; 23; (2013); p. 4743 – 4748;,
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Electric Literature of 1245643-11-1, 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. 1245643-11-1, name is Methyl 3,4-diamino-5-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of a mixture of intermediates 3a and 3b (75/25 evaluated by LC/MS) (195g, 554 mmol) in DMSO (2000 mL) was added vinylbutylether (166 g, 1661. mmol) and tri- ethyl amine (400 mL, 2768 mmol, 0.7g/mL) under N2atmosphere. Pd(OAc)2(12.4g, 55mmol) and DPPP (45.6g, 11 lmmol) were added. The mixture was purged again with N2and heated to 100 C overnight. After cooling down to room temperature, HCl (3M, 1845mL, 5536 mmol) was added portionwise under ice batch and the mixture was stirred for 1 hour. The pH of the mixture was adjusted to 8 with NaHC03. The mixture was filtered. The cake was washed with ethyl acetate (1000 mL), then dissolved in CH2C12(1500 mL*2) and filtered. The filtrate was washed with brine (500 mL), evaporated to give a crude yellow solid (200 g) mainly containing intermediate 8a. This residue was purified by silica gel chromatography (eluent: ethyl acetate= 100%). The desired fractions were collected and the solvent was concentrated to dryness under vacuum to give 100 g (57%>) of intermediate 8a as yellow solid.Alternatively, the previous reaction was also carried out using EtOH as solvent at a temperature of 70C.

The synthetic route of Methyl 3,4-diamino-5-bromobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ANGIBAUD, Patrick, Rene; QUEROLLE, Olivier, Alexis, Georges; BERTHELOT, Didier, Jean-Claude; MEYER, Christophe; WILLOT, Matthieu, Philippe, Victor; MEERPOEL, Lieven; JOUSSEAUME, Thierry, Francois, Alain, Jean; (114 pag.)WO2018/178280; (2018); A1;,
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Electric Literature of 23877-12-5, A common heterocyclic compound, 23877-12-5, name is tert-Butyl 2-bromo-2-methylpropanoate, molecular formula is C8H15BrO2, 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 III-2 tert-Butyl 2-(4-formylphenoxy)-2-methylpropanoate 24.42 g (200 mmol) of 4-hydroxybenzaldehyde are dissolved in 250 ml of N,N-dimethylformamide and treated with 27.64 g (200 mmol) of potassium carbonate. At 100 C., 53.55 g (240 mmol) of tert-butyl alpha-bromoisobutyrate are added dropwise. The mixture is stirred for another hour, a further 200 mmol of potassium carbonate and 240 mmol of tert-butyl alpha-bromoisobutyrate are added and, after 4 hours at 100 C., 1 l of water is added. Following extraction with diethyl ether, washing with 1 N aqeuous sodium hydroxide solution and saturated sodium chloride solution and drying over magnesium sulphate, the solvent is distilled off and the residue is purified by flash chromatography on silica gel (cyclohexane?cyclohexane/ethyl acetate 20:1?10:1?5:1) and dried under reduced pressure. The target compound is obtained in the form of colourless crystals in a yield of 42%. 1H-NMR (200 MHz, CDCl3): delta=1.40 (s, 9H), 1.62 (s, 6H), 6.91 (d, 2H), 7.79 (d, 2H), 9.88 (s, 1H). MS (ESI): 265 [M+H]+.

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; Urbahns, Klaus; Woltering, Michael; Nikolic, Susanne; Pernerstorfer, Josef; Hinzen, Berthold; Dittrich-Wengenroth, Elke; Bischoff, Hilmar; Hirth-Dietrich, Claudia; Lustig, Klemens; US2003/32671; (2003); A1;,
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Adding a certain compound to certain chemical reactions, such as: 99974-66-0, name is Diethyl 3-hydroxycyclobutane-1,1-dicarboxylate, 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 99974-66-0, Quality Control of Diethyl 3-hydroxycyclobutane-1,1-dicarboxylate

Compound BB3-C (0.8 g, 0.0037 mol) was dissolved in dry DCM (16 mL) and cooled to 0 C. DAST (1.8 g, 0.011 mol) was added drop-wise to the cold solution. The reaction mixture was warmed to room temperature stirred for 12 h. The reaction mixture was quenched with cold saturated aHC03 solution. The crude product was extracted with DCM (100 mL). The organic layer was washed with 10 % NaHCOi solution, water followed by brine and dried over anhydrous Na2SO/t. Solvent was concentrated in vacuum and the crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 1-2 % EtOAc in pet ether) which afforded the title compound as a pale yellow liquid (460 mg, yield 57 %). TLC system: 10% EtOAc in pet ether, Rf= 0.4.

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 3-hydroxycyclobutane-1,1-dicarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MEDIVIR UK LIMITED; AYESA, Susana; CARLQUIST, Peter; ERSMARK, Karolina; GRABOWSKA, Urszula; HEWITT, Ellen; JOeNSSON, Daniel; KAHNBERG, Pia; KLASSON, Bjoern; LIND, Peter; ODEN, Lourdes; PARKES, Kevin; WIKTELIUS, Daniel; WO2011/70541; (2011); 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. 1014645-87-4, name is Methyl 4-(1-aminocyclopropyl)benzoate hydrochloride, A new synthetic method of this compound is introduced below., Quality Control of Methyl 4-(1-aminocyclopropyl)benzoate hydrochloride

Description 142: methyl 4-(1-(5-chloro-2-(2-phenylpyrrolidin-1- yl)nicotinamido)cyclopropyl)benzoate (D142)A solution of 5-chloro-2-(2-phenylpyrrolidin-1 -yl)nicotinic acid (D98) (150 mg, 0.5 mmol), methyl 4-(1 -aminocyclopropyl)benzoate hydrochloride (D7) (1 14 mg, 0.5 mmol) and N,N-Diisopropylethylamine (194 mg, 1 .5 mmol) in dimethylformamide (10ml) was stirred 1 h at room temperature, then benzotriazol-1 -yl- oxytripyrrolidinophosphonium hexafluorophosphate (PyBOP) (312 mg, 0.6 mmol) was added. The mixture was stirred at room temperature overnight, then poured into ice-water (20ml) and extracted with ethyl acetate (2x20ml). The organic solution was washed with brine (40ml), dried over Na2S04 and concentrated to obtain a residue which was purified by flash chromatography on silica gel eluting with a mixture petroleum ether/ethyl acetate (4:1 ). Collected fractions after solvent evaporation afforded the title compound (D142) (189 mg) as a yellow solid.1 H NMR (400MHz ,CHLOROFORM-d) delta (ppm): 8.10 (1 H, d, J = 2.4 Hz) 8.03 – 8.00 (2H, m) 7.74 (1 H, d, J = 2.4 Hz) 7.67 (1 H, s) 7.41 (2H, d, J = 8.0 Hz) 7.28 – 7.18 (5H, m) 5.36 – 5.32 (1 H, m) 3.91 (3H, s) 3.69 – 3.63 (1 H, m) 3.16 – 3.1 1 (1 H, m) 2.43 – 2.37 (1 H, m) 1 .97 – 1 .87 (3H, m) 1 .49 – 1 .39 (4H, m)

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; ROTTAPHARM S.P.A.; BORRIELLO, Manuela; ROVATI, Lucio; STASI, Luigi Piero; BUZZI, Benedetta; COLACE, Fabrizio; WO2012/76063; (2012); A1;,
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Application of 150529-73-0,Some common heterocyclic compound, 150529-73-0, name is Methyl 2-(3-bromophenyl)acetate, molecular formula is C9H9BrO2, 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 dry 100 mL three-necked flask was added methyl 3-bromophenylacetate (4.58 g, 20 mmol, 1.0 eq) under N2.Add anhydrous tetrahydrofuran (30 mL),A 2.0 M solution of lithium diisopropylamide in THF / heptane / ethylbenzene (10.5 mL, 21 mmol, 1.05 eq) was slowly added dropwise at -78 C.After the completion of the dropwise addition, the mixture was stirred for 30 minutes, and then methyl iodide (2.84 g, 20 mmol,1.0eq). Stirring was continued at room temperature for a further 3 hours.60 mL of water was added to the reaction flask, followed by extraction with 50 mL of dichloromethane, and the mixture was separated.The aqueous phase was extracted twice more with 30 mL of dichloromethane. Combine the organic phase,Wash twice with saturated saline solution,Drying with anhydrous sodium sulfate, concentration, and the residue was separated by column chromatography.Methyl 2-(3-bromophenyl)propanoate 3.95 g was obtained in a yield of 82.3%.

The synthetic route of 150529-73-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shenzhen Xianggen Biological Technology Co., Ltd.; Peng Jinan; Li Fanglin; Zhang Qishan; Luo Yuting; Xiao Qicai; Gao Liqian; (10 pag.)CN108794319; (2018); A;,
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Synthetic Route of 52787-14-1, A common heterocyclic compound, 52787-14-1, name is Methyl 4-(2-methoxy-2-oxoethyl)benzoate, molecular formula is C11H12O4, 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.

2- (4- (methoxycarbonyl) phenyl) acetic acid (58,24.04 dirty 1) to the reaction flask, 31111 water, 31111 5ml tetrahydrofuran and a mixed solvent of ethanol raw materials were dissolved. Was then added Eta0Eta-Eta20 (1.068,25.24pipiomicron1) alpha25 C was stirred for 10 hours the reaction is substantially complete. The solution was spin-off in tetrahydrofuran and ethanol, followed by addition of 26ml of dilute hydrochloric acid (lmmol / L), and a white precipitate formed, suction, infrared drying to give a white solid 4.4g, 94.4% yield

The synthetic route of 52787-14-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; China Pharmaceutical University; Xiang, Hua; Xu, Pei; Wang, Wenbin; Qian, Zhouyang; Chen, Mingqi; You, Qidong; (15 pag.)CN105541777; (2016); A;,
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Synthetic Route of 135484-83-2, 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. 135484-83-2, name is Methyl 2-amino-4-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[00404] Step A: Methyl 2-amino-4-bromobenzoate was prepared from the corresponding acid by Fischer esterification. A mixture of methyl 2-amino-4- bromobenzoate (1.1 g, 4.8 mmol) and ethyl carbonocyanidate (0.95 g, 9.66 mmol) in HOAc (4 mL) was treated with a sl2 N HCl (0.4 mL) and the resulting mixture was stirred at 700C for 3 h. After cooling to rt, water was added followed by addition of aq sodium hydrogen carbonate to pH ~5. The precipitated solid was filtered and washed thoroughly with water and diethyl ether to afford ethyl 7-bromo-4-oxo-3,4- dihydroquinazoline-2-carboxylate (825 mg, 58%). 1H NMR (300 MHz, DMSO-d6) delta 12.82 (s, IH), 8.06-8.09 (m, 2H), 7.81 (d, J= 8.4 Hz, IH), 4.38 (q, J= 7.0 Hz, 2H), 1.35 (t, J= 7.0 Hz, 3H); LC-MS (ESI) m/z 296 (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, Methyl 2-amino-4-bromobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMBIT BIOSCIENCES CORPORATION; LIU, Gang; CHAO, Qi; HADD, Michael, J.; HOLLADAY, Mark, W.; ABRAHAM, Sunny; SETTI, Eduardo; WO2010/99379; (2010); A1;,
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