Tag: M.W=200-300

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. 457097-93-7, name is Methyl 4-amino-3-(trifluoromethoxy)benzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 457097-93-7

[Step 1] 4-[(Methylsulfonyl)amino]-3-(trifluoromethoxy)benzoic acid To a solution of methyl 4-amino-3-(trifluoromethoxy)benzoate (600 mg) in chloroform (20 ml), triethylamine (2.12 ml) and methanesulfonyl chloride (0.795 ml) were added dropwise under ice-cooling. The reaction solution was stirred at 0 C. for 10 minutes and at room temperature for 2 hours. Saturated sodium bicarbonate water was added thereto, and the reaction solution was stirred at room temperature for 20 minutes and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was dissolved in methanol (20 ml). A 1 N aqueous solution of sodium hydroxide (20.4 ml) was added and the resultant reaction solution was stirred at 70 C. for one hour while heating. After the temperature of the solution was returned to room temperature and the reaction solution was concentrated up to about half under reduced pressure, 5 N hydrochloric acid (4 ml) was added dropwise. The precipitated solid was collected by filtration and dried under reduced pressure to obtain the title compound (740 mg) as a solid. 1H-NMR (DMSO-D6) delta: 3.17 (3H, s), 7.70 (1H, d, J=8.5 Hz), 7.81-7.84 (1H, m), 7.93 (1H, dd, J=8.9, 2.1 Hz), 10.25 (1H, s), 13.31 (1H, s). MS (ESI/APCI) m/z: 298 [M-1]-

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

Reference:
Patent; Daiichi Sankyo Company, Limited; Ota, Masahiro; Inoue, Hidekazu; Kawai, Junya; Ohki, Hitoshi; Toki, Tadashi; (25 pag.)US2019/284198; (2019); A1;,
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Application of 99548-55-7,Some common heterocyclic compound, 99548-55-7, name is Methyl 4-bromo-2-methylbenzoate, 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.

REFERENCE EXAMPLE 2; Methyl 4-bromo-2-(bromomethyl)benzoate; To a solution of methyl 4-bromo-2-methylbenzoate (9.60 g, 0.42 mol, obtained in reference example 1) in CCI4 (150 mL), Lambda/-bromosuccinimide (7.46g, 0.42mol) and benzoyl peroxide (0.19g, 0.79mmol) were added. The reaction mixture was stirred EPO 4h at room temperature while irradiated with a 250 Watt lamp and it was then filtered to remove the precipitated solids. The filtrate was washed with 1 N NaOH and water and it was dried over Na2SO4. The solvent was evaporated to afford11.87 g of the desired compound as an oil that solidified on standing (yield: 92%, uncorrected).1H NMR (300 MHz, CDCI3) delta (TMS): 3.94 (s, 3 H), 4.90 (s, 2 H)1 7.51 (dd, J = 8.4Hz1 J1 = 2.1 Hz, 1 H), 7.63 (d, J = 1.8 Hz, 1 H), 7.84 (d, J = 8.4 Hz, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-bromo-2-methylbenzoate, its application will become more common.

Reference:
Patent; J. URIACH Y COMPANIA S.A.; WO2007/339; (2007); A1;,
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Some common heterocyclic compound, 115118-68-8, name is Diisopropyl 3,3-dimethoxycyclobutane-1,1-dicarboxylate, molecular formula is C14H24O6, 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: 115118-68-8

Reference Example 3 3-Oxocyclobutane carboxylic acid To diisopropyl 3,3-dimethoxycyclobutane-1,1-dicarboxylate (760 g) obtained from Reference example 2, 20% of hydrochloric acid solution (3.2 L) was added and the mixture was refluxed for four days. After that, the reaction solution was extracted with ethyl acetate, and then the organic layer was dried over magnesium sulfate. Solids were removed, the filtrate was dried under reduced pressure to obtain the title product (700 g). 1H-NMR (CDCl3): 11.2 (1H, s), 3.41 (5H, m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 115118-68-8, its application will become more common.

Reference:
Patent; Asahi Kasei Pharma Corporation; US2009/298894; (2009); A1;,
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Application of 52727-57-8, The chemical industry reduces the impact on the environment during synthesis 52727-57-8, name is Methyl 2-amino-5-bromobenzoate, I believe this compound will play a more active role in future production and life.

Intermediate 108To a solution of methyl 2-amino-5-bromobenzoate (7.38 g, 32.0 mmol) and pyridine (6.3 mL, 81.5 mmol) in 100 mL of anhydrous CH2CL2, was added slowly methane sulfonylchloride (6.5 mL, 79.9 mmol). After stirring overnight, reaction mixture was quenched with 100 mL of IN HC1 (aq). Aqueous mixture was extracted with ethyl acetate (3×120 mL) and combined organic layers were washed 200 mL brine. Organics were dried (MgS04), filtered, and concentrated under reduced pressure to yield intermediate 108 as an off white solid. Silica gel column chromatography (0-30% Ethyl Acetate in Hexanes), yielded intermediate C-C (9.35 g, 95 %) as a white off- white solid.1 H-NMR (CDC13, 300 MHz): delta 10.4 (s, IH), 8.22 (s, IH), 7.63 (s, 2H), 3.96 (s, 3H), 3.05 (s, 3H) LCMS m/z [M+H]+ C9Hi0BrNO4S requires: 307.95. Found 308.06

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-5-bromobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GILEAD SCIENCES, INC.; BABAOGLU, Kerim; BOOJAMRA, Constantine, G.; EISENBERG, Eugene, J.; HUI, Hon Chung; MACKMAN, Richard, L.; PARRISH, Jay, P.; SANGI, Michael; SAUNDERS, Oliver, L.; SIEGEL, Dustin; SPERANDIO, David; YANG, Hai; WO2011/163518; (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. 685892-23-3, name is Methyl 2-bromo-6-chlorobenzoate, A new synthetic method of this compound is introduced below., Product Details of 685892-23-3

A mixture of methyl 2-bromo-6-chlorobenzoate (750 mg, 3 mmol), (PPh 3) 4 Pd (345 mg, 0.3 mmol) and cyclobutyl zinc bromide (0.5 M in THF, 12 mL) was mixed under N 2 protection. The mixture was stirred under N 2 at 70 C. for 12 h. The mixture was extracted with EtOAc and water. The organic phase was washed with brine, dried over Na 2 SO 4, filtered and concentrated. The residue was purified by flash chromatography (PE: EtOAc = 50: 1) to give the title compound.

The synthetic route of 685892-23-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mrck Sharp and Dohme Corp; Blair T, Lapointe; Peter H, Fuller; Hakan, Gunaydin; Kun, Liu; Daneille F, Molinari; Qinglin, Pu; Mark E, Scott; B Wesely, Trotter; Hongjun, Zhang; (117 pag.)JP2018/531957; (2018); A;,
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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. 820236-81-5, name is Methyl 2-bromo-6-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 820236-81-5

[00500] Methyl 2-bromo-6-fluorobenzoate (38) (11.29 g, 48.5 mmol), cyclopropylboronic acid (6.24 g, 72.7 mmol), K3P04 (30.85 g, 145.4 mmol) and Pd(PPh3)4 (2.80 g, 2.4 mmol) were mixed under argon in a degassed mixture of toluene and water (20: 1, 160 mL). The resulting brown suspension was heated at reflux for 2.5 h, cooled, filtered through Celite, and evaporated. The residue was partitioned between ethyl acetate (150 mL) and brine (150 mL). The layers were separated and organic layer was dried over magnesium sulfate and evaporated. The oily residue was suspended in hexane and the solid was removed by filtration. Evaporation of the filtrate afforded the title compound (9.30 g, 47.9 mmol, 99%) as a light brown oil.

According to the analysis of related databases, 820236-81-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AFRAXIS, INC.; CAMPBELL, David; DURON, Sergio, G.; WO2013/86451; (2013); A2;,
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Application of 40546-94-9, 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. 40546-94-9, name is 6-Methyl-4-phenylchroman-2-one, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 2 3,4-Dihydro-6-methyl-4-phenyl-2H-benzopyran-2-ol (IV) 3,4-Dihydro-6-methyl-4-phenyl-2H-benzopyran-2-one (III, EXAMPLE 1, 100.0 g, 420.2 mmol) is added to toluene (500 mL). The mixture is degassed by purging alternately with vacuum and nitrogen and then cooled to -21. Diisobutylaluminumhydride in toluene solution (DIBAL, 1.5 M, 290 mL, 435 mmol) is then slowly added over 2 hr via add funnel while maintaining the reaction temperature at -20 to -25. The reduction is usually done when the DIBAL add is completed. If the reaction is not done additional DIBAL can be added in increments. When the reaction is done (<1% lactone) ethyl acetate (45 mL) is added at -20 to -25 via add funnel. Very little exotherm is observed. Next, citric acid (23%, 500 mL) is added. The mixture is stirred at 45-50 for 1 hr (or stirred overnight at 20-25), the phases are separated, the organic phase is washed with water (2 x 300 mL). The organic phase is concentrated to 250 mL under reduced pressure. Methanol (500 mL) is added, and the mixture is concentrated to 250 mL. The methanol addition and distillation is repeated to give the title compound in methanol solution. This solution is concentrated to a thick oil which crystallizes on standing to give the title compound (as a mixture of diastereomers), IR (neat) 3410, 3020, 2925, 1605, 1498, 1447, 1205 and 1010 cm-1; MS (m/z, EI) = 240 (parent). Rather then isolating and characterizing the title compound, it is normally taken directly into the next step. HPLC (column = zorbax C-8; mobile phase acetonitrile/water (50/50); flow rate = 1 mL/min; wavelength = 240 nm; note - the absorbance of the lactone (III) at 240 nm is approximately 3.5 times greater than the lactol (IV);. The chemical industry reduces the impact on the environment during synthesis 6-Methyl-4-phenylchroman-2-one. I believe this compound will play a more active role in future production and life. Reference:
Patent; PHARMACIA & UPJOHN COMPANY; EP960109; (2002); B1;,
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Adding a certain compound to certain chemical reactions, such as: 59247-47-1, name is tert-Butyl 4-bromobenzoate, 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 59247-47-1, name: tert-Butyl 4-bromobenzoate

To a 50 mL round-bottom flask purged and maintained under an inert atmosphere of nitrogen was added (1S,4S,5R)-5-[[4-cyclopropyl-l-(2,6-dichlorophenyl)-1H-pyrazol-5- yl]methoxy]-2-azabicyclo [2.2.1] heptane li (200 mg, 0.53 mmol, 1.00 equiv.), toluene (5 mL), Pd(OAc)2 (25 mg, 0.11 mmol, 0.20 equiv.), Xantphos (64 mg, 0.11 mmol, 0.20 equiv), Cs2CO3 (518 mg, 1.59 mmol, 3.00 equiv.), and tert-butyl 4-bromo-2-fluorobenzoate (134 mg, 0.49 mmol, 1.10 equiv.). The resulting mixture was heated at 90¡ãC overnight and concentrated under vacuum. The residue was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (1/3) to give tert-butyl 4-[(1S,4S,5R)-5-[[4-cyclopropyl-l-(2,6- dichlorophenyl)-1H-pyrazol-5-yl]methoxy]-2-azabicyclo[2.2.1] heptan-2-yl]-2-fluorobenzoate 2a (176 mg, 58percent) as a yellow solid

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

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; (231 pag.)WO2019/55808; (2019); A1;,
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Reference of 1186-73-8, The chemical industry reduces the impact on the environment during synthesis 1186-73-8, name is Trimethyl methanetricarboxylate, I believe this compound will play a more active role in future production and life.

Step 5; methyl 9-chloro-l-(2,4-dimethoxybenzyl)-4-hydroxy-2-oxo-l,2,5,6- tetrahydrobenzo [2,3] oxepino [4,5-b] pyridine-3-carboxylate A solution of N-(8-chloro-3 ,4-dihydrobenzo [b] oxepin-5 (2H)-ylidene)- 1 -(2,4- dimethoxyphenyl)methanamine (4.4 g crude) and trimethyl methanetricarboxylate (4.9 g, 25.6 mmol) in Pl^O (13 mL) was heated at 230 C for 15 min. The reaction mixture was cooled to room temperature, and purified on silica gel using EtO Ac/Hex (0-60% gradient) to afford the product (2.6 g, 43%) as a yellow foam. XH NMR (500 MHz, CHCl3-i/) delta ppm 2.06 – 2.17 (m, 1 H) 3.18 (dd, J=15.09, 3.90 Hz, 1 H) 3.63 – 3.68 (m, 3 H) 3.75 – 3.79 (m, 3 H) 3.99 (s, 3 H) 4.37 (dd, J=9.81, 6.34 Hz, 1 H) 4.41 – 4.50 (m, 1 H) 4.93 – 5.04 (m, 1 H) 5.15 (d, J=15.76 Hz, 1 H) 6.32 – 6.44 (m, 2 H) 6.94 (d, J=8.35 Hz, 1 H) 7.06 – 7.12 (m, 2 H) 7.17 (s, 1 H) 13.80 (s, 1 H). LC-MS: 470.1 [M-H]”, RT 1.45 min.

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, Trimethyl methanetricarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PTC THERAPEUTICS, INC.; BRANSTROM, Arthur; JOSYULA, Vara Prasad, Venkata Nagendra; ARNOLD, Michael, Andrew; GERASYUTO, Aleksey, I.; KARP, Gary; WANG, Jiashi; WO2013/33228; (2013); A1;,
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Application of 681465-85-0, 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. 681465-85-0, name is Methyl 4-amino-3-isopropoxybenzoate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The aryl carboxylic acid monomer (6 mmol, comp. 4-6), Mukaiyama reagent (6 mmol) and Et3N (12 mmol) were dissolved in an anhydrous dichloromethane (100 mL). The solution was refluxed for 15 min. under N2. Then a solution of the corresponding arylamine (5 mmol, comp. 7-9) in an anhydrous dichloromethane (20 mL) was added to the reaction mixture and resulting solution was refluxed for 2 days. The solvent was evaporated under vacuum and the residue was subjected to the column of silica gel using the mixture of hexanes/ dichloromethane (2:3) as an eluent to give amide coupling products in moderate to good yields. Note: for the synthesis of 18, 2.5 eq. of corresponding aryl amine over 2-methoxyisophthalic acid was used.

The chemical industry reduces the impact on the environment during synthesis Methyl 4-amino-3-isopropoxybenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Kulikov, Oleg V.; Incarvito, Christopher; Hamilton, Andrew D.; Tetrahedron Letters; vol. 52; 29; (2011); p. 3705 – 3709;,
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