Tag: M.W=200-300

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. 31273-66-2, name is Ethyl 2,3-dichlorobenzoate, A new synthetic method of this compound is introduced below., name: Ethyl 2,3-dichlorobenzoate

General procedure: In a fume hood, an oven dried Schlenk flask equipped with a magnetic stirring bar was filled with N2 and evacuated (three cycles). Under N2 atmosphere [Ir(OMe)(COD)]2 (13.3 mg, 0.01 mmol, 1 mol%), 4,4-ditert-butyl-2,2?-bipyridyl (10.7 mg, 0.02 mmol, 2 mol%), and pinacolborane (HBPin) (436 muL, 384 mg, 3 mmol, 1.5 equiv) were added. The appropriate arene substrate (2 mmol, 1 equiv) was added via micropipette under N2 atmosphere. The Schlenk flask was closed and the reaction mixture was heated at 80 C in an oil bath. The progress of reaction was monitored by GC-MS and TLC. Upon completion of reaction, Schlenk flask was cooled to r.t. and exposed to air. The contents of the flask were dissolved in CH2Cl2 (3-5 mL) and taken out in a round-bottomed flask. The volatile organics were removed under reduced pressure using a rotary evaporator. The crude product was purified by column chromatography (silica gel, hexanes-CH2Cl2 1:1).

The synthetic route of 31273-66-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shahzadi, Tayyaba; Saleem, Rahman S. Z.; Chotana, Ghayoor A.; Synthesis; vol. 50; 21; (2018); p. 4336 – 4342;,
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Related Products of 87808-49-9,Some common heterocyclic compound, 87808-49-9, name is Methyl 2-bromo-4-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.

Step 1: Preparation of 3-(2-bromo-4-methylphenyl)pentan-3-ol To a solution of methyl 2-bromo-4-methylbenzoate (10 g, 43.7 mmol) in THF (10 mL) was added dropwise EtMgBr (88 mL, 262 mmol) at 0 C. under nitrogen and then stirred at rt for 12 h. The reaction mixture was quenched with NH4Cl-saturated water and extracted with EA. The combined organic layer was washed with NaHCO3 solution and brine, dried over Na2SO4. The solution was concentrated and the residue was purified by column chromatography over silica gel eluted with PE-EA (10:1?2:1) to provide 3-(2-bromo-4-methylphenyl)pentan-3-ol (8.09 g; yield 71.2%) as a white solid. 1H NMR (400 MHz, CDCl3): delta 7.67 (d, 1H), 7.52 (s, 1H), 7.23 (d, 1H), 2.35 (s, 3H), 1.83 (m, 4H), 0.77 (t, 6H) ppm.

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

Reference:
Patent; Anacor Pharmaceuticals, Inc.; Eli Lilly and Company; AKAMA, Tsutomu; Balko, Terry William; Defauw, Jean Marie; Plattner, Jacob J.; White, William Hunter; Winkle, Joseph Raymond; Zhang, Yong-Kang; Zhou, Yasheen; US2013/131017; (2013); A1;,
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Electric Literature of 260806-90-4, 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. 260806-90-4 name is Methyl 3-bromo-2-methoxybenzoate, 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.

To a solution of methyl-3-bromo-2-methoxylbenzoate 6 (1.5 g, 6.12 mmol) in 13 mL of anhydrous 1,4-dioxane were subsequently added bis(pinacolate)diboron (2.3 g, 9.18 mmol), potassium acetate (1.5 g, 15.3 mmol), followed by bis(diphenylphospinoferrocene)palladium dichloride (134.6 mg, 0.184 mmol). The resulting mixture was heated to 110 C in an oil bath for 2 h or to 130 C in a microwave reactor for 30 min (5 bar, 200 W). Afterwards, the solvent was removed under reduced pressure to afford the crude pinacol ester that was used in the following step without further purification. Then, ammonium acetate (1.4 g, 18.36 mmol) and sodium periodate (3.9 g, 18.36 mmol) were added to a solution of the crude pinacol ester in a mixed solution of acetone (11.0 mL) and water (11.0 mL). The resulting mixture was stirred at r.t. until complete conversion of the starting material was observed by TLC. The precipitate was then filtered off, and the filtrate was concentrated under reduce pressure. The residue was extracted with ethyl acetate, and the combined organic extracts were dried over anhydrous Na2SO4, filtered and evaporated. The crude product was finally purified by silica gel column chromatography (n-hexane/ethyl acetate 6:4) to give 2-methoxy-3-(methoxycarbonyl)phenylboronic acid 7 (938.6 mg, 4.47 mmol). Yield: 73%. 1H NMR (400 MHz, CDCl3) delta (ppm): 8.04 (dd, 1H, J = 7.4 Hz, J = 1.9 Hz, H4), 7.96 (dd, 1H, J = 7.8 Hz, J = 1.9 Hz, H6), 7.24 (t, 1H, J = 7.5 Hz, H5), 6.15 (bs, 2H, B(OH)2), 3.94 (s, 3H, OCH3), 3.92 (s, 3H, COOCH3).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-bromo-2-methoxybenzoate, and friends who are interested can also refer to it.

Reference:
Article; Bertini, Simone; Chicca, Andrea; Arena, Chiara; Chicca, Stefano; Saccomanni, Giuseppe; Gertsch, Juerg; Manera, Clementina; Macchia, Marco; European Journal of Medicinal Chemistry; vol. 116; (2016); p. 252 – 266;,
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Adding a certain compound to certain chemical reactions, such as: 54810-63-8, name is Methyl 2-chloro-5-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 54810-63-8, Recommanded Product: Methyl 2-chloro-5-methoxybenzoate

Methyl (2-chloro-5-methoxy)benzoate (18) (1.19 g, 6.47 mmol) was stirred vigorously in neat aqueous ammonia (28%, 7.8 mL) at room temperature. After 24 h, the resulting mixture was treated with chloroform and the separated organic phase washed with aqueous hydrochloric acid (5 M, 55 mL), water (40 mL), brine (40 mL) then dried (MgSO4), filtered and concentrated under reduced pressure to give 19 as a white powder (0.93 g, 78% yield). m.p. 125.3-126.9 C; IR (ZnSe): 3372, 3178, 1650, 1480, 1461, 1446, 1239, 1028, 821 cm-1; 1H NMR (300 MHz, MeOD): delta 7.34 (1H, d, J = 8.8 Hz), 7.05 (1H, d, J = 2.9 Hz), 7.00 (1H, dd, J = 2.9 and 8.8 Hz), 3.81 (3H, s) ppm; 13C NMR (75 MHz, MeOD): delta 172.1, 159.8, 137.9, 132.0, 122.8, 117.9, 115.2, 56.2 ppm; LRMS (GC-MS): 185 ([M], 60%), 169 ([M-NH2], 100%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-chloro-5-methoxybenzoate, and friends who are interested can also refer to it.

Reference:
Article; Callis, Timothy B.; Reekie, Tristan A.; O’Brien-Brown, James; Wong, Erick C.N.; Werry, Eryn L.; Elias, Nabiha; Jorgensen, William T.; Tsanaktsidis, John; Rendina, Louis M.; Kassiou, Michael; Tetrahedron; vol. 74; 12; (2018); p. 1207 – 1219;,
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Application of 6232-12-8,Some common heterocyclic compound, 6232-12-8, name is Ethyl 4-(aminomethyl)benzoate hydrochloride, molecular formula is C10H14ClNO2, 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.

4-Chloro-naphthalimidyl-methylbencoic acid- ethylester (2):; 20.0 g (93.2 mM) 4- aminomethylbencoic acid-ethylester hydrochloride , 21.68 g (93.2 mM) 4-Chloro-l,8-naphthalic anhydride and 19.78 g triethylamine (195.5 mM) in 400 ml DMF were heated to 900C and stirred overnight.[0044] After cooling to room temperature, 100 ml H2O were added to precipitate the desired product.[0045] The 4-Chloro-naphthalimidyl-methylbencoic acid-ethylester was recrystallized from EtOH. Yield: 15.8 g.[0046] The HPLC (Vydac 10-90- 15) shows a single peak at t = 14.04 and the mass peak MH+ = 394.8 ( M = 393.82) was found in the Matrix Assisted Laser Desorption/Ionization Time-of- Flight (MALDI-TOF) mass spectrum.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 4-(aminomethyl)benzoate hydrochloride, its application will become more common.

Reference:
Patent; ROCHE DIAGNOSTICS GMBH; F. HOFFMANN-LA ROCHE AG; WO2006/58778; (2006); A2;,
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Related Products of 264276-14-4,Some common heterocyclic compound, 264276-14-4, name is Dimethyl 2,6-dichloroterephthalate, molecular formula is C10H8Cl2O4, 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 the stirred solution of dimethyl 2,6-dichlorobenzene-1,4-dicarboxylate (2 g, 7.6 mmol, Step b) in tetrahydrofuran and water (1:1, 20 mL), sodium hydroxide (304 mg, 7.6 mmol) was added and the reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated under vacuum and the residue was neutralized using cold hydrochloric acid (1N). The precipitated solid was filtered under suction, washed with hexane and dried to afford 3,5-dichloro-4-(methoxycarbonyl)benzoic acid as an white solid (1.5 g, 85%). 1H NMR (400 MHz, DMSO-d6): delta 7.93 (s, 2H), 3.94 (s, 3H). MS: 247.6 (M-2), 249.6 (M).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Dimethyl 2,6-dichloroterephthalate, its application will become more common.

Reference:
Patent; Daiichi Sankyo Company, Limited; Verma, Ashwani Kumar; Nagaswamy, Kumaragurubaran; Sharma, Lalima; Ghosh, Soma; Kale, Balkrishna Ramchandra; Mondal, Aniruddha; Srivastava, Punit Kumar; Dastidar, Sunanda Ghosh; Momin, Rijwan Jaffer; Wagh, Pradip Balu; Pansare, Sonali Nanasaheb; Markad, Pramod Raosaheb; Khairnar, Yogesh Balasaheb; Miyauchi, Rie; Murata, Takeshi; Ishizaki, Masayuki; Nagamochi, Masatoshi; Iimura, Shin; US2014/155398; (2014); A1;,
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Related Products of 19063-56-0, The chemical industry reduces the impact on the environment during synthesis 19063-56-0, name is 7-Bromo-2H-chromen-2-one, I believe this compound will play a more active role in future production and life.

General procedure: A 10 mL vial equipped with a small magnetic stirring bar wascharged with the appropriate bromo O-hetarene (1.0 equiv, 100mg), Pd(OAc)2 (5 mol%), and CuI (1.0 equiv). Anhyd DMF (1 mL)and the appropriate 1,3-azole (2.0 equiv) were added, and thevessel was purged with N2 and sealed with a PEEK snap cap. Themixture was stirred for 5 min at r.t. before the vessel was placedin the microwave reactor and the mixture was heated to 140 Cwith stirring for the appropriate time (usually 1 h). The solutionwas then cooled to r.t., diluted with EtOAc (15 mL), washed withsat. aq NH4Cl (2 × 15 mL) and dilute aq Na2S2O3 (10 mL). Theaqueous phases were extracted with EtOAc (2 × 10 mL), and theorganic phases were combined and washed with sat. aq NH4Cl(10 mL) and brine. Some H2O was added if any solids precipitatedduring the extraction. The combined organic phases weredried (MgSO4), filtered, and concentrated. The residue was purifiedby column chromatography (silica gel).

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-Bromo-2H-chromen-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sipos, Zoltan; Konya, Krisztina; Synlett; vol. 29; 18; (2018); p. 2412 – 2416;,
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Synthetic Route of 894796-87-3,Some common heterocyclic compound, 894796-87-3, name is Methyl 4-amino-2-(trifluoromethyl)benzoate, molecular formula is C9H8F3NO2, 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 solution of compound 3b (20.30 g, 92.63 mmol) in 200 mL of methanol at 0 C. was slowly added dropwise a solution of liquid bromine (15.54 g, 97.26 mmol) in 200 mL of methanol. The resulting reaction solution was stirred at 0C for 1 hour and concentrated under reduced pressure to give a residue. The residue was diluted with 200 mL of ethyl acetate and 200 mL of saturated sodium bicarbonate solution, and then extracted with ethyl acetate (100 mL x 3). The combined organic phases were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give Compound 3c (27.00 g).

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-amino-2-(trifluoromethyl)benzoate, its application will become more common.

Reference:
Patent; Zhengda Tianqing Pharmaceutical Group Co., Ltd.; Nanjing Mingde Drug Discovery Co., Ltd.; Yao Yuanshan; Chen Bin; Chen Yuan; Li Ao; Xu Ran; Huang Zhensheng; Tian Dongdong; Li Hongwei; Yang Chengshuai; Li Jian; Chen Shuhui; (26 pag.)CN107987072; (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. 20026-96-4, name is Ethyl 3-(4-chlorophenyl)propiolate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

General procedure: A 25 mL Schlenk tube equipped with a magnetic stirringbar was charged with I2 (12.7 mg, 0.05 mmol), substituted thiol1 (0.5 mmol) and alkyne 2 (0.75 mmol). The tube was evacuatedtwice and backfilled with nitrogen, and DTBP (2.5 mmol)was added into the tube under nitrogen atmosphere. The tubewas sealed with a balloon and the mixture was stirred undernitrogen atmosphere at 110 C for 18 h. Upon completion of thereaction, the resulting solution was cooled to r.t., and thesolvent was removed with the aid of a rotary evaporator. Theresidue was purified by column chromatography on silica gel(PE-EtOAc) to give 3.

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:
Article; Yan, Kelu; Yang, Daoshan; Zhang, Mengqi; Wei, Wei; Liu, Yao; Tian, Laijin; Wang, Hua; Synlett; vol. 26; 13; (2015); p. 1890 – 1894;,
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Synthetic Route of 150319-83-8, A common heterocyclic compound, 150319-83-8, name is Methyl 2-(3-aminophenyl)acetate hydrochloride, molecular formula is C9H12ClNO2, 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.

(1) (3R,5S)-1-(3-acetoxy-2,2-dimethylpropyl)-7-chloro-5-(2,3-dimethoxyphenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid (1.0 g) obtained in Example 1-(1) was converted into acid chloride according to the method of Example 53, which was reacted with 3-aminophenylacetic acid methyl ester hydrochloride (0.43 g) to obtain 3-[[(3R,5S)-1-(3-acetoxy-2,2-dimethylpropyl)-7-chloro-5-(2,3-dimethoxyphenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl]acetyl]aminophenylacetic acid methyl ester (0.85 g) as a colorless amorphous powder. 1H-NMR (CDCl3) delta: 0.959 (3H, s), 1.024 (3H, s), 2.025 (3H, s), 2.812 (1H, dd, J=5.6, 14.1 Hz), 3.002 (1H, dd, J=7.2, 14.1 Hz), 3.538 (1H, d, J=14.2 Hz), 3.608 (2H, s), 3.620 (3H, s), 3.690 (3H, s), 3.732 (1H, d, J=11.2 Hz), 3.870 (1H, d, J=11.2 Hz), 3.894 (3H, s), 4.403 (1H, dd, J=5.8, 7.2 Hz), 4.564 (1H, d, J=14.2 Hz), 6.299 (1H, s), 6.645 (1H, d, J=2.0 Hz), 6.95-7.48 (9H, m), 7.847 (1H, br).

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; Kori, Masakuni; Miki, Takashi; Nishimoto, Tomoyuki; Tozawa, Ryuichi; US2003/78251; (2003); A1;,
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