Tag: M.W=200-300

Synthetic Route of 19063-55-9, These common heterocyclic compound, 19063-55-9, name is 6-Bromochromen-2-one, 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.

It mainly includes the following steps: taking the coumarin derivative (500 mg, 2.2 mmol) after bromination at the 6 position,N,N-dimethylbenzene derivative (618 mg, 2.5 mmol) and K2CO3 (133 mg), which are introduced para-borate borate.The solution was dissolved in a toluene-ethanol mixed solution (3:1, 80 ml).After passing nitrogen gas for 30 min, 15 mg of tetrakistriphenylphosphine palladium catalyst was added to the solvent, and the mixture was heated to 80 C, 1000 r / min, and reacted for 8 hours.After the reaction, it was cooled to room temperature, washed with a large amount of water and extracted with dichloromethane.After removing excess solvent by a rotary evaporator, 100 mL of a dichloromethane solution was added to dissolve the solid, washed with 40 mL of distilled water, and separated.The remaining water was removed with anhydrous sodium sulfate, separated, and dried.The crude product was separated and purified on a 200-300 mesh silica gel column using dichloromethane-n-hexane (volume ratio 2:5) as eluent to afford yellow compound A as shown in Fig. 2.The coumarin-type organic nonlinear optical material compound A obtained by the above production method had a yield of 60%.

Statistics shows that 6-Bromochromen-2-one is playing an increasingly important role. we look forward to future research findings about 19063-55-9.

Reference:
Patent; Shantou University; Xu Liang; Zheng Yusen; Long Xueting; Zhang Wenying; Lu Fushen; (10 pag.)CN109776471; (2019); A;,
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Adding a certain compound to certain chemical reactions, such as: 110661-91-1, name is tert-Butyl 4-bromobutanoate, 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 110661-91-1, Safety of tert-Butyl 4-bromobutanoate

a) A mixture of 3-chloro-4-hydroxy-5-methyl-benzonitrile (1.15 g, 6.87 mmol) and Cs2CO3 (13.43 g, 41.2 mmol) in DMF (45 mL) is stirred at rt for 30 min before tert.-butyl 4-bromobutanoate (1.55 g, 6.95 mmol) is added. The orange suspension is stirred at 65 C. for 72 h. Another portion of tert.-butyl 4-bromobutanoate (1.55 g, 6.95 mmol) is added and stirring is continued at 65 C. for 24 h. The mixture is dilued with water (150 mL) and extracted three times with DCM (3*50 mL) and EA (3*50 mL). The org. extracts are combined, dried over MgSO4, filtered and concentrated. The crude product is purified by MPLC on silica gel eluting with heptane:EA:methanol to give tert-butyl 4-(2-chloro-4-cyano-6-methylphenoxy)butanoate (645 mg) as a colourless oil; LC-MS: tR=1.01 min, [M+H]+=no mass detectable; 1H NMR (D6-DMSO): delta 7.94 (d, J=1.7 Hz, 1H), 7.75 (d, J=1.3 Hz, 1H), 3.95 (t, J=6.3 Hz, 2H), 2.46 (t, J=7.2 Hz, 2H), 2.30 (s, 3H), 1.98 (quint, J=6.6 Hz, 2H), 1.41 (s, 9H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 4-bromobutanoate, and friends who are interested can also refer to it.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD.; Bolli, Martin; Lescop, Cyrille; Mathys, Boris; Morrison, Keith; Mueller, Claus; Nayler, Oliver; Steiner, Beat; US2013/303514; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 57381-59-6, name is Methyl 5-bromo-2-fluorobenzoate, 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 57381-59-6, COA of Formula: C8H6BrFO2

Example 2bExample la (1748 mg, 77% content, 1 1 ,80 mmol) is added to sodium hydride (60% suspension in mineral oil, 472 mg, 1 1.80 mmol) in THF (5 mL). Stirring is continued at room temperature for 45 min. Methyl 5-bromo-2-fluorobenzoate (1 100 mg, 4.72 mmol) in THF (5 mL) is added and stirring is continued at room temperature overnight. Example la (65 mg, 75% content, 0.43 mmol) is added to sodium hydride (60% suspension in mineral oil, 17 mg, 0.43 mmol) in THF (1 mL) and the resulting mixture added to the reaction mixture and stirring is continued at room temperature overnight. The reaction mixture is diluted with DCM, washed with saturated NH4CI, dried and concentrated under reduced pressure giving a residue. Trimethylsilyldiazomethane in hexanes (2M, 2.153 mL, 4.3 mmol) is added dropwise to the residue in DCM (5 mL) and MeOH (2.5 mL) cooled to 0C. Stirring is continued for 120 min, then the reaction mixture is evaporated under reduced pressure to furnish the title compound (200 mg, 50%> content, 7%>).HPLC-MS (Method 2): Rt = 1.38 minMS (ESI pos): m/z = 327 (M+H)+

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GIOVANNINI, Riccardo; BERTANI, Barbara; FERRARA, Marco; LINGARD, Iain; MAZZAFERRO, Rocco; ROSENBROCK, Holger; WO2013/17657; (2013); A1;,
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Application of 21597-54-6, The chemical industry reduces the impact on the environment during synthesis 21597-54-6, name is Methyl 3-amino-2-naphthoate, I believe this compound will play a more active role in future production and life.

40 g of compound A-1 (264 mmol) was added to a 500 ml three-necked flask, 16 g of formic acid and 160 ml of formamide were added, and the mixture was heated to 135 C for 5 h, and the reaction of the raw materials was completed by TLC; 200 ml of water was added, and the mixture was kept at 20 to 30 C for 1 h, and filtered. The filter cake was rinsed with water and recrystallized from ethanol to give 36.4 g of Compound A-2, yield 93.1%, purity 98.2%.

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 3-amino-2-naphthoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Yantai Jiu Mu Chemicals Co., Ltd.; Song Sisi; Chen Muxin; Li Xiangyang; Kong Xiangxing; Cui Lisha; (32 pag.)CN108178750; (2018); A;,
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Reference of 877149-10-5, 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. 877149-10-5, name is Methyl 4-bromo-2-chloro-6-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of methyl 4-bromo-2-chloro-6-methylbenzoate (1, 2.0 g, 7.6 mmol) in carbon tetrachloride (20 ml) were added N-bromosuccinimide (1.6 g, 9.1 mmol) and 2,2?-azobis(2-methylpropionitrile) (0.25 g, 1.52 mmol). The reaction mixture was stirred at 80¡ã C. for 12 h and progress of the reaction was monitored by TLC. After completion, solvent was diluted with dichloromethane and the organic layer was washed with water and brine. Following separation, the organic layer was dried using sodium sulphate and concentrated under reduced pressure to afford methyl 4-bromo-2-(bromomethyl)-6-chlorobenzoate (2) as a yellow sticky liquid. Yield: 3.9 g, crude.

The chemical industry reduces the impact on the environment during synthesis Methyl 4-bromo-2-chloro-6-methylbenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; EFFECTOR THERAPEUTICS, INC.; Sprengeler, Paul A.; Reich, Siegfried H.; Ernst, Justin T.; Webber, Stephen E.; (55 pag.)US2017/121339; (2017); A1;,
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Related Products of 179022-43-6, 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. 179022-43-6, name is Methyl 8-azabicyclo[3.2.1]octane-3-carboxylate hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

Example 6: 8-{l-[7-(cis-4-methyl-cyclohexyloxy)-8-trifluoromethyl-naphthalen-2-yl]-ethyl}-8-aza-bi cyclo[3.2.1]octane-3-carboxylic acid To a mixture of cesium carbonate (179 mg, 0.549 mmol) and 8-aza-bicyclo[3.2.1]octane-3-carboxylic acid methyl ester; HC1 salt (113 mg, 0.549 mmol) was added solution of 7-(l-bromo-ethyl)-2-(4-methyl-cyclohexyloxy)-l-trifluoromethyl-naphthalene (152 mg, 0.366 mmol) in N,N-dimethylformamide (4 mL, 50 mmol). The reaction mixture was stirred at rt for 30min, and heated at 50 C overnight. LCMS showed fairly clean Rt = 1.61min, m/z = 504.3. The mixture was diluted with MeOH, filtered to remove solid, and purified by HPLC (TFA method) to get the ester. The above ester was dissolved in MeOH (0.5mL) and THF (0.5 mL), added lithium hydroxide (0.0104 mL, 1.10 mmol) and water (0.5 mL) stirred at 50 C (hot plate) for lh. LC-MS shows the reaction was completed. Neutralized with concentarted HC1 solution, Prep HPLC gave product as a solid (32.7 mg, 18%). LCMS: Rt = 1.54 min, m/z = 490.3. 1H NMR (400 MHz, METHANOL-d4) delta 8.30 (s, 1H), 8.15 (d, J = 9.35 Hz, 1H), 8.08 (d, J = 8.47 Hz, 1H), 7.53 – 7.66 (m, 2H), 4.91 – 5.02 (m, 1H), 4.37 – 4.60 (m, 1H), 3.39 – 3.48 (m, 1H), 2.88 – 3.04 (m, 1H), 1.34 – 2.66 (m, 21H), 0.98 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis Methyl 8-azabicyclo[3.2.1]octane-3-carboxylate hydrochloride. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BIOGEN IDEC MA INC.; GUCKIAN, Kevin; KUMARAVEL, Gnanasambandam; MA, Bin; MI, Sha; PENG, Hairuo; SHAO, Zhaohui; SUN, Lihong; TAVERAS, Arthur; WANG, Deping; XIN, Zhili; ZHANG, Lei; WO2014/18881; (2014); A1;,
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Application of 106896-49-5,Some common heterocyclic compound, 106896-49-5, name is Methyl 4-amino-3-bromobenzoate, molecular formula is C8H8BrNO2, 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.

General procedure: Tert-butyl (R)-(5-(trimethylsilyl)pent-4-yn-2-yl)carbamate (160 mg, 0.63 mmol) was added in DMF (2.5 mL) to a sealed vial containing amino-halide (0.5 mmol), sodium carbonate (106 mg, 1.00 mmol), lithium chloride (21.00 mg, 0.50 mmol) and Pd(dppf)Cl2.CH2Cl2 (14.62 mg, 0.02 mmol). The reaction was degassed for 10 min, then heated to 100 C for 4 hours. After cooling, the reaction was diluted with EtOAc and washed with water and brine. The organic was dried over Na2SO4 and evaporated, then the crude product was purified by flash silica chromatography (EtOAc / heptane). Pure fractions were evaporated to dryness to afford the indole.

The synthetic route of 106896-49-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Moss, Thomas A.; Lister, Andrew S.; Wang, Jimmy; Tetrahedron Letters; vol. 58; 32; (2017); p. 3136 – 3138;,
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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. 756525-95-8, name is tert-Butyl 9-Amino-4,7-dioxanonanoate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: tert-Butyl 9-Amino-4,7-dioxanonanoate

To a solution of Z-Glu-OBz (0.5 g, 1.356 mmol) in CH2CI2 (3 mL) was added amino-DPEG2 t-buty ester (3 14 mg, 1.35 mmol), HATU (614 mg, 1.62 mmol), HO At (220 mg, 1 62 mmol) and TEA (0.563 ml, 4.04 mmol). The reaction mixture was stirred overnight at room temperature, diluted with EtOAc, and washed with brine (3x). The organic phase s dried over Na2S04, and concentrated. The crude product was purified on silica gel (ISCO, 40 g, 0-10 % MeOH / DCM eluent) to afford compound 74 (390 mg, 49.4 % yield). ESI MS: C31H42N2O9 (M+H) 587.3; found 587 3

According to the analysis of related databases, 756525-95-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERSANA THERAPEUTICS, INC.; THOMAS, Joshua D.; JONES, Brian D.; KELLEHER, Eugene W.; LOWINGER, Timothy B.; YANG, Liping; YIN, Mao; YURKOVETSKIY, Aleksandr V.; (397 pag.)WO2019/126691; (2019); A1;,
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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. 193290-19-6, name is Methyl 2-(4-bromo-2-fluorophenyl)acetate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Methyl 2-(4-bromo-2-fluorophenyl)acetate

A suspension of methyl (4-bromo-2-fluorophenyl)acetate (5.5 g, 0.0223 mol; see step (v) above), Zn(CN)2 (1.79 g, 0.0156 mol) in dry DMF (30 mL) was purged with argon for 15 minutes before Pd(PPh3)4 (1.27 g, 0.0011 mol) was added. The resulting suspension was stirred at 800C overnight under a nitrogen atmosphere before the reaction was quenched with water and extracted with ethyl acetate. The organic layer was washed with water and brine and dried over sodium sulfate. Solvent evaporation under reduced pressure, followed by purification over silica gel (using 18% ethyl acetate in petroleum ether as eluent) gave the sub-title compound (3.6 g) as a pale yellow solid.

According to the analysis of related databases, 193290-19-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; WO2007/69986; (2007); A1;,
Ester – Wikipedia,
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Reference of 54535-22-7, 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. 54535-22-7, name is Diethyl 2-((phenylamino)methylene)malonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Compound 23 (4.77 g, 47.7 mmol) was added dropwise to Compound 22 (10 g, 46.3 mmol) with subsurface N2 flow to drive out ethanol below 30 C for 0.5 hours. The solution was then heated to 100-110 C and stirred for 2.5 hours. After cooling the mixture to below 60 C, diphenyl ether was added. The resulting solution was added dropwise to diphenyl ether that had been heated to 228-232 C for 1.5 hours with subsurface N2 flow to drive out ethanol. The mixture was stirred at 228-232 C for another 2 hours, cooled to below 100 C and then heptane was added to precipitate the product. The resulting slurry was stirred at 30 C for 0.5 hours. The solids were then filtered, and the cake was washed with heptane and dried in vacuo to give Compound 25 as a brown solid. 1H NMR (DMSO-d6; 400 MHz) delta 12.25 (s), delta 8.49 (d), delta 8.10 (m), delta 7.64 (m), delta 7.55 (m), delta 7.34 (m), delta 4.16 (q), delta 1.23 (t).

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, Diethyl 2-((phenylamino)methylene)malonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; VAN GOOR, Fredrick, F.; WO2013/67410; (2013); A1;,
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