Tag: M.W=200-300

These common heterocyclic compound, 55954-25-1, name is Methyl 2-(2,4-Dimethoxyphenyl)acetate, 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. Product Details of 55954-25-1

This compound was prepared from compound 8 in three steps without purifying the intermediate acid and acid chloride. n-BuLi (2.5 M in THF, 0.87 mL, 2.18 mmol) was added drop wise to a stirred solution of 8 (420 mg, 1.82 mmol) in THF (10 mL) at -78 C under N2 atmosphere. After 30 min CO2 gas was passed through the solution during 45 min of time and the mixture was allowed to warm up to room temperature. THF was removed in vacuum and the mixture was treated with saturated NaHCO3 solution (30 mL). The water layer was washed with ethyl acetate (2*15 mL) and then acidified with conc. HCl. The mixture was extracted with ethyl acetate (2*50 mL). The organic layer was washed with water (2*20 mL), brine (20 mL), dried (Na2SO4), filtered and concentrated to get the acid 10 (320 mg). Without further purification it was dissolved in CH2Cl2 (10 mL) under N2 atmosphere, DMF (one drop) and oxalyl chloride (0.23 mL, 2.6 mmol) were added. The mixture was stirred for 3 h at room temperature and then the solvent was removed in vacuum to yield the corresponding acid chloride, which was again directly used for the next reaction without further purification. A solution of compound 1114 (514 mg, 2.45 mmol) in THF (7 mL) was added at -78 C to a freshly prepared solution of LDA, prepared from n-BuLi (2.5 M in THF, 1.3 mL, 3.26 mmol) and i-Pr2NH (0.45 mL, 3.26 mmol) in THF (5 mL) at 0 C under N2 atmosphere. The thus produced yellowish anion was stirred at -78 C for 45 min and then a solution of crude acid chloride, prepared earlier, in THF (10 mL) was added drop wise. The reaction was stirred at the same temperature for another 45 min and then at room temperature for 4 h. 10% HCl (10 mL) was added to quench the reaction, THF was removed in vacuum and the water layer was extracted with ethyl acetate (2*50 mL). The organic layer was washed with water (2*20 mL), brine (20 mL), dried (Na2SO4) and concentrated. The crude product was purified by silica gel column chromatography to get 13 (480 mg, 68% in three steps) as yellowish oily compound. Rf 0.5 (1:1 ethyl acetate:hexane); numax (CHCl3) cm-1 1732, 1659, 1608, 1508, 1463, 1211, 1029; 1H NMR (CDCl3, 500MHz): delta 7.71 (s, 1H, C6?-H), 7.01 (d, 1H, J=8.5Hz, C6?-H), 6.43 (s, 1H, C3?-H), 6.41 (d, 1H, J=8.5Hz, C5?-H), 6.28 (s, 1H, C3?-H), 5.94 (s, 1H, C2-H), 3.82 (s, 3H, OCH3), 3.76 (s, 3H, OCH3), 3.75 (s, 3H, OCH3), 3.74 (s, 3H, OCH3), 3.71 (s, 3H, CO2CH3), 2.10 (s, 3H, CH3); 13C NMR (CDCl3, 125MHz): delta 193.1 (C), 171.1 (C), 163.0 (C), 160.3 (C), 159.6 (C), 157.9 (C), 133.1 (CH), 130.1 (CH), 118.9 (C), 118.0 (C), 115.8 (C), 104.1 (CH), 98.4 (CH), 94.1 (CH), 57.2 (CH3), 55.5 (CH3), 55.3 (CH3), 55.2 (CH3), 55.2 (CH3), 52.1 (CH), 15.3 (CH3); HRMS (EI+) m/z 388.1529 ([M]+ C21H24O7, requires 388.1521).

The synthetic route of Methyl 2-(2,4-Dimethoxyphenyl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pahari, Pallab; Saikia, Ujwal Pratim; Das, Trinath Prasad; Damodaran, Chendil; Rohr, Juergen; Tetrahedron; vol. 72; 23; (2016); p. 3324 – 3334;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 609-12-1, 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. 609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, This compound has unique chemical properties. The synthetic route is as follows.

[00485] 2-(1’Benzyl’2-methyl-1H-indol-4’yloxy)-3-methyl-butyric acid ethyl ester 7:1-Benzyl-2-methyl-1H-indol-4-ol 3 (0.3 g 1.26 mmole) was dissolved in anhydrous dimethylformamide (20 ml_). To the solution sodium hydride 60% in mineral oil (66 mg 1.65 mmole) was added. The mixture was stirred at room temperature for 1 h. To the mixture ethyl-2-bromoisovalerate (0.344 mL, 1.65 mmole) was added. The mixture was stirred at room temperature for 18 h. The reaction was diluted with ethyl acetate (300 mL) and washed with H2O (4 x 100 mL) and brine (1 x 100 mL). The organic layer was separated, dried with magnesium sulfate and concentrated. The residue was purified by column chromatography (10:1 Hexane:EtOAc) to afford a 1 :1 mixture of 7:ethyl-2-bromoisovalerate. Further purification by column chromatography (10:1 Hexane.epsilontOAc) afforded 7 (0.09 g, 19 %) as a yellow oil.

The chemical industry reduces the impact on the environment during synthesis Ethyl 2-bromo-3-methylbutanoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ILYPSA, INC.; WO2007/56279; (2007); A2;,
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. 849758-12-9, name is Methyl 4-bromo-3-fluorobenzoate, A new synthetic method of this compound is introduced below., Quality Control of Methyl 4-bromo-3-fluorobenzoate

a- Synthesis of Int. 272: In a microwave vial, a mixture of methyl 4-bromo-3-fluorobenzoate (1.00 g 4.3 mmol), cyclopropylboronic acid (1.1 g, 13 mmol) and KF (0.75 g, 13 mmol) in dry toluene (10 mL) was purged with N2. Pd(PPh3)4 (0.25 g, 0.22 mmol) was added and the mixture was purged again with N2 and heated at 150C for 2h. The crude was partitioned between DCM and water. The organic layer was separated, dried over MgS04, filtered through a pad of silica gel and evaporated in vacuo to give 0.85 g of Int. 272 (quant.) which was used as such in the next reaction step.

The synthetic route of 849758-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; MEVELLEC, Laurence, Anne; PASQUIER, Elisabeth, Therese, Jeanne; DESCAMPS, Sophie; MERCEY, Guillaume, Jean, Maurice; WROBLOWSKI, Berthold; VIALARD, Jorge, Eduardo; MEERPOEL, Lieven; JEANTY, Matthieu, Ludovic; JOUSSEAUME, Thierry, Francois, Alain, Jean; WO2015/144799; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 82702-31-6, name is Methyl 3-bromo-4-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., name: Methyl 3-bromo-4-fluorobenzoate

Sodium hydride (0.88 g, 22 mmol, 60% w/w) was added to N,N (1r,4r)-4-methylcyclohexane-1-ol (0.84 g, 7.3 mmol) at 0 C – in dimethylformamide (30 mL) solution. The reaction solution was stirred at 0 C for 10 minutes. Then, methyl 3-bromo-4-fluorobenzoate (1.8 g, 8.2 mmol) was added, and the mixture was stirred at room temperature for 10 hours. The reaction was quenched with saturated ammonium chloride, ethyl acetate (50mL * 2), washed with saturated brine (20mL * 5) The organic phase was dried and evaporated to dryness to give a crude product. The crude product was subjected to column separation (petroleum ether: ethyl acetate = 20:1) to give a methyl group. 3-Bromo-4-(((1r,4r)-4-methylcyclohexyl)oxo)benzoate (1.2 g, yield 50%).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 82702-31-6.

Reference:
Patent; Shanghai Hansen Bio-pharmaceutical Technology Co., Ltd.; Jiangsu Haosen Pharmaceutical Group Co., Ltd.; Ye Guozhong; Liu Lei; Bao Rudi; Wu Shenghua; Deng Haining; (130 pag.)CN110041253; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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, Product Details of 150529-73-0

(The following reaction is done in an oxygenfree N2 atmosphere.) Add ethanol (0.8mL), Tetrakis-(triphenylphosphine)-palladium(0) (30mg, 2.2mol%) and Na2CO3 decahydrate (944mg, 3.30mmol; presolved in 1.2mL H2O) subsequently to dissolved 2-Amino-benzeneboronic acid (48) (201mg, 1.30 mmol) in toluene (6.0mL). Degas the reaction mixture for 5 times and flood with N2 again. Add (3-Bromo-phenyl)-acetic acid methyl ester (47) (270mg, 1.18mmol) in toluene (6.0 mL), degas again (5 times) and stir the reaction solution overnight at 100C. Partition the reaction solution between EtOAc and brine (1+1) and extract the separated aqueous layer 3 times with EtOAc. Wash combined organic layer with brine and dry with Na2SO4. Remove solvent under reduced pressure and purify the crude product by preparative radial chromatography (silica gel 60PF, CyH/EtOAc 3+1) to obtain (2′-Amino-biphenyl-3-yl)-acetic acid methyl ester (49) as an orange oil (304mg, 81%). 1H NMR (400MHz, CDCl3): 3.66 (s, 2 H); 3.69 (s, 3 H); 3.62-3.86 (br.s, 2 H); 6.75 (d, 1 H, J= 8.1Hz); 6.80 (t, 1 H, J= 7.3Hz); 7.11 (d, 1 H, J= 7.3Hz); 7.15 (d, 1 H, J = 8.1Hz); 7.22-7.26 (br.m, 1 H); 7.32-7.42 (m, 3 H).

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

Reference:
Patent; Revotar Biopharmaceuticals AG; EP1764093; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 35450-37-4, 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. 35450-37-4, name is Methyl 3-bromo-4-methoxybenzoate, This compound has unique chemical properties. The synthetic route is as follows.

Step 1 To a 250 mL RBF was added methyl 3-bromo-4-methoxybenzoate (4.0 g, 16.3 mmol). The flask was flushed with N2. THF (60 mL) was added, followed by allylmagnesium bromide (39.2 mL, 39.2 mmol, 1.0 M in ether) at 0 C. via a syringe over 10 mins. The resulting reaction mixture was stirred at 0 C. for 2 hrs. It was quenched by addition of 50 mL sat. NH4Cl at 0 C. and 100 mL of water. The product was extracted with EtOAc (3*100 mL). Organics were washed with 100 mL brine, dried over sodium sulfate, filtered, and concentrated to give 4-(3-bromo-4-methoxyphenyl)hepta-1,6-dien-4-ol (5.0 g) as a colorless oil. 1H NMR (500 MHz, CDCl3:) delta 7.61 (s, 1H), 7.30 (d, 1H), 6.88 (d, 1H), 5.63 (m, 2H), 5.12 (d, 4H), 3.93 (s, 3H), 2.65 (m, 2H), 2.53 (m, 2H).

The chemical industry reduces the impact on the environment during synthesis Methyl 3-bromo-4-methoxybenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Shao, Pengcheng Patrick; Sun, Wanying; Katipally, Revathi Reddy; Vachal, Petr; Ye, Feng; Liu, Jian; Sha, Deyou; US2013/109649; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 106896-49-5, The chemical industry reduces the impact on the environment during synthesis 106896-49-5, name is Methyl 4-amino-3-bromobenzoate, I believe this compound will play a more active role in future production and life.

To a 1L rmmd-boitom t1ask purged with and rnaintained under an inert atrnosphere of.5 nitrogen vvas added methyl 4-amino-3-bromobenzoate 249a (13.6 g, 59.12 mmol, 1.00equiv.), (furan-3-yl)boronic acid (10 g, 89.37 mmol, 1.50 equiv.), 1,4-dioxane (500 mL), 1Maq. NaHC01 (17.5 g, 3.50 equiv.), and tetrakis(triphenylphosphine) palladium (6.86 g, 5.94mmol, 0.10 equiv.). The resulting mixture was heated at ll (J”C overnight vvith stirring. Aftercooling to room temperature, the mixture was diluted with 200 mL of water, and extracted10 with ethy 1 acetate (500 mL x 2). The combined orga.nic extracts were washed successivelywith t-hO (500 mL) and brine (500 mL x 2), dried over anhydrous sodium sulfate, andconcentrated under vacuum The crude product was purified by Flash-Prep-HPLC using thefollowing conditions (lntelFlash-1 ): Colunm, silica gel; mobile phase: EA: PE=O: 100increasing toEA: PE'”50:50 within 20 min; Detector, UV 254 nm. Removal of sol vents gavel 5 methyl 4-amino-3-(furan-3-yl)benzoate 25 l a (8.345 g, 65%) as a yellow oil.

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 4-amino-3-bromobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (582 pag.)WO2018/39386; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 55666-43-8, name is tert-Butyl 3-bromopropanoate, 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 55666-43-8, Recommanded Product: tert-Butyl 3-bromopropanoate

Cyclohexanecarboxylic acid (2.89 g, 22.6 mmol) was dissolved in THF (30 mL) and this solution added to a lithium diisopropylamide solution cooled to -15 C. (2M in THF/n-heptane/ethylbenzene, Aldrich) 24.3 mL (48.6 mmol) at such a rate as to keep the temperature below 0 C. The reaction mixture was then stirred at 0 C. for 2.5 hours before re-cooling to -15 C. and the addition of tert-butyl 3-bromopropionate (5 g, 23.9 mmol) in THF (50 mL) at such a rate as to keep the temperature below 0 C. The reaction mixture was allowed to reach room temperature and stirred overnight, before the reaction mixture was quenched by the addition of 2M HCl and extracted with ethyl. acetate 2×200 mL. The combined organic layers were dried (MgSO4) and then evaporated to an orange oil. Purification by flash chromatography [SiO2; dichloromethane/methanol/0.880 NH3 (97:3:0.5)] afforded the title compound as a gummy oil (800 mg, 14%). 1H NMR (CDCl3, 400 MHz), deltaH: 2.22 (2H, m), 2.07-2.00 (2H, m), 1.86 (2H, m), 1.45-1.16 (8H,m), 1.41 (9H, s): m/z (ES+) 279(MNa+); m/z (ES-) 255 M-H+)

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, tert-Butyl 3-bromopropanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pfizer Inc; US2004/180941; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 88709-17-5 as follows. Recommanded Product: Ethyl 2-ethoxy-4-methylbenzoate

00465] Step 2: Synthesis of ethyl 4-(bromomethyl)-2-ethoxybenzoate: To a solution of ethyl 2-ethoxy-4-methylbenzoate (100 mg, 0.481 mmol) in 2 mL oftrifluoromethyl toluene was added NBS (94 mg, 0.529 mmol) and AIBN (10 mg) in portions. The mixture was heated to reflux and stirred for 24 h. The reaction mixture was concentrated, diluted with 10 mL of EA, washed with 5 mL of 4 N NaOH, 5 mL of brine, dried over anhydrous Na2S04 and concentrated under reduced pressure to afford ethyl 4-(bromomethyl)- 2-ethoxybenzoate as brown oil (42 mg, 30%), which was used for the next step directly.

According to the analysis of related databases, 88709-17-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; N30 PHARMACEUTICALS, LLC; SUN, Xicheng; QIU, Jian; WO2011/38204; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 773134-11-5, These common heterocyclic compound, 773134-11-5, name is Methyl 4-bromo-2,6-difluorobenzoate, 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 25 mL round-bottom flask was added methyl4-bromo-2,6-difluorobenzoate104h (160 mg, 0.64 mmol, 1.2 equiv.), (1S,4S,5R)-5-[5-cydopropyl-3-(2,6-dichlorophenyl)L2-oxazol-4-yl]methoxy-2-azabicyclo[2.2.1]heptane 12dd (200 mg, 0.394 mmol, 1.0 equiv.),25 Pd(OAc)2 (60 mg, 0.27 mmoL 0.69 equiv.), Xantphos (150 mg, 0.26 mmol, 0.66 equiv.),Cs2C01 (340 mg, 1.04 mmol, 2.64 equiv.), and toluene (4 mL). The resulting mixture was stirred at 90C overnight. Upon cooling, the mixture v.·as diluted vvith 20 mL ofi-bO andextracted with ethyl acetate (20 mL x 2). The combined organic extracts vvere washed withVater (20 mL x 2), dried over anhydrous sodium sulfate and concentrated under vacuum. Theresidue was purified by silica gel colunm chromatography eluting with ethyl5 acetate/petroleum ether (1 :5) to give 4-[(lS,4S,5R)-5-[[5-cyclopropy-3-(2,6-dichlorophenyl)-1 ,2-oxazol-4-yl]methoxy ]-2-azabicyclo[2.2.1 ]heptan-2-yl]-2,6-difluorobenzoate l04c (26 mg, 12.31()) as a yellow oil.

The synthetic route of 773134-11-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (582 pag.)WO2018/39386; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics