Month: December 2020

13831-03-3,Some common heterocyclic compound, 13831-03-3, name is tert-Butyl propiolate, molecular formula is C7H10O2, 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.

Example 9 Methyl (E)-3-[[1-(pyridin-3-yl)naphthalen-2-yl]oxy]acrylate 1-(Pyridin-3-yl)naphthalen-2-ol (80 mg, 0.26 mmol) obtained in Example 8 (1) was dissolved in dimethylformamide (2 mL), sodium hydride (16 mg, 0.4 mmol) was added thereto in an ice bath, and the solution was stirred at room temperature. After 10 minutes, methyl propiolate (91 muL, 1.1 mmol) was added to the reaction solution and the reaction solution was further stirred at 110 C. After 16 hours, water was added to the reaction solution in an ice bath, extraction was carried out using chloroform, the organic layer was dried over sodium sulfate and filtered, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate_hexane=1:2) to obtain a crude material of methyl (E)-3-[[1-(pyridin-3-yl)naphthalen-2-yl]oxy]acrylate (25 mg, yield of 22%) and methyl (Z)-3-[[1-(pyridin-3-yl)naphthalen-2-yl]oxy]acrylate. j0682] A title compound (white crystal, 24 mg, yield of41%) was obtained according to the same method as inExample 9 using 4-(2-mercaptonaphthalen- 1 -yl)benzonitrile(40 mg, 0.15 mmol) obtained in Example 48 (3) and t-butylpropiolate (63 pL, 0.46 mmol).10683] ?H NMR (CDC13, 400 MHz): oe=1.43 (s, 9H), 5.46(d, 1H, J=15 Hz), 7.32 (d, 1H, J=8 Hz), 7.4-7.5 (m, 3H),7.5-7.6 (m, 2H), 7.63 (d, 1H, J=8 Hz), 7.78 (d, 2H, J=8 Hz),7.9-8.0 (m, 2H).

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

Reference:
Patent; J-Pharma Co., Ltd.; Endo, Tsuyoshi; Kobayashi, Kunio; Tanaka, Hiroto; Saito, Daisuke; Hirano, Masaharu; Endou, Hitoshi; Anzai, Naohiko; (68 pag.)US2017/290795; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 792-74-5, name is Dimethyl [1,1′-biphenyl]-4,4′-dicarboxylate, 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 792-74-5, 792-74-5

a) Preparation of 4,4′-bis (Hydroxy-Methyl) Biphenyl. 789mg (20.8 mmoles) of LiAlH4 in 150ml of anhydrous THF (tetrahydrofuran) are placed in a 2-litre flask which has a mechanical agitator, cooler, filler funnel and heating bath. A solution, heated to 50oC, of 7.5g (27.7 mmoles) of 4,4′-bis (methoxycarbonyl)biphenyl in 500ml of anhydrous THF is added dropwise, over a period of 1 hour, to the mixture, heated in an inert atmosphere to 50oC under agitation. After a further 30 minutes of agitation in a heating bath, the mixture is cooled to ambient temperature and the excess LiAlH4 is destroyed by the careful addition of 15ml of a THF/H2O (80:20) mixture. The reaction mixture is filtered on Septum G2, washing the precipitate with anydrous ethanol (3x100ml). The combined filtrate and washings are evaporated to dryness under vacuum with the heating bath at 40oC. The residue is then redissolved with 100ml of hot acetone (50oC), eliminating the insoluble residue by filtration, dried on anhydrous Na2SO4 and evaporated to dryness. 5.74g of 4,4′-bis (hydroxymethyl) biphenyl are obtained with a molar yield of 96.6percent.

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, Dimethyl [1,1′-biphenyl]-4,4′-dicarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ENIRICERCHE S.p.A.; EP469682; (1992); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 4606-07-9, name is Ethyl cyclopropanecarboxylate, A new synthetic method of this compound is introduced below., 4606-07-9

(a) Bis(4-methoxyphenyl)cyclopropylcarbinol: The Grignard reagent was prepared from 12.7 g (0.53 mol) of magnesium filings and 93.5 g (0.50 mol) of 4-bromoanisole in 160 ml of absolute ether. 26.0 g (0.228 mol) of ethyl cyclopropanecarboxylate were slowly added dropwise to this solution and the mixture was then heated at the reflux temperature for 2.5 hours. The reaction solution was poured onto ice and diluted with about 300 ml of saturated ammonium chloride solution, so that the resulting precipitate dissolved. The solution was then extracted with ether and the ethereal phase was washed with water, dried and concentrated. Vacuum distillation of the crude product gave 39.2 g of a fraction at 195-200 C./0.18 mm Hg.

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; Hoechst Aktiengesellschaft; US4918073; (1990); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

14062-25-0, Name is Ethyl 2-(4-bromophenyl)acetate, 14062-25-0, 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.

Example 26; 2-(4-Bromo-phenyl)-acrylic acid ethyl esterTo a solution of (4-bromo-phenyl)-acetic acid ethyl ester (972.4 mg, 4 mmol), paraformaldehyde (240 mg, 8 mmol), and Bu4NCl (22 mg, 0.08 mmol) in DMF (10 mL) was added K2CO3 (1.32 g, 9.6 mmol). This mixture was heated at 60 degrees Celsius for 2 h. Then the mixture was cooled and diluted with EtOAc (30 mL) and washed with water (20 mL¡Á3), brine, dried over Na2SO4, filtered and evaporated. The residue was purified by flash column chromatography on silica gel to give a white solid (0.74 g, 73%). MS: calc’d 255 (MH+), exp 255 (MH+).

Statistics shows that Ethyl 2-(4-bromophenyl)acetate is playing an increasingly important role. we look forward to future research findings about 14062-25-0.

Reference:
Patent; Liang, Chungen; Tang, Guozhi; Wong, Jason Christopher; Wu, Xihan; US2010/69328; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

A common compound: 61367-07-5, name is Methyl trans-4-aminocyclohexanecarboxylate hydrochloride, 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. 61367-07-5

Example 14 4-{4-[4-(3-Methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid methyl ester 1-(2-Chloro-pyrimidin-4-yl)-4-(3-methanesulfonyl-propoxy)-1H-indole (300 g), 4-amino-cyclohexanecarboxylic acid ethyl ester HCl salt (155 g), and K2CO3(170 g) in NMP (2.35 L) were stirred at 80 C. for 5 h and then stirred overnight at room temperature. The reaction mixture was then stirred on an ice bath, and 2.5 L water was slowly added while stirring, and cooling continued until completion of the exothermic reaction. Upon cooling, the mixture was filtered, and resulting solid was rinsed with H2O and dried in vacuo overnight to yield 4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid methyl ester (97%).

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, 61367-07-5, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Arzeno, Humberto Bartolome; Filonova, Lubov K.; Goldstein, David Michael; Gong, Leyi; Loe, Bradley E.; O’Brien, Erin M.; Palmer, Wylie Solang; Rotstein, David Mark; Silva, Tania M.; Tan, Yun-Chou; US2011/301171; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 89-91-8, name is Methyl 2,2-dimethoxyacetate, molecular formula is C5H10O4, 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. 89-91-8

To a solution of methyl 2,2-dimethoxyacetate (8.7 g, 64.9 mmol, 7.98 mL, 1 eq) in dioxane (50 mL) and H20 (50 mL) was added LiOH H20 (3.27 g, 77.8 mmol, 1.2 eq) at 0 C . After addition, the mixture was stirred at this temperature for 1 h, and then the resulting mixture was stirred at 20C for 10 h. TLC indicated that one new spot formed. The reaction mixture was diluted with NaOH aqueous solution (1 M, 80 mL), and extracted with petroleum ether (80 mL x 3). The combined aqueous layers were acidified with HC1 (6 M) aqueous solution to pH=l, and then extracted with ethyl acetate (80 mL for 3 times). The combined organic layers were dried over Na2S04, filtered and concentrated under reduced pressure to give 3.54 g of a colorless oil, which was used directly in the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 89-91-8, its application will become more common.

Reference:
Patent; SIGILON THERAPEUTICS, INC.; VEISEH, Omid; HEIDEBRECHT, Richard; WOTTON, Paul, Kevin; OBERLI, Matthias; MILLER, Robert, James; (498 pag.)WO2018/67615; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 87-24-1, name is Ethyl 2-methylbenzoate, 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 87-24-1, 87-24-1

General procedure: In a glove box, add a ruthenium complex Ia (0.3 to 0.7 mg, 0.0002 to 0.001 mmol) to a 300 mL autoclave,Potassium methoxide (35-700 mg, 0.5-10 mmol), tetrahydrofuran (4-60 mL), and ester compounds (10-200 mmol).After sealing the autoclave, take it out of the glove box and fill it with 50 100atm of hydrogen.The reaction kettle was heated and stirred in an oil bath at 100 C for 10 to 336 hours.After the reaction kettle was cooled in an ice-water bath for 1.5 hours, the excess hydrogen was slowly released.The solvent was removed from the reaction solution under reduced pressure, and the residue was purified with a short silica gel column to obtain an alcohol compound. The results are shown in Table 5.

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

Reference:
Patent; Zhejiang Zhongke Chuangyue Pharmaceutical Co., Ltd.; Ding Kuiling; Tang Yitian; Han Zhaobin; (55 pag.)CN110357923; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, A new synthetic method of this compound is introduced below., 25597-16-4

An Alternative Preparation of ethyl 3-(pyridin-2-yl)-4-(trifluoromethyl)isoxazole-5- carboxylate (IB); 1-B-l. Ethyl 2,3 -dibromo-4,4,4-trifluorobutanoate: Br 1 ,COOEtBr (1-B-l)[00110] Bromine (18.4 mL, 357 mmol) was added dropwise over 30 minutes to a solution of (E)-ethyl 4,4,4-trifluorobut-2-enoate (50 g, 297 mmol) in carbon tetrachloride (50 mL) at room temperature under nitrogen. The resulting dark red solution was refluxed for 4 hours. Additional bromine (2ml) was added and heating was continued until the HPLC analysis showed that the starting material had been consumed. The reaction mixture was concentrated under reduced pressure to give light brown oil which used in the next step without purification. HPLC (XBridge 5mu Cl 8 4.6×50 mm, 4 mL/min, Solvent A: 10 % MeOH/water with 0.2 % H3PO4, Solvent B: 90 % MeOH/water with 0.2 % H3PO4, gradient with 0-100 % B over 4 minutes): 2.96 and 3.19 minutes.

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; BRISTOL-MYERS SQUIBB COMPANY; PITTS, William, J.; DYCKMAN, Alaric, J.; SPERGEL, Steven, H.; WATTERSON, Scott, Hunter; WO2010/85582; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

51760-21-5, A common compound: 51760-21-5, name is Dimethyl 5-bromoisophthalate, 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.

PREPARATION 47 3-bromo-5-(methoxycarbonyl)benzoic acid To a solution of dimethyl 5-bromoisophthalate (2.80 g, 10.25mmols) in methanol (18.5 mL) was added a solution of potassium hydroxide (0.29 g, 5.13mmols) in 3.7 mL of water. The mixture was stirred overnight under reflux. The mixture was partitioned between water and ethyl ether. The aqueous phase was extracted twice with ether. The aqueous was then acidified to acid pH with 5N HCl and was extracted three times with ethyl ether. The combined organics were washed with brine and dried over sodium sulphate. Purification by chromatography (hexane 100% to ethyl acetate 100%) gave 0.700 g (2.70 mmol, 26%) of the title compound. HPLC/MS (10 min) retention time 5.79 min LRMS: m/z 259 (M-1)

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

Reference:
Patent; Almirall, S.A.; EP2394998; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

A common compound: 61644-18-6, name is Chloromethyl isobutyrate, 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. 61644-18-6

At room temperature,N-(3-(5-(4-Chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl)-propane-1-sulfonamide (0.1g, 0.2mmol)And triethylamine (57 muL, 0.40 mmol) was dissolved in DMF (1 mL).And add to it Chloromethyl isobutyrate(34 mg, 0.25 mmol).The reaction mixture was stirred at room temperature for 16 hr and then evaporated.The residue was purified by silica gel column chromatography ( petroleum ether / ethyl acetate (v/v) = 4/1 to 3/1).The title compound was obtained as a white solid (45 mg,37.5%).

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, 61644-18-6, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Wang Tingjin; Tang Yin; Sun Mingming; Wang Qian; (74 pag.)CN103626765; (2016); B;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics