Tag: M.W=200-300

Reference of 41841-16-1,Some common heterocyclic compound, 41841-16-1, name is Methyl 2-(4-bromophenyl)acetate, 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.

Methyl 2-(4-bromophenyl)acetate (1.00 g, 4.37 mmol)Dissolved in anhydrous DMF (12.5mL),The reaction solution is under N2 protection,Add NaH (700 mg, 17.5 mmol, 60%) at 0 C.Stir for about 15 minutes,CH3I (1.62 mL) was added slowly.After the dropwise addition was completed, the reaction solution was further stirred at 0 C for 15 minutes.Then transfer to room temperature for 12 h.After the reaction with saturated ammonium chloride (20mL) The reaction was quenched and extracted with EA (20mL), the organic layer was washed with saturated brine (30 mL), thenAfter concentration under reduced pressure,To give the title compound as a yellow oily substance (1.12g, 99.8%).

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-(4-bromophenyl)acetate, its application will become more common.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Liu Xinchang; Ren Qingyun; Yan Guanghua; S ¡¤geerdeman; Zhang Yingjun; (200 pag.)CN109678859; (2019); A;,
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Electric Literature of 346603-63-2, The chemical industry reduces the impact on the environment during synthesis 346603-63-2, name is Methyl 2-methyl-3-(trifluoromethyl)benzoate, I believe this compound will play a more active role in future production and life.

To a solution of 2-methyl-3-trifluoromethyl-benzoic acid methyl ester (0.95 g, 4.35 mmol) in benzene (10 mL) was added N-bromosuccinimide (0.77 g, 4.33 g) and benzoyl peroxide (0.052 g, 0.21 mmol) and the resulting mixture heated to reflux for 4 h, cooled and stirred at room temperature for 48 h. The mixture was filtered, the filter cake washed with diethyl ether and the filtrate washed with a 1 N sodium thiosulfate solution (10 mL), brine and dried over magnesium sulfate. The mixture was filtered and evaporated and the residue purified via automated flash chromatography (Analogix, SF25-80 g column, 5->10% ethyl acetate/hexane gradient) to give 2-bromomethyl-3-trifluoromethyl-benzoic acid methyl ester (1.04 g, 3.50 mmol, 81%) as an off white solid; 1H NMR (300 MHz, DMSO-d6) delta ppm 3.72-4.16 (m, 3H), 5.03 (s, 2H), 7.47-8.32 (m, 3H).

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-methyl-3-(trifluoromethyl)benzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Berthel, Steven Joseph; Kester, Robert Francis; Orzechowski, Lucja; US2012/283271; (2012); 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. 19878-18-3, name is trans-Ethyl 4-(aminomethyl)cyclohexanecarboxylate hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C10H20ClNO2

To a mixture of trans-4-(aminomethyl)cyclohexaneethylcarboxylate hydrochloride (3.00 g, 13.5 mmol) prepared as above and K2CO3 (3.73 g, 27.1 mmol) in CH3CN (100 mL) at 09C was added a solution of bromoacetyl bromide (1.1 mol equiv in 20 mL of CH3CN) slowly over 1 h. After 18 h of stirring at 80 C., the inorganic salts were removed by filtration and the organic phase was evaporated under reduced pressure. The residue was washed with H2O (30 mL¡Á3 times) and dissolved in CH2Cl2. The organic phase was dried over Na2SO4, filtered, and evaporated to give a crude product which was further purified by chromatography on silica [gradient elution CH2Cl2 to 30% ethyl acetate (EA)-CH2Cl2, Rf=0.5 (EA/CH2Cl2=4:6)] to obtain ethyl 4-((2-bromoacetamido)methyl)cyclohexanecarboxylate as a white solid. Yield: 2.49 g (60%). 1H NMR (CDCl3): delta=6.54 (br, 1H, -CONH-), 4.12 (q, 2H, -OCH2CH3), 3.90 (s, 2H, BrCH2CO-), 3.16 (t, 2H, -CONHCH2-), 2.22 (m, 1H, CH3CH2COOCH-, cyclohexyl), 1.80-2.10 (m, 4H, CH2-, cyclohexyl), 1.52 (m, 1H, NHCH2CH-, cyclohexyl), 1.49-1.37 (m, 2H, -CH2-, cyclohexyl), 1.24 (t, 3H, -COOCH2CH3), 1.08-0.92 (m, 2H, -CH2-, cyclohexyl). 13CNMR (CDCl3): delta=175.79 (BrCH2 CONH-), 165.57 (-COOCH2CH3), 60.23 (-COOCH2CH3), 45.96 (-COOCH-, cyclohexyl), 43.17 (-NHCH2CH-), 37.12 (-NHCH2 CH-, cyclohexyl), 29.68 (BrCH2CO-), 29.35 (-CH2-, cyclohexyl), 28.34 (-CH2-, cyclohexyl), 14.22 (-COOCH2 CH3). Anal. Calc. for C12H20BrNO3: C, 47.07; H, 6.58; N, 4.57. Found: C, 47.78; H, 6.85; N, 4.72 (purity>95%). FAB-MS (m/z): Calc. for C12H21BrNO3, 306.07 ([MH]+). Found: 306.20.

According to the analysis of related databases, 19878-18-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KYUNGPOOK NATIONAL UNIVERSITY INDUSTRY-ACADEMIC COOPERATION FOUNDATION; Kim, Tae-Jeong; Chang, Yong Min; Kim, Hee-Kyung; Gu, Sung-Wook; US2013/231475; (2013); A1;,
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Application of 61837-46-5, These common heterocyclic compound, 61837-46-5, name is Methyl 2-bromo-4-methylpentanoate, 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.

Preparation of 2-(4-benzyloxy-2-oxo-2H-pyridin-1-yl)-4-methyl-pentanoic acid methyl ester: A solution of 4-benzyloxy-1H-pyridin-2-one (15 g, 74.6 mmol) in N,N,-dimethylformamide (200 mL) was treated with 2-bromo-4-methyl-pentanoic acid methyl ester (29.2 g, 112 mmol, 80% purity) and potassium carbonate (15.5 g, 112 mmol). The mixture was stirred at 80 C. overnight. At this time, the reaction was allowed to cool to 25 C. and was then concentrated to dryness in vacuo. The residue was washed with ethyl acetate (300 mL) and the remaining solid was removed by filtration. The filtrate was concentrated in vacuo. Flash column chromatography (ethyl acetate:petroleum ether:1:2) afforded 2-(4-benzyloxy-2-oxo-2H-pyridin-1-yl)-4-methyl-pentanoic acid methyl ester (18 g, 73%); 1H NMR (300 MHz, CDCl3): delta 7.41-7.36 (m, 5H), 7.21 (d, 1H, J=7.8 Hz), 6.06-6.00 (m, 2H), 5.7 (dd, 1H, J1=10.5 Hz, J2=5.4 Hz), 4.99 (s, 2H), 3.71 (s, 3H), 1.96-1.86 (m, 2H), 1.49-1.42 (m, 1H), 0.96 (d, 3H, J=6.6 Hz), 0.93 (d, 3H, J=6.9 Hz), LC-MS: 330 [M+1]+, tR=2.71 min.

Statistics shows that Methyl 2-bromo-4-methylpentanoate is playing an increasingly important role. we look forward to future research findings about 61837-46-5.

Reference:
Patent; Haynes, Nancy-Ellen; Scott, Nathan Robert; Tilley, Jefferson Wright; US2011/21570; (2011); A1;,
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Adding a certain compound to certain chemical reactions, such as: 53518-15-3, name is 7-Amino-4-(trifluoromethyl)-2H-chromen-2-one, 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 53518-15-3, SDS of cas: 53518-15-3

A vial was charged with S6 (20 mg, 0.027 mmol), 7-amino-4-(trifluoromethyl)coumarin (19 mg, 0.08 1 mmol, 3 eq.), HATU (31 mg, 0.081 mmol, 3 eq.), Et3N (76 1iL, 0.543 mmol, 20 eq.) and DIvIF (500 jiL). Contents were stirred at room temperature and ambient atmosphere for 24 h, after which the solvent was concentrated to dryness, and the crude product was purified via reverse phase HPLC (10-95% MeCN/H20, linear gradient, with constant 0.1% v/v TFA additive; 23 mm run, 42 mL/min flow, detection at 550 nm) to afford S7 (8 mg, 31%). LRMS (ESI) calcd for C46H40F3N30I2S2 [Mj 948.0, found 948.1

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, 7-Amino-4-(trifluoromethyl)-2H-chromen-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; HOWARD HUGHES MEDICAL INSTITUTE; LAVIS, Luke; JRADI, Fadi, M.; (109 pag.)WO2018/182811; (2018); A1;,
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252881-74-6, name is tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, 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: tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate

Acetylenedicarboxylic acid (0.35 g, 3.09 mmol, 1.0 eq. ) was dissolved in NMP (10 mL) and cooled to 0 , to which compound tert-butyl 3- (2- (2- (2-aminoethoxy) ethoxy) ethoxy) -propanoate (2.06 g, 7.43 mmol, 2.4 eq. ) was added, followed by DMTMM (2.39 g, 8.65 mmol, 2.8 eq. ) in portions. The reaction was stirred at 0 for 6 h and then diluted with ethyl acetate and washed with water and brine. The organic solution was concentrated and triturated with a mixture solvent of ethyl acetate and petroleum ether. The solid was filtered off and the filtrate was concentrated and purified by column chromatography (80-90%EA/PE) to give a light yellow oil (2.26 g, >100%yield) , which was used without further purification. MS ESI m/z [M+H] + 633.30.

The synthetic route of 252881-74-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HANGZHOU DAC BIOTECH CO., LTD; ZHAO, Robert Yongxin; ZHUO, Xiaotao; YANG, Qingliang; ZHAO, Linyao; HUANG, Yuanyuan; YE, Hangbo; YANG, Chengyu; LEI, Jun; GAI, Shun; GUO, Huihui; JIA, Junxiang; BAI, Lu; XIE, Hongsheng; ZHOU, Xiaomai; GUO, Zhixiang; LI, Wenjun; CAO, Mingjun; ZHENG, Jun; YE, Zhichang; YANG, Yanlei; (325 pag.)WO2020/6722; (2020); A1;,
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Adding a certain compound to certain chemical reactions, such as: 150529-73-0, name is Methyl 2-(3-bromophenyl)acetate, 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 150529-73-0, category: esters-buliding-blocks

Tributyltin methoxide (28.3 mL, 98 mmol), preparation 25 (15.0 g, 65 mmol), isopropenyl acetate (10.8 mL, 98 mmol), palladium(II)acetate (750 mg, 3.30 mmol) and tri-ortho-tolylphosphine (2.0 g, 6.5 mmol) were stirred together in toluene (75 mL) at 100 C. under nitrogen for 5 hours. After cooling the reaction was diluted with ethyl acetate (150 mL) and 4M aqueous potassium fluoride solution (90 mL) and stirred for 15 minutes. The mixture was filtered through arbocel and the organic phase separated and reduced in vacuo. The residue was purified by flash column chromatography silica gel eluting with a solvent gradient of diethyl ether:pentane (0:100 to 25:75, by volume) changing to dichloromethane to give the title compound as a pale yellow oil (12.6 g). 1H NMR (400 MHz, CDCl3): delta=7.30 (1H, t), 7.19 (1H, d), 7.13-7.10 (2H, m), 3.69 (5H, s), 3.61 (2H, s), 2.15 (3H, s) ppm. LRMS (electrospray): m/z [M+NH4]+224, [M+Na]+229.

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-(3-bromophenyl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pfizer Inc; US2005/222128; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 53518-15-3, 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. 53518-15-3, name is 7-Amino-4-(trifluoromethyl)-2H-chromen-2-one, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 159 8-Hydroxy-N-[4-(trifluoromethyl)coumarin-7-yl]-7-quinolinecarboxamide monohydrochloride (V-11) (Refer to Chart V): According to GP II, starting from anhydride U-1 (200 mg), pyridinium chloride (42 mg), 7-amino-4-(trifluoromethyl)coumarin (85 mg) and CHCl3 (8 mL), amide V-11 is obtained as a yellow powder (25 mg). Physical characteristics are as follows: 1H-NMR (d6-DMSO, 300 MHz) delta 8.94, 8.65, 8.11, 8.05, 7.83, 7.71, 7.66, 7.38, 6.91. 13C-NMR (d6-DMSO, 75 MHz) delta 166.40, 159.13, 155.28, 146.35, 143.73, 140.72, 131.77, 128.52, 125.91, 124.11, 117.29, 116.40, 114.67, 114.57, 108.91, 107.41. MS (EI) m/z 400 (M+), 172, 116, 89.

The chemical industry reduces the impact on the environment during synthesis 7-Amino-4-(trifluoromethyl)-2H-chromen-2-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Pharmacia & Upjohn Company; US6211376; (2001); B1;,
Ester – Wikipedia,
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Reference of 55666-43-8, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 55666-43-8 as follows.

Preparation 12; 1,1-Dimethylethyl 3-[7-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1,3,4,5-tetrahydro-2H-2-benzazepin-2-yl]propan-oate 2-[(1-Methylethyl)oxy]-5-[3-(2,3,4,5-tetrahydro-1H-2-benzazepin-7-yl)-1,2,4-oxadiazol-5-yl]benzonitrile hydrochloride (Example 3) (70 mg, 0.170 mmol) and caesium carbonate (167 mg, 0.511 mmol) were stirred in dry DMF (5 ml) and treated with 1,1-dimethylethyl 3-bromopropanoate (0.043 ml, 0.256 mmol) then stirred at 60 C. for 2 hours. Further quantities of 1,1-dimethylethyl 3-bromopropanoate (44 mul) were added and the reaction stirred at 60 C. for 3 hours. The reaction was left standing overnight. 1,1-Dimethylethyl 3-bromopropanoate (43 mul) was added and the reaction mixture stirred at 60 C. for 7 hours then left standing overnight. EtOAc (50 ml) was added and the reaction mixture washed with water (2¡Á50 ml), dried over anhydrous MgSO4 and evaporated to yield a clear, colourless oil (100 mg). The oil slowly solidified. Trituration with ether/hexane to yielded the title compound (70 mg) as a white solid. MS (ES) C29H34N4O4 requires 502. found 503.0 (M+H).

According to the analysis of related databases, 55666-43-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; US2010/174065; (2010); A1;,
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Some common heterocyclic compound, 176694-36-3, name is Methyl 4-fluoro-3-(trifluoromethyl)benzoate, molecular formula is C9H6F4O2, 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. HPLC of Formula: C9H6F4O2

3-Fluoroazetidine hydrochloride (1 10 mg, 0.99 mmol), /V,/V-diisopropylethylamine (0.34 ml_, 1.98 mmol) and methyl 4-fluoro-3-(trifluoromethyl)benzoate (200 mg, 0.90 mmol) were heated to 65 C in dimethyl sulfoxide (1 ml.) for 4 hours, by which time the starting material appeared to have been consumed by TLC. STEP 2: The reaction mixture was then concentrated under reduced pressure and the crude residue was dissolved in toluene (1 ml.) and ethanol (1 ml_). Hydrazine monohydrate (0.17 ml_, 3.60 mmol) was then added and the reaction mixture was heated at 65 C for 16 hours, by which time the starting material appeared to have been consumed by TLC. The reaction mixture was then concentrated under reduced pressure and the crude residue was recrystallised from cyclohexane and diethyl ether to give crude 4-(3- fluoroazetidin-1 -yl)-3-(trifluoromethyl)benzohydrazide (82 mg, 0.30 mmol, 33% yield) as a yellow solid that was used without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 176694-36-3, its application will become more common.

Reference:
Patent; UCL BUSINESS LTD; FISH, Paul, Vincent; MAHY, William; WILLIS, Nicky, John; WOODWARD, Hannah; ATKINSON, Benjamin, N; BAYLE, Elliott, D; SIPTHORP, James; JONES, Edith, Yvonne; ZHAO, Yuguang; VECCHIA, Luca; RUZA, Reinis, Reinholds; (208 pag.)WO2020/43866; (2020); A1;,
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