Tag: M.W=200-300

These common heterocyclic compound, 59247-47-1, name is tert-Butyl 4-bromobenzoate, 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. Recommanded Product: 59247-47-1

A 3-neck flask was charged with NaOtBu (2.85 g, 28.6 mmol) and dry THF (50 mL) under nitrogen. Tris(dibenzylideneacetone)dipalladium(0) (0.26 g, 0.28 mmol) and (S)-ToI- Binap (0.47 g, 0.69 mmol) were then added under nitrogen. After stirring for 15 min, l-(4- chlorophenyl)pentan-l-one (4.21 g, 21.0 mmol) was added, followed by tert-butyl 4- bromobenzoate (5.0 g, 19.1 mmol) under nitrogen. The mixture was heated at 600C for 8 hours. The mixture was diluted with heptane (100 mL) and poured into a solution of saturated NaHCO3 (aq) (60 mL) and ice (40 g). The resulting layers were separated, and the aqueous phase was back-extracted with methyl tert-butyl ether (50 mL). The combined organics were washed with saturated NaHCO3 (aq) then 10percent NaCl (aq). The organic solution was filtered through a bed of silica 60 (84 g, wetted with 1 :1 methyl tert-butyl ether/heptane), and washed with 1:1 methyl tert-butyl ether/heptane (600 mL). The combined filtrate was concentrated to afford an orange oil that was used directly for the next step: 1H NMR (500 MHz, CDCl3): delta 7.91 (d, J = 8.1 Hz, 2 H); 7.86 (d, J = 8.4 Hz, 2 H); 7.35 (d, J = 8.4 Hz, 2 H); 7.32 (d, J – 8.2 Hz, 2 H); 4.53 (t, J = 7.2 Hz, 1 H); 2.19-2.09 (m, 1 H); 1.85-1.76 (m, 1 H); 1.56 (s, 9 H); 1.35-1.18 (m, 2 H); 0.91 (t, J = 7.3 Hz, 3 H); LCl : 1.35 min. (M-tBu+H)+ 317.

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

Reference:
Patent; MERCK SHARP &; DOHME CORP.; LIN, Songnian; ZHANG, Fengqi; PARMEE, Emma, R.; DEWNANI, Sunita, V.; WO2010/88061; (2010); A1;,
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Synthetic Route of 46064-79-3, 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. 46064-79-3 name is Methyl 3-amino-4-bromobenzoate, 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.

A mixture of ethyl 1-benzyl-3-oxopiperidine-4-carboxylate (16.1 g, 70 mmol), methyl 3-amino-4-bromobenzoate (21.9 g, 84 mmol), polyphosphoric acid (120 g) and dioxane (120 mL) was heated at 110 C for 4 hours. After cooling to room temperature, the mixture was poured into ice water, filtered and the filtrate was extracted with EtOAc (500 mL x3). The combined organic layers were dried, and concentrated to give crude residue, which was chromatographed on silica gel using gradient eluant of 20% to 50% ethyl acetate in petroleum ether to give the crude product. Then the crude product was dissolved in MeOH (1 L), TMSCl (150 mL) was added, and the mixture was stirred at reflux for 12 h. After cooling to room temperature, the solvent was evaporated and the residue was recrystallized from MeOH to afford methyl 2-benzyl-9-bromo-5-oxo-1,2,3,4,5,10-hexahydrobenzo[b][1,7]naphthyridine-6-carboxylate (7.6 g).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-amino-4-bromobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; BEIGENE, LTD.; ZHOU, Changyou; REN, Bo; WANG, Hexiang; WO2013/97226; (2013); A1;,
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Reference of 40876-98-0, A common heterocyclic compound, 40876-98-0, name is Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate, molecular formula is C8H11NaO5, 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.

Step 1: 6-hydroxypyrimidine-4-carboxylic acid 63.5 g (0.29 mol) sodium diethyloxalacetate and 30.2 g (0.29 mol) formamidine acetate were added to 24.1 g (0.6 mol) NaOH in 3.6 L water. The mixture was stirred overnight at RT. Then activated charcoal was added and the mixture was refluxed for 1 h. It was filtered off hot and after cooling acidified with aqueous hydrochloric acid. The solution was evaporated to dryness by rotary evaporation. The residue contained the desired product and was used in the next step without any further purification. Yield: 83.0 g

The synthetic route of 40876-98-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/195954; (2011); A1;,
Ester – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 57381-62-1, name is Methyl 2-bromo-4-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 57381-62-1, name: Methyl 2-bromo-4-chlorobenzoate

In a 500 ml round-bottomed flask, 30 g (68.9 mmol) of the compound of formula C-1,17 g (68.2 mmol) of methyl 2-bromo-4-chlorobenzoate,1.6 g (1.38 mmol) of tetrakistriphenylphosphine palladium was added to 150 ml of tetrahydrofuran, mixed with 80 ml of an aqueous solution of 28.6 g (207 mmol) of potassium carbonate and refluxed for 24 hours. The impurities were removed using chloroform and water, and then anhydrous magnesium sulfate was added to remove moisture. The solution was filtered and then recrystallized using chloroform and ethanol to obtain 21.2 g (yield 65percent) of the formula C-2.

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

Reference:
Patent; LG Chemical Co.,Ltd; Kim, Su Yeon; Lee, Ho Yong; Jo, Sung Mi; (43 pag.)KR2016/2354; (2016); A;,
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Synthetic Route of 457097-93-7, These common heterocyclic compound, 457097-93-7, name is Methyl 4-amino-3-(trifluoromethoxy)benzoate, 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.

(b) 4-Amino-3-chloro-5-trifluoromethoxy-benzoic acidmethyl ester The product of the previous step (200.0 mg, 0.74 mmol) was dissolved in a mixture of ACN (9.44 mL) and DMA (0.944 mL) at RT. To this stirred solution was added N-chlorosuccinimide (108.2 mg, 0.81 mmol). The resulting mixture was heated at 60 C. for 1 h, cooled to RT and partitioned between EtOAc (20 mL) and saturated sodium bicarbonate (4 mL). The organic layer was washed with saturated sodium bicarbonate (4 mL) and brine (4 mL), dried over sodium sulfate, filtered, and concentrated to give a yellowish oil, which was purified by silica gel chromatography (12 g silica gel, 0-40% EtOAc/hexanes) to give the title intermediate as a white solid (173.8 mg, 88% yield). Structure confirmed by NMR.

The synthetic route of 457097-93-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LONG, Daniel D.; MCKINNELL, Robert Murray; JIANG, Lan; LOO, Mandy; LEPACK, Kassandra; VAN ORDEN, Lori Jean; OGAWA, Gavin; HUANG, Xiaojun; ZHANG, Weijiang; US2013/115194; (2013); A1;,
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Reference of 39503-58-7, 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. 39503-58-7, name is Methyl 5-bromo-2-methoxy-4-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows.

The bromo derivative from above (44.5 g, 0.17 mol) was added in small portions to conc. H2SO4 (170 mL) and the mixture was stirred in an ice-salt bath until all SOLIDS DISSOLVED. CONC. HN03 (17 mL) was then added dropwise over 20 min and stirring continued for an additional hour in the ice bath. The reaction mixture was then slowly added to ice-water (2 L) and the precipitated yellow solid was collected by filtration. The solid was washed with water, NAHC03 solution and water again. After drying, the desired nitro derivative was obtained as an orange solid (36.8 g).

The chemical industry reduces the impact on the environment during synthesis Methyl 5-bromo-2-methoxy-4-methylbenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO KG; WO2004/65367; (2004); A1;,
Ester – Wikipedia,
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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. 107045-28-3, name is tert-Butyl 4-(aminomethyl)benzoate, A new synthetic method of this compound is introduced below., Quality Control of tert-Butyl 4-(aminomethyl)benzoate

To a stirred solution of 5-chloro-2-hydroxybenzoic acid (0.57 g, 3.3 mmol) and tert-butyl 4-(aminomethyl)benzoate (0.72 g, 3.5 mmol) in dichloromethane (5 mL) were successively added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCl) (0.95 g, 5.0 mmol), 1-hydroxybenzotriazole hydrate (HOBT) (0.76 g, 5.0 mmol), and triethylamine (0.46 mL, 3.3 mmol). After being stirred overnight, the reaction mixture was poured into sodium bicarbonate aqueous solution (50 mL). The organic layer was separated, and the aqueous layer was extracted with dichloromethane (20 mL*2). The combined organic layers were washed with brine (50 mL), dried (magnesium sulfate), and evaporated. The residue was purified by flush column chromatography on silica gel eluding with hexane/ethyl acetate (10/1) to afford 0.57 g (48%) of the title compound as white solids: 1H-NMR (CDCl3) delta 12.12 (1H, s), 7.99 (2H, d, J=7.9 Hz), 7.47-7.30 (4H, m), 6.97 (1H, d, J=8.4 Hz), 6.67-6.52 (1H, m), 4.68 (2H, d, J=5.7 Hz), 1.59 (9H, s).

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; Pfizer Inc; US2005/250818; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 1245643-11-1, name is Methyl 3,4-diamino-5-bromobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H9BrN2O2

In a sealed glassware, a mixture of intermediate 3a and intermediate 3b (75/25) (10 g; 28.39 mmol), N-boc-2,3-dihydro-lH-pyrrole (6.86 mL; 39.75 mmol) and K2CO3 (11.8 g; 85.18 mmol) in 1,4-dioxane (250 mL) was bubbled with N2. Then, PPh3(1.49 g; 5.68 mmol) and Pd(OAc)2(640 mg; 2.84 mmol) were added. The reaction mixture was heated to 100C for 5h. The reaction mixture was cooled down to rt, poured onto water and extracted with EtOAc. The organic layer was decanted, washed with brine, dried over MgS04, filtered and evaporated to dryness. The residue (21 g) was purified by chromatography over silica gel (irregular SiOH; 20-45 muiotaeta; 450 g; mobile phase: 62%> heptane, 3% MeOH (+10% NH4OH), 35% EtOAc). The pure fractions were collected and evaporated to dryness yielding 2.3 g (17%>, impure) of intermediate 16a and 8.2 g (59%) of intermediate 16a.

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 1245643-11-1.

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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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. 106896-49-5, name is Methyl 4-amino-3-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: Methyl 4-amino-3-bromobenzoate

General procedure: PCl5 (0.23 g, 1.1 mmol) was added to an ice-cold solution of compound 6 (0.30 g, 1 mmol) in ether (15 mL). The reaction mixture was stirred at room temperature for 2 h and then was concentrated under reduced pressure. The crude product was dissolved in THF (15 mL). The arylamine (1 mmol) and triethylamine (1.2 mmol) was added to the solution successively. The reaction mixture was stirred at room temperature for 2 h and then was then evaporated under reduced pressure. The residue was chromatographed on silica gel using ethyl acetate:petroleum ether (1:4). Pure fractions were collected and concentrated, giving the desired compound (7a-7o).

The synthetic route of 106896-49-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhan, Peng; Chen, Xuwang; Li, Xiao; Li, Dongyue; Tian, Ye; Chen, Wenwen; Pannecouque, Christophe; De Clercq, Erik; Liu, Xinyong; European Journal of Medicinal Chemistry; vol. 46; 10; (2011); p. 5039 – 5045;,
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Some common heterocyclic compound, 57053-02-8, name is Dimethyl 2-aminoisophthalate, molecular formula is C10H11NO4, 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. HPLC of Formula: C10H11NO4

2,6-Di(4-hydroxyheptan-4-yl)aniline Xlb (R2 = B). A suspension of fresh magnesium (20.9 g, 0.86 mol, 8.6 eq) in anhydrous THF (300 mL) was treated with the slow addition of a premade solution of n-propylbromide (69.5 mL, 0.77 mol, 7.7 eq) in anhydrous THF (300 mL) over 20 mm in maintaining the temperature below 40 DC. After 1.5 h at room temperature, the suspension was cooled down to 0 DC, causing theformation of a precipitate, and a premade solution of diester X (where R1 is methyl) (20.0 g, 0.10 mol, 1.0 eq) in dry THF (300 mL) was cannulated at 0 DC. The reaction was allowed to warm up to room temperature and was stirred for 2 h. The reaction was then cooled down to 0 DC and carefully quenched with sat. NH4CI solution (300 mL). The mixture was diluted in Et20 (400 mL) and washed with sat. NH4CI solution (2 x 200mL). The organic layer was then dried over anhydrous magnesium sulphate and concentrated under vacuum. The resulting brown crude solid (30.9 g) (Pure by 1H NMR) was then further purified by successive recrystallisation from pentane to give the pure diol XIb (26.6 g, 86%) as a white crystalline solid.1H NMR (400 MHz, CDCI3) 60.90 (12H, app t, J = 7.3 Hz, 4 x CH3), 1.08-1.23 (4H, m,4 x CH), 1.26-1.41 (4H, m, 4 x CH), 1.78-1.88 (4H, td, J = 12.5, 4.5 Hz, 4 x CH), 1.95-2.05 (4H, td, J =12.5, 4.5 Hz, 4 x CH), 4.24 (3H, vbs, NH2 + 2 x OH), 6.54 (1H, t, J =7.7 Hz, H), 6.89 (2H, d, J = 7.7 Hz, H?).13C {H} NMR (100 MHz, COd3) 6 14.5(4 x CH3), 17.2(4 x CH2), 41.2 (4 x CH2), 79.4(2 x C,-OH), 115.1 (CH/1), 126.5(2 x CH(nAr), 128.7(2 x CHOAr), 146.7 (CivNH2). HRMS (NSI+): found m/z [M + H]+ 322.2745, calcd for C20H36O2N 322.2741.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 57053-02-8, its application will become more common.

Reference:
Patent; UNIVERSITY COURT OF THE UNIVERSITY OF ST ANDREWS; NOLAN, Steven P; MEIRIES, Sebastien; WO2014/108671; (2014); A1;,
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