Month: March 2021

10602-03-6, name is Ethyl 4-ethynylbenzoate, 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. Recommanded Product: 10602-03-6

General procedure: To a solution of 10S1 (0.10 g, 0.59 mmol), Pd(PPh3)4 (41 mg, 0.035 mmol), and CuI (34 mg,0.18 mmol) in degassed tetrahydrofuran/diisopropylamine (THF/DIPA) (5/1, v/v) (19 mL) was added2,5-diiodothiophene (DIT) (0.20 g, 0.59 mmol). The solution was stirred at 60 C for 5 h. After coolingto room temperature, the reaction mixture was diluted with dichloromethane and passed through Celiteto remove the metal catalyst. The solution was washed with 1 N HCl aqueous solution and water, andthen dried over Na2SO4. After removing the solvent by evaporation, the crude product was purified bysilica gel chromatography using hexane-dichloromethane (3/2, v/v) as the eluent to give the desiredproduct as a pale yellow solid (62 mg, 27% yield).

The synthetic route of 10602-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ikai, Tomoyuki; Shimizu, Sho; Kudo, Tomoya; Maeda, Katsuhiro; Kanoh, Shigeyoshi; Bulletin of the Chemical Society of Japan; vol. 90; 8; (2017); p. 910 – 918;,
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13412-12-9, name is Methyl 3-(methylamino)but-2-enoate, 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. Application In Synthesis of Methyl 3-(methylamino)but-2-enoate

General procedure: 1195 mg (9.25 mmol 1 eq.) 1 and 1000 mg (9.25 mmol 1 eq.) 1,4-benzoquinone is solved in 12 mL nitromethane. The mixture is left for 24 hrs (no stirring). Crystals of product precipitate. They were filtered, washed with nitromethane and recrystallized from EtOAc. Rf in PE+EtOAc 2+1: 0.2. Yellow solid, yield: 1300 mg, 64 %. Compound described in 2.

The synthetic route of 13412-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Schaefer, Anja; Burstein, Ethan S.; Olsson, Roger; Bioorganic and Medicinal Chemistry Letters; vol. 24; 8; (2014); p. 1944 – 1947;,
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Reference of 5941-55-9, The chemical industry reduces the impact on the environment during synthesis 5941-55-9, name is Ethyl (E)-3-Ethoxyacrylate, I believe this compound will play a more active role in future production and life.

To a mixture of 5-amino-1H-pyrazole-4-carbonitrile (10.00 g, 92.51 mmol) in DMF (350.00mL) was added ethyl (E)-3-ethoxyacrylate (13.34 g, 92.51 mmol) and Cs2CO3 (60.38 g, 185.02mmol). The mixture was stirred at 100C for 2 hrs. After LCMS showed the reaction was complete, the reaction mixture was cooled to 25C, then added to water (300 mL), acidified by HC1 (1 M) till pH = 4, then filtered. The filter cake was dried in vacuum to give 5-hydroxypyrazolo[1,5- ajpyrimidine-3-carbonitrile (10.00 g, yield: 67.5 1%) as a white 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, Ethyl (E)-3-Ethoxyacrylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; WENGLOWSKY, Steven, Mark; MIDUTURU, Chandrasekhar, V.; BIFULCO, Neil, Jr; KIM, Joseph, L.; (91 pag.)WO2017/87778; (2017); A1;,
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Synthetic Route of 24398-88-7, 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. 24398-88-7 name is Ethyl 3-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.

To a stirred mixture of a compound of formula V (1 eq), a boronic acid derivative of general formula VI (1.1 eq) and tetrakis(triphenylphosphine)palladium (0.03 eq) in an organic solvent (e.g. 1,2-dimethoxy-ethane) is added at room temperature aqueous 1 M sodium carbonate solution (2.5 eq), the reaction mixture is heated at 80 to 90 C. for around 18 h, cooled, poured into ice-water and extracted two times with ethyl acetate. The combined organic layers are washed two times with brine, dried (e.g. MgSO4) and evaporated. The crude product is further purified by flash chromatography on silica gel (ethyl acetate/n-heptane) and crystallization (e.g. dichloromethane/diethyl ether/n-heptane) to give compounds of general formulae Ia or Ib.Prepared from hexamethyldisilizane (16.5 mL, 79 mmol) and n-BuLi (48.4 mL, 77 mmol) in TBME (40 mL), then commercially available ethyl 3-bromobenzoate (7.55 g, 33 mmol) and tert-butyl acetate (4.86 mL, 36 mmol) in TBME (80 mL) according to the general procedure III. Obtained as a light yellow oil (9.934 g, 101%; 95% purity).

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

Reference:
Patent; Gatti McArthur, Silvia; Wichmann, Juergen; Woltering, Thomas Johannes; US2008/261957; (2008); 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. 4131-74-2, name is Dimethyl 3,3-Thiodipropionate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 4131-74-2

Chemistry The preparation of target compounds 9-28 was described in Schemes 1 and 2. Compounds 7a-d and 8a-e were synthesized according to the procedures reported previously by our group [18,19]. The different substituent of phenylamine reacted with triphosgene to get compound compounds 7a-d. 8a-e was synthesized from the different substituent of chlorobenzene through three steps. The key intermediates 4-(2-chloro-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidin-4-yl)morpholine (4a) and 2-chloro-4-morpholino-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidine 6,6-dioxide(4b) were synthesized according to the procedures reported previously by our group

The synthetic route of 4131-74-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lei, Fei; Sun, Chengyu; Xu, Shan; Wang, Qinqin; Ouyang, Yiqiang; Chen, Chen; Xia, Hui; Wang, Linxiao; Zheng, Pengwu; Zhu, Wufu; European Journal of Medicinal Chemistry; vol. 116; (2016); p. 27 – 35;,
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Electric Literature of 72594-86-6,Some common heterocyclic compound, 72594-86-6, name is Benzyl tert-butyl malonate, molecular formula is C14H18O4, 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 4: 1-Benzyl 3-tert-butyl 2-undecylmalonate To a suspension of NaH (160 mg, 4.0 mmol) in DMF (8 mL) at 0¡ã C. under N2, was added benzyl tert-butyl malonate (1.0 g, 4.0 mmol) in DMF (2 mL). The mixture was stirred for 50 min after which 1-bromoundecane in DMF (2 mL) was added. After an additional hour of stirring the reaction was allowed to warm to room temperature. The reaction was maintained overnight. Et2O (100 mL) and water (20 mL) were added to partition the reaction. The aqueous phase was extracted with Et2O (100 mL), and the combined organics dried over Na2SO4. The solvent was evaporated and the residue purified by flash column (C18 12 g, 40-100percent ACN/water+0.1percent TFA) to yield the title compound as a colorless oil (1.14 g, 2.82 mmol, 71percent): LCMS Method F Rt=1.58 min, M+Na 427.4; 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 0.84-0.96 (m, 3H) 1.28 (br. s, 12H) 1.31 (m, J=3.90 Hz, 6H) 1.41 (s, 9H) 1.88 (q, J=7.38 Hz, 2H) 3.29 (t, J=7.58 Hz, 1H) 5.19 (q, J=12.27 Hz, 2H) 7.30-7.42 (m, 5H).

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

Reference:
Patent; NOVARTIS AG; ZECRI, Frederic; GROSCHE, Philipp; YASOSHIMA, Kayo; ZHAO, Hongjuan; Yuan, Jun; USERA, Aimee Richardson; LOU, Changgang; KANTER, Aaron; BRUCE, Alexandra Marshall; Giumaraes, Carla; US2015/31604; (2015); A1;,
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Application of 15441-07-3, These common heterocyclic compound, 15441-07-3, name is Methyl 3-(chlorosulfonyl)propanoate, 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.

To a solution of Compound IE (40 mg, 0.092 mmol) and triethylamine (0.026 mL, 0.184 mmol) in CH2CI2 (1 mL) in an ice bath was added methyl 3- (chlorosulfonyl)propanoate (25.7 mg, 0.138 mmol). Upon completion of addition, the reaction mixture was stirred in the ice bath for 15 min. After this time, the reaction mixture was allowed to warm to rt, where it stirred for 3 h. At the conclusion of this period, the reaction mixture was quenched with saturated aq aHCOs (1 mL) and then extracted with CH2CI2 (3 x 2 mL). The combined organic layers were dried( a2S04), filtered, and concentrated to yield a residue. The residue was purified by column chromatography (silica gel, CELC^-EtOAc gradient 0 to 90% EtOAc) to afford Example 2 as a white solid (42 mg, 78% yield). XH NMR (500 MHz, DMSO- d6) delta ppm 8.24 (2H, s), 7.98 (IH, d, J=1.9 Hz), 7.64 (IH, d, J=8.5 Hz), 7.51 (IH, dd, J=8.5, 1.9 Hz), 6.20 – 6.26 (IH, m), 5.36 – 5.44 (IH, m), 4.15 – 4.23 (2H, m), 3.91 – 3.95 (2H, m), 3.62 (3H, s), 3.51 – 3.59 (2H, m), 3.46 (2H, t, J=5.6 Hz), 3.40 (2H, t, J=7.2 Hz), 2.74 (2H, t, J=7.2 Hz), 2.57 – 2.66 (2H, m), 2.38 (2H, t, J=7.4 Hz), 2.09 – 2.19 (2H, m), 1.70 – 1.81 (2H, m), 1.47 – 1.58 (2H, m), 0.88 (3H, t, J=7.3 Hz).LC/MS (m/z) = 586 (M+H)+.

The synthetic route of 15441-07-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YE, Xiang-Yang; WACKER, Dean A.; ROBL, Jeffrey A.; WANG, Ying; WO2011/140160; (2011); A1;,
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Synthetic Route of 17994-94-4, These common heterocyclic compound, 17994-94-4, name is Methyl 7-aminoheptanoate hydrochloride, 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.

Methyl 7-(2-trimethylsilanyl-ethoxycarbonylamino)-heptanoate Methyl 7-amino-heptanoate hydrochloride (7.0 g, 35.9 mmol) was dissolved in dichloromethane (75.4 mL), and N-[2-(trimethylsilyl)ethoxycarbonyloxy]succinimide (10.0 g, 38.6 mmol) and triethylamine (10 mL, 71.7 mmol) were then added at room temperature. The mixture was stirred for 5 hours, and then quenched with water (100 mL), and separated. The aqueous layer was extracted with dichloromethane (50 mL). The organic layers were combined, then dried over anhydrous sodium sulfate, and filtered. The solvent was distilled off under reduced pressure to obtain 8.89 g (29.3 mmol, 82% yield) of methyl 7-(2-trimethylsilanyl-ethoxycarbonylamino)-heptanoate. 1H-NMR (CDCl3) delta: 0.04 (9H, s), 0.97 (2H, br.t, J = 8.4 Hz), 1.20-1.76 (8H, m), 2.31 (2H, t, J = 7.4 Hz), 3.07-3.23 (2H, m), 3.67 (3H, s), 4.14 (2H, br.t, J = 8.4 Hz), 4.50-4.70 (1H, m)

Statistics shows that Methyl 7-aminoheptanoate hydrochloride is playing an increasingly important role. we look forward to future research findings about 17994-94-4.

Reference:
Patent; Chugai Seiyaku Kabushiki Kaisha; KOHCHI, Yasunori; NAKAMA, Kimitaka; KOMIYAMA, Susumu; WATANABE, Fumio; EP2886530; (2015); A1;,
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Synthetic Route of 64123-77-9, 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. 64123-77-9, name is Methyl 2-(3-fluorophenyl)acetate, This compound has unique chemical properties. The synthetic route is as follows.

Example 21: (R)-3-[l-(3-Fluoro-phenyl)-cycloheptanecarbonyloxy]-l-(5-phenyl- [l,3,4]oxadiazol-2-ylmethyl)-l-azonia-bicyclo[2.2.2]octane chloride a) 2-But-3-enyl-2-(3-fluoro-phenyl)-hex-5-enoic acid methyl ester (3-Fluoro-phenyl)-acetic acid methyl ester (4.30 g) was dissolved in tetrahydrofuran (20 mL) and cooled to -78C. Lithium zs(trimethylsilyl)amide (25.6 mL, IM THF solution) was added and the solution was stirred for 30 minutes. 4-Bromo-but-l-ene (2.60 mL) was added and the reaction was allowed to warm to room temperature and stirred for an hour. The reaction was again cooled to -78C. Lithium zs(trimethylsilyl)amide (25.6 mL, IM THF solution) was added and the solution was stirred for 30 minutes. 4-Bromo-l-butene (2.60 mL) was added and the reaction was allowed to warm to room temperature and stirred for an hour. The reaction was again cooled to -78C and further aliquots of Lithium zs(trimethylsilyl)amide (25.6 mL, IM THF solution) and 4-bromo-l-butene (2.60 mL) were added following the procedure outlined above. After stirring overnight, water (20 mL) was added and the reaction mixture extracted with diethyl ether (2 x 60 mL). The combined organic extracts were dried with magnesium sulfate and evaporated. The resulting liquid was purified by column chromatography on silica eluting with ethyl acetate / iso hexane (1 / 99) to afford the sub-titled compound (5.0 g).m/e 277 [M+H]+

The chemical industry reduces the impact on the environment during synthesis Methyl 2-(3-fluorophenyl)acetate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; ARGENTA DISCOVERY Ltd.; FORD, Rhonan; WO2009/139709; (2009); A1;,
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Application of 185312-82-7, These common heterocyclic compound, 185312-82-7, name is Methyl 4-bromo-2-chlorobenzoate, 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.

The product from Example 143 Part A (1.0 g, 4.0 mmol), Zn (CN)2 (0.52 g, 4.8 mmol), Pd (PPh3)4 g, 0.2 mmol) were added together with 9 mL of DMF. The mixture was degassed and then heated at 90 C for 6 h. Water and EtOAc were added to the reaction mixture. It was filtered to remove inorganic solids. The layers were separated and the EtOAc layer was washed with water and brine. It was dried over MgS04, concentrated, and purified by flash chromatography (silica, EtOAc/hexane) to give 0.28 g of the desired product. MS: 196.1 (M+1)+.

Statistics shows that Methyl 4-bromo-2-chlorobenzoate is playing an increasingly important role. we look forward to future research findings about 185312-82-7.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2005/123050; (2005); A2;,
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