Tag: M.W=200-300

27007-53-0, A common compound: 27007-53-0, name is Methyl 2-bromo-5-chlorobenzoate, 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.

A solution of 2-bromo-5-chloro-benzoic acid methyl ester Compound 4-2 (5.08 g, 20.4 mmol), the boronate Compound 4-1 (6.00 g, 19.4 mmol), PdCl2dppf-CH2Cl2 (1.06 g, 1.30 mmol) and K2CO3 (8.9 g, 58.21 mmol) in DMF and EtOH (4:1, 90 mL) was prepared in a thick walled tube. The mixture was stirred under argon at rt for 5-10 min and the tube was closed and heated at 90 C. for 5 hrs (4-16 hrs for other examples). The mixture was cooled to rt then filtered thru a pad of Celite, washing with EtOAc. The solvent was evaporated and purified by flash chromatography (gradient elution with 5-50% EtOAc in heptane with 0.1% TEA). The desired product Compound 4-3 was isolated as yellow liquid (4.05 g, 60%). 1H NMR (300 MHz, CDCl3) delta 7.82 (d, J=2.2 Hz, 1H), 7.43 (d of d, J=8.2 and 2.2 Hz, 1H), 7.14 (d, J=8.2 Hz, 1H), 5.51 (br s, 1H), 4.02 (br s, 2H), 3.85 (s, 3H), 3.63 (t, J=5.6 Hz, 2H), 2.30 (br s, 2H), 1.50 (s, 9H); MS (ES+) m/z 374.0 (M+Na).

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-bromo-5-chlorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ghosh, Shyamali; Kinney, William A.; Lawson, Edward C.; Luci, Diane K.; Maryanoff, Bruce E.; Sommen, Francois Maria; Pan, Yongchun; US2008/39454; (2008); A1;,
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14062-25-0, 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 14062-25-0 as follows.

Ethyl-2-(4-bromophenyl)-2-diazoacetate (5j). To a solution of ethyl-4-bromophenylacetate (9j) (400 mg, 1.65 mmol) and 4-acetamidobenzenesulfonylazide (p-ABSA) (593 mg, 2.47 mmol) in dry CH3CN (4 mL) at 0C 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (376 mg, 2.47 mmol) was added. The mixture was stirred at it overnight, poured onto water (30 mL) andextracted with EtOAc (3 x 30 mL). The combined organic layers were washed with brine (40 mL), dried over Na2SO4 and the solvent evaporated under reduced pressure. The residue was dissolved in C112C12 (30 mL) whereby the side product 4-acetamidobenzenesulfonamide precipitated as a white solid. The suspension was filtered through silica gel and concentrated to afford an orange solid 5j (359 mg, 81 %).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 14062-25-0, and friends who are interested can also refer to it.

Reference:
Patent; ALLOCYTE PHARMACEUTICALS AG; BREITENSTEIN, Werner; HUERZELER, Marianne; KELLY, Terence; MANCUSO, Riccardo; SCHNEIDER, Gisbert; WEITZ-SCHMIDT, Gabriele; WO2015/189265; (2015); A1;,
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Adding some certain compound to certain chemical reactions, such as: 14062-25-0, name is Ethyl 2-(4-bromophenyl)acetate, 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 14062-25-0. 14062-25-0

(4-bromophenyl)-acetic acid ethyl ester (0.1 g, 0.41 mmol) was dissolved in 1 mLof THF. t-BuOK (0.092 g,0.82 mmol) was added thereto, and iodomethane (0.051 mL, 0.82 mmol) was added thereto at 0C. The mixture wasstirred at room temperature for 18 hours. After addition of 1N HCl and water, the reaction solution was extracted withEtOAc. The organic layer was separated, dried with MgSO4 and purified by column chromatography to obtain the titlecompound (0.047 g, 42%).1H-NMR (CDCl3) delta 7.42 (2H, d), 7.21 (2H, d), 4.11 (2H, q), 1.54 (6H, s), 1.18 (3H, t).

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 Ethyl 2-(4-bromophenyl)acetate.

Reference:
Patent; LG Chem, Ltd.; KIM, Young Kwan; PARK, Sang Yun; JOO, Hyun Woo; CHOI, Eun Sil; PAEK, Seung Yup; KANG, Seung Wan; KIM, Byung Gyu; LEE, Chang Seok; KIM, Sung Wook; LEE, Sang Dae; (369 pag.)EP3239143; (2017); A2;,
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57381-43-8, Adding a certain compound to certain chemical reactions, such as: 57381-43-8, name is Methyl 2,5-dibromobenzoate, 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 57381-43-8.

[150] To a dried 25 mL flask was introduced 3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol- 5-amine (intermediate C, 220 mg, 0.96 MMOL), methyl 2,5-dibromobenzoate (235 mg, 0.80 MMOL), Pd2 (dba) 3 (36.6 mg, 0.04 MMOL), BINAP (49.8 mg, 0.08 MMOL), and CS2CO3 (365 mg, 1.12 MMOL). The flask was degassed followed by addition of toluene (1 mL), and the mixture was then heated to 110¡ãC for 20 h. The mixture was cooled to rt, and diluted with ethyl acetate. The solid was filtered off, and the solvent was removed under reduced pressure. The residue was redissolved in METHANOL/THF (4: 1, V/V) and filtered though a CB-SILICA plug. HPLC purification using a gradient elution from 10percent to 90percent acetonitrile in water afforded 110 MG (31 percent) of the TITLE COMPOUND.APOS;H NMR (300 MHZ, CD2CI2) 5 9.21 (s, 1 H), 7.41 (d, 1 H), 7.20-7. 30 (m, 5 H), 7.10 (d, 1 H), 6.09 (s, 1 H), 3.72 (s, 3 H), 2.04 (s, 3 H), 1.30 (s, 9 H). ES-MS M/Z 444.1 (MH+) ; HPLC RT (min) 4.30.

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 2,5-dibromobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2004/50650; (2004); A1;,
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609-12-1, 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 609-12-1 as follows.

[00281] 3-Methyl-2-(2-methyl-1H-indol-4-yloxy)-butyric acid ethyl ester (2): A mixture of 4-hydroxy-2-methylindole (1) (1.5 g, 0.010 mole), 2-bromo-3-methyl-butyric acid ethyl ester (2.2 g, 0.010 mole) and potassium carbonate (excess) in acetone (50 mL) was refluxed for 3 days. The reaction mixture was filtered, and the filtrate was concentrated. The residue was purified by column chromatography (20:1 Hex:EtOAc) to afford intermediate 2. Yield: 1.88 g, 71 %

According to the analysis of related databases, Ethyl 2-bromo-3-methylbutanoate, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ILYPSA, INC.; WO2007/56280; (2007); A1;,
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59247-47-1, These common heterocyclic compound, 59247-47-1, name is tert-Butyl 4-bromobenzoate, 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 sealed tube was added 5-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-L2-oxazol-4-yl]methoxy ]-3-methyl-2-azabicydo[2.2.l]heptane trifluoroacetic acid salt 360m(250 mg, 0.49 mmol, 1.00 equiv.), tert-buty 4-bromobenzoate (196 mg, 0.76 mmol, 1.5010 equiv.), Ruphos precatalyst (lOS rng, 0.20 equiv ), Ruphos (59.5 mg, 0.20 equiv.), tol (6 mL),and Cs2CCh (595 mg, 1.83 mmol, 3.00 equiv.). The resulting mixture was heated at 110 ¡ãCovernight. After cooling to room temperature, f-hO (l 00 mL) was added, the mixture wasextracted ¡¤with ethyl acetate (lOO mL x 2). The combined organic extracts vvere washed withbrine (200 mL x 2), dried over anhydrous sodium sulfate, and concentrated under vacuum15 The residue was purified by silica gel column chromatography eluting with ethylacetate/petroleum ether (1:3) to give tert-butyl 4-(5-[[5-cydopropyl-3-(2,6-dichloropheny l)-1 ,2-oxazol-4-yl]methoxy]-3-methyl-2-azabicyclo[2.2.l ]hept:m-2-yl)benzoate 360n (230 mg,81 percent) as a light yellow foam

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 59247-47-1.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (582 pag.)WO2018/39386; (2018); A1;,
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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. 3469-00-9 name is Methyl Diphenylacetate, 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. 3469-00-9

2.1 Methyl 2-(cyclohex-2-enyl)-2,2-diphenylacetate (1) Lithium di-isopropylamide (LDA) was generated in situ by slow addition of n-BuLi (1.65 mL, 1.6 mol/L, 2.65 mmol, 1.3 equiv.) to the solution of di-isopropylamine (371 mg, 2.87 mmol, 1.2 equiv.) in THF (4 mL) and stirred for 0.5 h at -78 C. Methyl diphenylacetate (500 mg, 2.21 mmol) in THF (5 mL) was added slowly over 1 h at the same temperature and stirred for an additional 1 h. 3-Bromocyclohexene (391.3 mg, 2.431 mmol, 1.1 equiv.) was added slowly to the reaction mixture, allowed to warm up at room temperature freely and stirred for 24 h. Quenched with aqueous HCl (5 mL, 1 mol/L), stirred and partitioned between H2O (10 mL) and CH2Cl2 (3 *20 mL), the organic layer was combined, dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure and purified by column chromatography with EtOAc/n-hexane (1/20, v/v) afforded 1 as a clear colorless oil (500 mg, 86%) which was crystallized from n-hexane. 1H NMR (400 MHz, CDCl3): delta 7.29-7.26 (m, 10 H, 2Ph-H), 5.67-5.62 (m, 2H, 2′,3′-H), 3.81 (m, 1H, 2-H), 3.62 (s, 3H, Me), 1.88-1.01 (m, 6H, 4′,5′,6′-H).

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

Reference:
Article; Sohail, Muhammad; Wang, Yao-Feng; Wu, Shao-Xiang; Zeng, Wei; Guo, Ji-Yi; Chen, Fu-Xue; Chinese Chemical Letters; vol. 24; 8; (2013); p. 695 – 698;,
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83-27-2, 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. 83-27-2, name is Diethyl 2-(sec-butyl)malonate, This compound has unique chemical properties. The synthetic route is as follows.

STEP A: 1-(3,4-dichlorophenyl)-4-(sec-butyl)-pyrazolidine-3,5-dione 50 g of 3,4-dichlorophenylhydrazine (85%) and 122.5 g of diethyl sec-butyl-malonate were heated for 10 hours at 180 C. (external temperature) while distilling 21.3 g of ethanol. The remainder was taken up in 200 ml of methylene chloride, and the solution was extracted with 2N sodium hydroxide, then with water. The combined aqueous phases were washed with methylene chloride and acidified to pH 1 by concentrated hydrochloric acid. The precipitate was separated, washed with water, separated, dried under reduced pressure at 40 C. to obtain 64.8 g of 1-(3,4-dichlorophenyl)-4-(sec-butyl)-pyrazolidine-3,5-dione melting at 118-120 C.

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; Roussel Uclaf; US4808210; (1989); A;,
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104901-43-1,Some common heterocyclic compound, 104901-43-1, name is Methyl 3-bromo-4-methylbenzoate, 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.

A pressure vessel was charged with methyl 3-bromo-4-methylbenzoate (5.0 g, 22 mmol), DMF (20 ml), water (1.25 ml) and tributylamine (8 ml, 34 mmol). Cesium acetate (2.1 g, 11 mmol) was then added and the flask was purged with N2. Palladium acetate (0.25 g, 1.0 mmol) and triphenylphosphine (2.9 g, 11 mmol) were added and the flask was purged with CO gas. The reaction mixture was then heated at 90 C. under 20 psi of CO gas with vigorous stirring overnight. The reaction mixture was diluted with 50 mL of toluene and extracted with saturated NaHCO3 (3*50 ml). The combined aqueous layer was washed with EtOAc (10 mL), then acidified using 2 N HCl to pH 5. The volume was reduced to about 50 mL and the resulting precipitate was collected by filtration, washed with water and dried to give 5-(methoxycarbonyl)-2-methylbenzoic acid as a white solid. MS (ESI, pos. ion) m/z: 193.1 (M-1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 104901-43-1, its application will become more common.

Reference:
Patent; Dimauro, Erin F.; Bemis, Jean E.; Chaffee, Stuart C.; Chen, Ning; Hu, Essu; Kunz, Roxanne; Martin, Matthew W.; McGowan, David C.; Rumfelt, Shannon; US2007/72862; (2007); A1;,
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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. 252881-74-6, name is tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, A new synthetic method of this compound is introduced below., 252881-74-6

Compound 25 (50 mg, 40 mol), PyAOP (34 mg, 60 mumol) and DIPEA (15.2 muL, 160 mumol) were mixed in 2 mL of dry CH2Cl2 at rt. A portion of 7 (15 mg, 48 mumol) was then added and the resulting yellow solution was stirred for 4 h at rt. The crude reaction was washed with 0.01 N HCl (2¡Á10 mL), dried over Na2SO4, and concentrated. The benzyl-protected product was purified by preparative TLC (10% MeOH/CH2Cl2) and obtained as a white viscous solid (46 mg, 75%). TLC Rf=0.7 (10% MeOH/CH2Cl2). 1H NMR (CDCl3, 500 MHz) delta 1.42 (9H, s), 3.27-3.28 (2H, m), 3.50-3.52 (2H, m), 3.59-3.66 (12H, m), 4.02-4.07 (3H, m), 4.15-4.18 (3H, m), 4.90-4.94 (3H, m), 5.03-5.20 (12H, m), 7.10-7.45 (36H, m), 7.65-7.67 (2H, m), 7.85-7.85 (1H, m), 7.99 (1H, bs), 8.49-8.54 (3H, m) ppm. 13C NMR (CDCl3, 125 MHz) delta 28.3, 39.9, 40.2, 51.3, 51.4, 63.9, 64.1, 69.7, 70.0, 70.2, 70.3, 70.4, 71.1, 71.2, 76.2, 76.3, 79.0, 116.7, 117.5, 120.3, 123.0, 124.2, 125.4, 126.1, 126.2, 127.6, 127.6, 127.8, 128.2, 128.3, 128.4, 128.4, 128.4, 128.5, 128.6, 128.6, 128.7, 128.8, 128.8, 129.0, 130.2, 135.4, 135.7, 135.9, 135.9, 136.1, 146.8, 146.9, 149.0, 151.5, 151.8, 155.9, 164.2, 164.8, 164.9, 165.8, 168.9, 169.0, 169.1 ppm. HRMS (ESI): [M+Na]+ m/z calcd., 1550.5942. found, 1550.5977.

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; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; Nolan, Elizabeth Marie; Zheng, Tengfei; Chairatana, Phoom; US2015/105337; (2015); A1;,
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