Tag: M.W=200-300

These common heterocyclic compound, 148547-19-7, name is Methyl 4-bromo-3-methylbenzoate, 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. 148547-19-7

A suspension of methyl 4-bromo-3-methylbenzoate (ABCR AV19078; 15 g; 65.48 mmol; 1 eq.), o-tolylboronic acid (Aldrich 393606; 10.68 g; 78.5 mmol; 1.2 eq.), potassium carbonate (45.25 g, 327.4 mmol, 5 eq.) and tetrakis(triphenylphosphine)palladium(0) (3.78 g; 3.27 mmol; 0.05 eq.) in toluene (200 ml_) and water (200 ml_) was stirred at 12O0C for 6 hours. The resulting mixture was allowed to return to room temperature and the two phases were separated. The organic layer was concentrated in vacuo and purified by column chromatography (c-hexane) to afford the title compound (15 g, 95%) as a white solid.HPLC (Method B) : Rt 3.01 min (purity 98.7%). 1H NMR (DMSOd6, 400MHz) delta 7.91 (1 H, s), 7.83-7.81 (1 H, m), 7.33-7.30 (2H, m), 7.28-7.26 (1 H, m), 7.25-7.22 (1 H, m), 7.07-7.05 (1 H, d), 3.86-3.81 (3H, s), 2.09-2.00 (3H, s), 1.97-1.92 (3H, s).

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 148547-19-7.

Reference:
Patent; MERCK SERONO S.A.; WO2009/43890; (2009); A1;,
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110661-91-1, A common compound: 110661-91-1, name is tert-Butyl 4-bromobutanoate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Exemplification of General Procedure J:; Preparation of tert-butyl 4-(4-(3-(3-chloro-4-isopropoxyphenyl)-l,2,4-oxadiazol-5-yl)- lH-indol-l-yl)butanoate; To a solution of 3-(3-chloro-4-isopropoxyphenyl)-5-(lH-indol-4-yl)-l,2,4-oxadiazole (0.100 g, 0.283 mmol) in DMF (0.999 ml) was added NaH (0.012 g, 0.311 mmol). After about 15 min tert-butyl 4-bromobutanoate (0.095 g, 0.424 mmol) was added and the reaction mixture was heated to about 500C. After about 24h the reaction mixture was cooled to ambient temperature, concentrated in vacuo and purified by chromatography on silica gel (eluting with EtOAc/Hep) to provide tert-butyl 4-(4-(3-(3-chloro-4-isopropoxyphenyl)-l,2,4-oxadiazol-5- yl)-lH-indol-l-yl)butanoate (0.135 g, 93%) as a colorless oil that solidified on standing. LCMS (Table 1, Method c) Rt = 3.50 min, m/z 496 (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 4-bromobutanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBOTT LABORATORIES; WO2008/76356; (2008); A1;,
Ester – Wikipedia,
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619-42-1, 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 619-42-1 as follows.

EthynyHrimethylsilane (82.4 g. 0.84 rnol. 1.2 equiv) was added dropwise over 10 min under a nitrogen atmosphere to a soiution of methyl 4-brornobenzoate (150 g, 0.7 mol 1.0 equiv), PdC2 iPP h), (15 g, 0.021 mot.. 0.03 equiv) and Cul (13 g, 0.068 mol, 0.1 equiv) in TEA (1.5 L), The reaction was stired at 90C for 30 minutes, whereupon LCMS showed complete consumption of methyl 4-bromobenzoate. Then, the reaction mixture was filtered and the filter cake was washed with EiOAe (5 x 500 rnLj, The filtrate was concentrated under reduced pressure to give a residue, which was distilled under reduced pressure to yield methyl 4~{{triroethyi8tiyi) ethynyl) benzoate (INT-1.2) as an off-white solid (156 g, 96%).

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

Reference:
Patent; ACHAOGEN, INC.; PATTERSON, Brian, D.; LU, Qing; AGGEN, James, Bradley; DOZZO, Paola; KASAR, Ramesh, Annasaheb; LINSELL, Martin, Sheringham; KANE, Timothy, Robert; GLIEDT, Micah, James; HILDEBRANDT, Darin, James; MCENROE, Glenn, A.; COHEN, Frederick; WO2013/170030; (2013); A1;,
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99548-54-6, Name is Methyl 3-bromo-2-methylbenzoate, 99548-54-6, 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.

Preparation Example 13 Under a nitrogen atmosphere, a mixture of methyl 3-bromo-2-methylbenzoate (53.00 g), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane (88.10 g), bistriphenylphosphine palladium chloride (8.12 g), triphenylphosphine (6.07 g), potassium acetate (68.10 g), and dioxane (530 mL) was heated and stirred at 100 C. for 29 hours, and then cooled to room temperature. The reaction mixture was filtered through Celite and washed with ethyl acetate. The resulting filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain methyl 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (54.00 g) as a colorless oil.

Statistics shows that Methyl 3-bromo-2-methylbenzoate is playing an increasingly important role. we look forward to future research findings about 99548-54-6.

Reference:
Patent; Negoro, Kenji; Ohnuki, Kei; Yonetoku, Yasuhiro; Kuramoto, Kazuyuki; Urano, Yasuharu; Watanabe, Hideyuki; US2012/35196; (2012); A1;,
Ester – Wikipedia,
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183322-16-9, 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 183322-16-9 as follows.

1.6 Synthesis of ethyl 6-nitro-3,4-bis(methoxyethoxy)benzoateThe 0.23 mol ethyl 3,4-bis(methoxyethoxy)benzoate dissolved in 230 ml of acetic acid, maintaining the temperature of the systrem at 0-5C, 60 ml concentrated nitric acid was added. warmed to room temperature for 30 min, and continue reaction for 24h. The reaction mixture was poured into the 1000 ml water, ethyl acetate extraction (5¡Á250 ml), combined with the phase, are respectively using saturated NaHCO 3 solution (3x250mL) and saturated NaCl solution (3x250mL) washing, NaSO 4 drying. Activated carbon decolourizations, revolving off a solvent to obtain oil, yield 96%

According to the analysis of related databases, Ethyl 3,4-bis(2-methoxyethoxy)benzoate, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Beijing Normal University; Qi, Chuanmin; Wang, Xiao; Li, Shilei; He, Yong; Chen, Yurong; (16 pag.)CN103193722; (2016); B;,
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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 46064-79-3 as follows. 46064-79-3

Triethylamine (61 mg, 0.60 mmol) was added to a mixture of crude 2-methoxy-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid (110 mg, 0.5 mmol) (from Example 18 supra) and HATU (0.23 g, 0.6 mmol) (Aldrich) in DMF (5.0 mL) at room temperature. The resulting mixture was stirred until clear solution was obtained (light brown). Methyl 3-amino-4-bromobenzoate (0.14 g, 0.6 mmol) (Oakwood) was added. The mixture was stirred for another 20 hours. Precipitate formed. Water (50 mL), aqueous saturated sodium bicarbonate solution (10 mL), and ethyl acetate (30 mL) were added. After thorough mixing, pale yellow precipitate was collected by filtration, washed with water and ethyl acetate and dried in vacuum oven. Residue was recrystallized from DMF-ethyl acetate-hexanes to give product as pale yellow crystals. (Yield 0.04 g, 18.5%).HR-MS (ES+) m/z Calculated for C17H14BrN4O5 ([M+H]+): 433.0142. Found: 433.0143.

According to the analysis of related databases, 46064-79-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Anderson, Kevin; Chen, Yi; Chen, Zhi; Luk, Kin-Chun; Rossman, Pamela Loreen; Sun, Hongmao; Wovkulich, Peter Michael; US2012/184542; (2012); A1;,
Ester – Wikipedia,
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These common heterocyclic compound, 109232-37-3, name is Isobutyl 5-chloro-2,2-dimethylvalerate, 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. 109232-37-3

5-iodo-N-methyl-6-(methylsulfonamido)-2-p-tolylfuro[2,3-b]pyridine-3-carboxamide (136 mg, 0.28 mmol) and isobutyl 5-chloro-2,2-dimethylpentanoate (124 mg, 0.56 mmol) are dissolved in DMA (1 mL) and Cs2C03 (183 mg, 0.56 mmol) and Nal (42 mg, 0.28 mmol) added. The mixture is microwaved at 150 C for 20 min then diluted with water and extracted with EtOAc (3 x20 mL). The organic is then washed with Brine (10 mL) and dried over Na2S04 and concentrated. HPLC purification gives 70 mg (38% yield) of alkylated product isobutyl 5-(N-(5-iodo-3-(methylcarbamoyl)-2-p-tolylfuro[2,3-b]pyridin-6- yl)methylsulfonamido)-2,2-dimethylpentanoate. MS-ES [M + H]+ = 670.2. This compound is used directly in the next step.

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 109232-37-3.

Reference:
Patent; NOVARTIS AG; BARNES, David; CHOPRA, Rajiv; COHEN, Scott Louis; FU, Jiping; KATO, Mitsunori; LU, Peichao; SEEPERSAUD, Mohindra; ZHANG, Wei; WO2011/131709; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, molecular formula is C7H13BrO2, 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. 609-12-1

General procedure: To a solution of sodium methoxide (prepared from 0.1mol of sodium in anhydrous MeOH (60mL)), 0.05mol of 1 and 0.055mol of ester (2a-h) were added and refluxed 1-3h (chromatographic control TLC). The solvent was evaporated and the residue was dissolved in water and neutralized with HCl to pH=7-8. The product was extracted with CHCl3, dried, concentrated, and crystallized from diethyl ether.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 609-12-1, its application will become more common.

Reference:
Article; Studzi?ska, Renata; Ko?odziejska, Renata; Kupczyk, Daria; P?azi?ski, Wojciech; Kosmalski, Tomasz; Bioorganic Chemistry; vol. 79; (2018); p. 115 – 121;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, 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. 609-12-1

A) ethyl 2-(3-cyano-4-methoxy-2-oxopyridin-1(2H)-yl)-3-methylbutanoate (0774) A mixture of 4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile (5.0 g), ethyl 2-bromo-3-methylbutanoate (10.4 g), cesium carbonate (32.6 g) and N,N-dimethylformamide (75 mL) was stirred at 50C overnight. The reaction mixture was added to water, and the mixture was extracted twice with ethyl acetate. The extracts were combined, washed with water and then saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (6.11 g). MS (ESI+): [M+H]+ 279.2.

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 609-12-1.

Reference:
Patent; Takeda Pharmaceutical Company Limited; YOSHIDA, Masato; NAGAMIYA, Hiroyuki; OHBA, Yusuke; SETO, Masaki; YOGO, Takatoshi; SASAKI, Satoshi; TOKUNAGA, Norihito; ASO, Kazuyoshi; (298 pag.)EP2980089; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

A common heterocyclic compound, 154825-97-5, name is Methyl 2-(4-bromophenyl)-2,2-dimethylacetate, molecular formula is C11H13BrO2, 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. 154825-97-5.

EXAMPLE 12; 4 -R (1S)-1-[[(1S)-1-[[(1-cyanocyclopropyl)amino]carbonyl]-3-fluoro-3-methylbutyl]amino]-2,2,2- TRIFLUOROETHYLL-A, CT-DIMETHYL- (1, 1 -BI HENVLL-4-ACETIC acid; STEP 1 : 2- (4-BROMOPHENYL)-2-METHYLPROPANOIC acid; To a 0 C solution of diisopropylamine (1.52 mL) in THF (50 mL) was slowly added butyllithium (4.3 mL). The reaction mixture was stirred at 0 C for 15 minutes. It was cooled to-78 C and a solution of methyl 2- (4-bromophenyl) propanoate from Example 11 Step 2 (2.4 g) in THF (25 ML) was slowly added. The mixture was stirred at-78 C for 30 minutes. Then a solution of iodomethane (2.5 mL) in THF (25 mL) was added dropwise and the mixture was stirred at-78 C for 30 minutes then warmed up slowly to room temperature and stirred for 1 HOUR. H NMR showed 50% conversion. The reaction mixture was cooled to 0 C and 20 mL of potassium t-butoxid (1.0 M in THF) was added dropwise. The mixture was stirred at 0 C for 30 minutes, warmed up to room temperature and stirred for 1 hour. The reaction mixture was poured into ice (50 g) and saturated aqueous ammonium chloride (100 mL), extracted with ethyl acetate (3 x 100 mL). The combined extracts were washed with brine, dried with magnesium sulfate and the solvent removed in vacuo to yield a residue which was diluted with THF (30 ML) and methyl alcohol (15 mL). The solution was cooled to 0 C and 20 mL of lithium hydroxide (1.0 N) was added. The mixture was stirred at room temperature for 3 hours. Then the reaction mixture was poured into ice and 1N HC1 and extracted with dichloromethane (2 x 100 mL). The combined extracts were washed with brine, dried with magnesium sulfate and the solvent removed in vacuo. The residue was purified by swish using diethyl ether and hexanes to yield the title compound. ‘H NMR (CD3COCD3) 8 10.85 (1H, bs), 7.53 (2H, d), 7.48 (2H, d), 1.50 (6H, s).

The synthetic route of Methyl 2-(4-bromophenyl)-2,2-dimethylacetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK FROSST CANADA & CO.; WO2005/19161; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics