Author: Jessica.F

Reference of 18595-18-1, The chemical industry reduces the impact on the environment during synthesis 18595-18-1, name is Methyl 3-amino-4-methylbenzoate, I believe this compound will play a more active role in future production and life.

Step 1: Preparation of methyl 1H-indazole-6-carboxylate (A-2) [0301] Methyl 3-amino-4-methylbenzoate (A-1) (5.0 g, 30.2 mmol) was dissolved in AcOH (140 mL). Sodium nitrite (2.1 g, 30.2 mmol) in water (3.5 mL) was added drop-wise to the solution while stirring at 0 C. The ice bath was removed and the mixture was stirred overnight. Solvents were evaporated, and the mixture was diluted with water (80 mL) and extracted with EtOAc (3×30 mL). The combined organics were washed with water and brine (2×200 mL), dried and evaporated to afford 2 (4.4 g), yield 83%. LCMS (ESI): calc’d for C9H8N2O2, [M+H]+: 177. found: 177.

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

Reference:
Patent; Barr, Kenneth J.; Maclean, John K.; Zhang, Hongjun; Beresis, Richard T.; Zhang, Dongshan; Andresen, Brian M.; Anthony, Neville J.; Lapointe, Blair T.; Sciammetta, Nunzio; US2015/191434; (2015); A1;,
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These common heterocyclic compound, 32122-09-1, name is Ethyl 2-(benzyloxy)acetate, 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. Application In Synthesis of Ethyl 2-(benzyloxy)acetate

Preparation of intermediate G-1. TiCI4, Bu3N,1 -methylimidazoleA-1 G-1To a stirred solution of A-1 (60 g, 309 mmol, 1 eq) and 1 -methylimidazole (30.4 g, 370 mmol, 1 .2 eq) in CH2CI2 (1 L) was added acetyl chloride (24.3 g, 309 mmol, 1 eq) at -45 C under N2. After stirring for 20 min, TiCI4 (210 g, 1 .08 mol, 3.5 eq) and tributylamine (230 g, 1 .24 mol, 4 eq) were added to the mixture at -45C under N2, and continues to stir for 50 minutes at -45C under N2. After completion, water and ethyl acetate were added. The organic layer was separated and the aqueous layer was extracted with ethyl acetate twice. The organic layer was washed with brine and dried over sodium sulfate. The solids were removed by filtration and the solvents of the filtrate were removed under reduced pressure. The crude was purified via silica column chromatography using a heptane to ethyl acetate gradient to afford a pale yellow oil, G-1. 1H NMR (400 MHz, CHLOROFORM-cf) delta ppm 1 .30 (t, J=7.2 Hz, 3 H), 2.28 (s, 3 H), 4.27 (q, J=7.2 Hz, 2 H), 4.41 (s, 1 H), 4.58 (d, J=1 1 .8 Hz, 1 H), 4.75 (d, J=1 1 .8 Hz, 1 H), 7.32 – 7.43 (m, 5 H)

The synthetic route of Ethyl 2-(benzyloxy)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN R&D IRELAND; MC GOWAN, David; RABOISSON, Pierre Jean-Marie Bernard; EMBRECHTS, Werner; JONCKERS, Tim, Hugo, Maria; LAST, Stefaan, Julien; PIETERS, Serge, Maria, Aloysius; VLACH, Jaromir; WO2012/136834; (2012); A1;,
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10601-80-6, name is Ethyl 3,3-diethoxypropionate, 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. HPLC of Formula: C9H18O4

4-Chloro-2-nitrobenzaldehyde (3.71 g, 0.02 mol) was dissolved in ethanol (40 ml).Further adding stannous chloride (18.04g, 0.08mol) and ethyl 3,3-diethoxypropionate (9.5g, 0.05mol), and reacting at 90 C for 4 hours, the reaction of the raw materials of the plate is completed; After the solvent was added, ethyl acetate was dissolved, and neutralized to a weak basic with saturated sodium carbonate; filtered, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate, and then the organic layer was combined, and then evaporated to dryness. Ethyl acetate = 10:1, then petroleum ether: ethyl acetate = 5:1) After washing, ethyl 7-chloro-3-quinolinecarboxylate (3.478 g, 74%).

The synthetic route of 10601-80-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Suzhou Kangrun Pharmaceutical Co., Ltd.; Jin Haowen; Xu Weiliang; Xu Weizheng; (8 pag.)CN108484497; (2018); A;,
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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. 56741-34-5, name is Methyl 5-amino-2-fluorobenzoate, A new synthetic method of this compound is introduced below., name: Methyl 5-amino-2-fluorobenzoate

A solution of 5-amino-2-fluorobenzoic acid methyl ester (340 mg, 2 mmol), 6-mercaptonicotinic acid (310 mg,2 mmol), and EEDQ (500 mg, 2 mmol) in anhydrous DMF (4 mL) was stirred overnight under N2 at room temperature,2-Bromomethylphenyl boronic acid (428 mg, 2 mmol) was added to the reaction mixture for another 16 hours at roomtemperature. The solvent was then removed by rotary evaporation, and the residue dissolved in EtOAc (25 mL), Theorganic layer was washed with H2O, 10% Na2CO3, H2O, 1 N HCl, H2O, brine, and dried over Na2SO4. The organic layerwas filtered and evaporated to yield 597 mg (68%) of the methyl ester derivative as a light yellow solid. The methyl esterintermediate (200 mg, 0.45 mmol) was dissolved in MeOH (6 mL) and 1 N NaOH (1.35 mL) was added to the reactionmixture. The reaction was stirred for 16 hours at room temperature. The MeOH was removed by rotary evaporation,and the resulting solution acidified with IN BCl. The resulting solid was washed and dried to yield 87 mg (45%) as anoff white solid. ESI-MS m/z = 426.93 [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; Syntrix Biosystems, Inc.; Maeda, Dean Y.; Zebala, John A.; EP2942346; (2015); A1;,
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23877-12-5, Adding some certain compound to certain chemical reactions, such as: 23877-12-5, name is tert-Butyl 2-bromo-2-methylpropanoate, 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 23877-12-5.

2-Methyl-2-{4-[3-(4-trifluoromethyl-phenyl)-[1,2,4]thiadiazol-5-ylmethylsulfanyl]-phenoxy}-propionic acid tert-butyl ester To a three-necked flask containing NaH (36 mg, 0.90 mmol; 60% in mineral oil) was added a solution of B1 (220 mg, 0.598 mmol) in THF. To the mixture at 40 C. was added tert-butyl 2-bromoisobutyrate (287 mg, 1.29 mmol). After heating at 70 C. for 2 h, more tert-butyl 2-bromoisobutyrate (215 mg, 0.970 mmol) was added and the heating was continued overnight. The mixture was quenched with water (0.1 mL), concentrated, and chromatographed (EtOAc/hexane) to give 81 mg (27%) of B2; 1H NMR (300 MHz, CDCl3) delta 8.35 (d, J=8.2 Hz, 2 H), 7.71 (d, J=8.2 Hz, 2 H), 7.34 (d, J=8.8 Hz, 2 H), 6.78 (d, J=8.7 Hz, 2 H), 4.42 (s, 2 H), 1.55 (s, 6 H), 1.38 (s, 9 H); MS (ES) m/z: 511 (M+H+).

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 23877-12-5.

Reference:
Patent; Kuo, Gee-Hong; Shen, Lan; Wang, Aihua; Zhang, Yan; US2005/96362; (2005); 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. 154825-97-5, name is Methyl 2-(4-bromophenyl)-2,2-dimethylacetate, A new synthetic method of this compound is introduced below., HPLC of Formula: C11H13BrO2

Preparation of Intermediate 1 -bromo-4-(1 -methoxy-2-methylpropan-2-yl)benzene (1AA- 11; Methyl 2-(4-bromophenyl)-2-methylpropanoate (23.5g, 86.6mmol) in tetrahydrofuran (175ml_) was cooled to -78C. Lithium aluminum hydride (100 ml. of 1.0 M solution) added slowly over 45 minutes and stirred for 3 hours at cold temperature. Reaction solution was slowly diluted with ethyl acetate and stirred for 10 minutes. 1 M hydrochloric acid was slowly added drop wise to reaction mixture. Diethyl ether (20OmL) added and layers separated. Organic washed with 1 M hydrochloric acid, brine, dried over sodium sulfate, filtered and concentrated to give 2-(4-bromophenyl)-2- methylpropan-1-ol (20m, 100%) as a white solid.

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.; ASPNES, Gary, Erik; DOW, Robert, Lee; MUNCHHOF, Michael, John; WO2010/86820; (2010); A1;,
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Related Products of 685892-23-3, 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. 685892-23-3, name is Methyl 2-bromo-6-chlorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 4; 4′-{(R)-1-[(3-Amino-oxetane-3-carbonyl)-amino]-ethyl}-3-chloro-3′-fluoro-biphenyl-2-carboxylic acid methyl ester Step A: 4′-((R)-1-tert-Butoxycarbonylamino-ethyl)-3-chloro-3′-fluoro-biphenyl-2-carboxylic acid methyl ester A mixture of {(R)-1-[2-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethyl}-carbamic acid tert-butyl ester (600 mg, 1.64 mmol, intermediate 13), methyl 2-bromo-6-chlorobenzoate (430 mg, 1.72 mmol) [CAS 685892-23-3; commercially available], tri-o-tolyl-phosphane (100 mg, 329 mumol), potassium carbonate (568 mg, 4.11 mmol) and palladium(II) acetate (18.4 mg, 82.1 mumol) in THF (20.0 ml) and water (1.18 ml) was stirred at room temperature over night. The reaction mixture was diluted with water and extracted three times with EtOAc. The combined extracts were washed with water and brine, dried with Na2SO4 and concentrated in vacuo. The remaining residue was purified by chromatography (silica gel; DCM/EtOAc 100:0-90:10) and the title compound was obtained as colorless oil (385 mg, 58%). MS: 466.1 [M-H+OAc]-.

The chemical industry reduces the impact on the environment during synthesis Methyl 2-bromo-6-chlorobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Aebi, Johannes; Binggeli, Alfred; Hertel, Cornelia; Konkar, Anish Ashok; Kuehne, Holger; Kuhn, Bernd; Maerki, Hans P.; Wang, Haiyan; US2012/165338; (2012); A1;,
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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. 89-91-8, name is Methyl 2,2-dimethoxyacetate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Methyl 2,2-dimethoxyacetate

A diethyl ether solution of ethylmagnesium bromide (concentration=2 1.85 mass %, 277 g) was added to a reaction flask and was cooled to around 0 C. by stirring on an ice-cooling bath. A Grignard reaction was carried out by the dropwise addition to this solution over one hour of methyl dimethoxyacetate (25 g). This was followed by return to room temperature and reaction for 12 hours. The reaction solution was ice-cooled; 200 g of a saturated aqueous ammonium chloride solution was added dropwise; and the pH was subsequently adjusted to around neutrality by the dropwise addition of 10 mE of a 36% hydrochloric acid solution. The solution was then transferred to a separatory funnel; the organics were extracted with 50 g of hexane and separated; and drying was carried out over an appropriate amount of magnesium sulfate. This hexane suspension was filtered followed by removal of the solvent on an oil bath at around 65 C. Distillation was performed under reduced pressure on an oil bath at around 100 C. to obtain 22.4 g of a transparent and colorless 3-dimethoxym- ethyl-3-pentanol (GC purity=96.3%). 10 g of pure water and 1 g of 36% hydrochloric acid were added under ice cooling to 7 g of the 3-dimethoxymethyl-3-pentanol and stirring was carried out overnight. After this, 9.5 g of a 33% aqueous ethylamine solution was added dropwise under ice cooling and a reaction was run for 10 hours. The pH of the reaction solution at this time was 10 to 11. When stirring was stopped, separation occurred into an aqueous layer and a small amount of an organic layer, and the organic layer was determined to be alcohol compound No. 140 according to the NMR results. 2.7 g of the target was obtained for a yield of 33%.

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 89-91-8.

Reference:
Patent; ADEKA CORPORATION; SAKURAI, Atsushi; HATASE, Masako; YOSHINO, Tomoharu; ENZU, Masaki; (40 pag.)US2017/129912; (2017); A1;,
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Application of 1130165-74-0, 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 1130165-74-0 as follows.

(1) A mixture of ethyl 4-bromo-3-fluorobenzoate (500 mg), tris(dibenzylideneacetone)dipalladium (0) (94 mg), (R)-(+)-(1,1′-binaphthalene-2,2′-diyl)bis(diphenylphosphine) (189 mg), cesium carbonate (1.98 g), (R)-pyrrolidin-3-ol (353 mg), and toluene (5 mL) was stirred for 1 hour under heating and refluxing. The reaction mixture was cooled to room temperature and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent; 70%-30% n-hexane/ethyl acetate] to obtain ethyl (R)-3-fluoro-4-(3-hydroxypyrrolidin-1-yl)benzoate (390 mg) as a brown oily substance. MS (ESI nm/z): 254 (M+H) RT (min): 1.41

According to the analysis of related databases, 1130165-74-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FUJIFILM Corporation; Ookubo, Megumi; Sekine, Shinichiro; Mashiko, Tomoyuki; Kawai, Hyoei; Fukunaga, Hirofumi; US2020/17459; (2020); A1;,
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23676-08-6, name is Methyl 4-ethoxybenzoate, 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. category: esters-buliding-blocks

General procedure: To a suspension of sodium hydride (60% in mineral oil, 5 eq) in dryTHF was added solution of substituted methyl benzoate (2 eq) in dryTHF. After mixture refluxed, substituted acetophenone (1 eq) in dryTHF was added dropwise. The mixture was refluxed overnight, then quenched with 1 N HCl. The mixture was extracted with ethyl acetatetwice, and the combined organic phase was washed with brine solution,dried with anhydrous Na2SO4, filtrated, and concentrated under reduced pressure. The residue was purified on a silica gel column.

The synthetic route of 23676-08-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jeong, Jieun; Kim, Kun-Hee; Kim, Dong-Young; Chandrasekaran, Gopalakrishnan; Kim, Minhee; Pagire, Suvarna H.; Dighe, Mahesh; Choi, Eun Young; Bak, Su-Min; Kim, Eun-Young; Shin, Myung-Geun; Choi, Seok-Yong; Ahn, Jin Hee; Bioorganic and Medicinal Chemistry; vol. 27; 19; (2019);,
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