Tag: M.W=200-300

Related Products of 773873-95-3,Some common heterocyclic compound, 773873-95-3, name is Methyl 2,2-difluorobenzo[d][1,3]dioxole-5-carboxylate, molecular formula is C9H6F2O4, 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 stirred solution of methyl 2,2-difluorobenzo[d][1,3]dioxole-5-carboxylate (1.0 g, 4.63 mmol) in MeOH (20 mL) at 0 C was added hydrazine hydrate solution (0.277 mL, 6.94 mmol). The reaction mixture was stirred at RT for 18 hrs. LC-MS showed product and some starting material. Thus , more hydrazine hydrate solution (0.1 mL) was added and the mixture was stirred at RT. After 2 days, LC-MS showed that starting material was still present. More hydrazine hydrate solution (0.277 mL, 6.94 mmol) was added, and the reaction mixture was stirred for 3 days. LC-MS then showed that the reaction was complete. The reaction mixture was concentrated. The initial product was washed with water, filtered and dried under vacuo to give 2,2-difluorobenzo[d][1,3]dioxole-5- carbohydrazide (1.0 g, 4.63 mmol, 100 % yield). 1H NMR (500 MHz, CDCl3) delta 7.50 – 7.60 (m, 2 H), 7.13 (d, J=8.07 Hz, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2,2-difluorobenzo[d][1,3]dioxole-5-carboxylate, its application will become more common.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Yinhong; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; HARVEY, James S.; HEATH, Julie Anne; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; PATTAROPONG, Vatee; SWAMINATH, Gayathri; YEH, Wen-Chen; KREIMAN, Charles; (308 pag.)WO2018/93579; (2018); A1;,
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Reference of 39149-80-9, These common heterocyclic compound, 39149-80-9, name is tert-Butyl 2-bromopropanoate, 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.

[0151] To a solution of 3-chloro-4-methylaniline (400 mg, 2.83 mmol) in acetone (35 mL) was added tert-butyl 2-bromopropanoate (890 mg, 4.26 mmol), KI (940 mg, 5.66 mmol), and K2CO3 (781 mg, 5.66 mmol). The mixture was heated at 60C under N2 then filtrated and concentrated. The residue was purified using silica gel eluting with PE/EA (2: 1) to give tert-butyl 2-((3-chloro-4-methylphenyl)amino)propanoate (151 mg, 19% yield).

The synthetic route of 39149-80-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOTHERYX, INC.; CHAN, Kyle W.H.; CHOURASIA, Aparajita Hoskote; ERDMAN, Paul E.; FUNG, Leah; MERCURIO, Frank; SULLIVAN, Robert; (86 pag.)WO2019/241274; (2019); A1;,
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Related Products of 618-89-3,Some common heterocyclic compound, 618-89-3, name is Methyl 3-bromobenzoate, molecular formula is C8H7BrO2, 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.

2- (3-Bromo-phenyl)-propan-2-ol :; The 3-bromo-benzoic acid methyl ester (1.0 g, 4.7 mmol) in tetrahydrofuran (10 mL) was brought to-78 C followed by the addition of methyl magnesium bromide (7.7 mL, 10.81 mmol) and warmed to room temperature and stirred for 17 h. The mixture was poured into sat NH4Cl and extracted with ethylacetate. The organic extracts were combined, washed with brine, dried over magnesium sulfate and chromatographed on silica gel using 04% methanol/dichloromethane to afford colorless oil.

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

Reference:
Patent; AMGEN INC.; WO2005/70932; (2005); A2;,
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Electric Literature of 792-74-5, These common heterocyclic compound, 792-74-5, name is Dimethyl [1,1′-biphenyl]-4,4′-dicarboxylate, 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.

Example 2 [[1,1′-trans, trans-Bicyclohexyl]-4,4′-diylbis[4,2-oxazoldiyl(2S)-2,1-pyrrolidinyl[(1S)-1-(1-methylethyl)-2-oxo-2,1-ethanediyl]]]bis-carbamic acid dimethyl ester 20 4,4′-Dimethyl biphenyl-4,4′-dicarboxylate 20.1 (9 g, 33 mmol) was hydrogenated in AcOH (100 ml) in the presence of 10percent Pd/C (3 g) and Rh2O3 (0.15 g) at 250° C. for 16 h and pressure of 60-20 atm H2. After that the mixture was filtered off, evaporated at reduced pressure, excess of 10percent K2CO3 solution in water was added and the mixture was extracted with CHCl3. Organic layer was evaporated, it gave 9 g (96percent) of compound 20.2. 1H NMR (CDCl3): 3.67 (s); 3.65 (s) (total 6H, 2Me) 2.56 (1H, br.s) 2.20 (br.t., 1H) 2.0 (m, 4H) 1.80 (br.t, 2H) 1.5-1.0 (m, 12H).

Statistics shows that Dimethyl [1,1′-biphenyl]-4,4′-dicarboxylate is playing an increasingly important role. we look forward to future research findings about 792-74-5.

Reference:
Patent; Alla Chem LLC; Ivachtchenko, Alexandre Vasilievich; Bichko, Vadim Vasilievich; Mitkin, Oleg Dmitrievich; US2013/253008; (2013); A1;,
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Related Products of 24398-88-7, These common heterocyclic compound, 24398-88-7, name is Ethyl 3-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.

The 3-morpholinobenzoyl chloride used as a starting material was prepared as follows: A mixture of ethyl 3-bromobenzoate (1.92 ml), morpholine (1.25 ml), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.336 g), sodium tert-butoxide (1.615 g) and tris(dibenzylideneacetone)dipalladium(0) (0.33 g) and toluene (25 ml) was stirred and heated to 90 C. for 18 hours under argon. The reaction mixture was allowed to cool to ambient temperature and extracted with 1N aqueous hydrochloric acid. The aqueous phase was basified with concentrated sodium hydroxide solution and extracted with ethyl acetate. The organic phase was dried (MgSO4) and evaporated. The residual oil was purified by column chromatography on silica gel using a 47:3 mixture of methylene chloride and methanol as eluent. There was thus obtained N-(3-morpholinobenzoyl)morpholine (0.45 g).

Statistics shows that Ethyl 3-bromobenzoate is playing an increasingly important role. we look forward to future research findings about 24398-88-7.

Reference:
Patent; AstraZeneca AB; US6579872; (2003); B1;; ; Patent; Zeneca Limited; US6498274; (2002); B1;,
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Synthetic Route of 24398-88-7, The chemical industry reduces the impact on the environment during synthesis 24398-88-7, name is Ethyl 3-bromobenzoate, I believe this compound will play a more active role in future production and life.

ethyl-4′-methoxy-biphenyl-3-carboxylate (3b) Preparation according to AV1. To the solution of ZnBr2 (0.67 mL, 1.5 M in THF) and NEP (0.17 mL), 4-methoxyphenyl magnesium bromide (1.57 mL, 0.83 M in THF) was added dropwise and then the catalyst solution (0.08 mL) and ethyl-3-bromobenzoate (229 mg, 1.00 mmol) was added. This solution was stirred for 1 hour at room temperature. The conventional reprocessing and purification by column chromatography (pentane/ether 9:1) yielded 3b as a colourless oil (234 mg, 91%).1H NMR (CDCl3, 300 MHz, 25 C.): delta=8.26 (s, 1H), 8.00-7.97 (m, 1H), 7.73-7.70 (m, 1H), 7.56 (d, J=8.8 Hz, 2H), 7.46 (t, J=7.7 Hz, 1H), 6.99 (d, J=8.7 Hz, 2H), 4.41 (q, J=7.1 Hz, 2H), 3.83 (s, 3H), 1.41 (t, J=7.1 Hz, 3H).13C NMR (CDCl3, 75 MHz, 25 C.): delta=166.5, 159.4, 140.9, 132.5, 130.9, 130.8, 128.6, 128.1, 127.6, 127.1, 114.2, 60.9, 55.2, 14.2.IR (KBr): 2981 (w), 1717 (vs), 1610 (m), 1518 (s), 1439 (m), 1367 (w), 1300 (s), 1249 (vs), 1182 (m), 1109 (s), 1049 (m), 1030 (m), 834 (m), 758 (s), 574 (w).MS (70 eV, EI), m/z (%): 256 (100, M+), 241 (9), 228 (11), 211 (20), 183 (10), 168 (6), 139 (12), 105 (3).HRMS m/z: calculated for C16H16O3: 256.1099; found: 256.1097.

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

Reference:
Patent; knochel, Paul; Gavriushin, Andrei; Kofink, Christiane Charlotte; Manolikakes, Georg; US2010/184977; (2010); A1;,
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51760-21-5, name is Dimethyl 5-bromoisophthalate, 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. Formula: C10H9BrO4

Sodium hydroxide (0.29 g, 7.32 mmol) was added to a suspension of dimethyl 5-bromoisophthalate (2 g, 7.32 mmol) in acetone (30 ml) and water (15 ml) and the reactionstirred at room temperature for 1 hour. A clear solution was achieved at this point. The reaction was stirred overnight at room temperature. The acetone was removed in vacuu and the residual solution extracted with ethyl acetate. The aqueous was then adjusted to pH4 and extracted twice with ethyl acetate. The organic was then washed with brine, dried andconcentrated to give the title compound as a 60 % pure white solid (1.23 g, 2.85 mmol, 38.9% yield). MS (m/z) 259.0/260.9 (bromine isotopes).

The synthetic route of 51760-21-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; DOWDELL, Sarah E.; EIDAM, Hilary Schenck; ELBAN, Mark; FOX, Ryan Michael; HILFIKER, Mark A.; HOANG, Tram H.; KALLANDER, Lara S.; LAWHORN, Brian Griffin; MANNS, Sharada; PHILP, Joanne; WASHBURN, David G.; YE, Guosen; (274 pag.)WO2017/6295; (2017); A1;,
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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 653-92-9 as follows. Safety of Methyl 2-bromo-4-fluorobenzoate

To a solution of 5a (2.00 g, 8.58 mmol), Palladium acetate (0.008 g, 0.04 mmol), PPh3 (0.47 g, 1.69 mmol) and p-tolylboronic acid (10 mL) was added 6 mL of 2 M K2CO3. The mixture was refluxed under nitrogen for 5 h, then diluted with ethyl acetate, and washed with water (50 mL * 3) and brine (50 mL * 3).The organic layer was dried over MgSO4. The solvent was removed under reduced pressure.The residue was purified by flash column chromatography with petroleum ether-ethyl acetate (100/1) as eluant. The product was obtained as a yellow oil. Yield: 82.6%. 1H NMR (CDCl3, 400 MHz) delta: 7.53(1H, dd, J1 = 8.4 Hz, J2 = 2.8 Hz, Ph-H), 7.35(1H,dd, J1 = 8.4 Hz, J2 = 5.6 Hz, Ph-H), 7.25-7.16(5H, m, Ph-H), 3.69(3H, s, Ph-COOCH3)2.41(3H, s, Ph-CH3). ESI-MS (m/z): 245.2 [M+1]+.

According to the analysis of related databases, 653-92-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Da, Ya-Jing; Yuan, Wei-Dong; Xin, Ting; Nie, Yong-Yan; Ye, Ying; Yan, Yi-Jia; Liang, Li-Sha; Chen, Zhi-Long; Bioorganic and Medicinal Chemistry; vol. 20; 24; (2012); p. 7101 – 7111;,
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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 107947-17-1 as follows. Recommanded Product: 107947-17-1

To a solution of commercially available methyl 3-bromo-4-chlorobenzoate (5.00 g, 20.0 mmol) dissolved in MeOH (100 ml.) at 20-25C was added Eta2NuNuEta220 (3.07 g, 61.3 mmol) and the mixture was heated at reflux temperature over night. After that time, the resulting mixture was concentrated under reduced pressure, the residue was suspended in MTBE, the solid contents collected via filtration and dried in a vacuum oven to afford the title compound (4.34 g, 87%). (0560) LC-MS: Mass calculated for C7H7BrCIN20+ [(M+H)+)] 248.9, found 248.9; RT = 0.756 min.

According to the analysis of related databases, 107947-17-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BASF SE; GOCKEL, Birgit; HUWYLER, Nikolas; KOERBER, Karsten; NARINE, Arun; MCLAUGHLIN, Martin John; (82 pag.)WO2018/224455; (2018); A1;,
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Reference of 206551-41-9, 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. 206551-41-9 name is Methyl 3-bromo-2-fluorobenzoate, 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.

Step 1: Methyl 3-((2-chloro-5-(1 ,4-dimethyl- 1H-1 ,2,3-triazol-5-yl)pyridin-3- yl)amino)-2-fluorobenzoateTo a 70 mL pressure vial containing 2-chloro-5-(1,4-dimethyl-1H-1,2,3-triazol-5- yl)pyridin-3-amine (Step 1 of Example 54, 500 mg, 2.24 mmol), methyl 3-bromo-2-fluorobenzoate (Oakwood, 781 mg, 3.35 mmol) and Cs2CO3 (728 mg, 2.24 mmol) in dioxane (10 mL) was added 1,1 ?-bis(diphenylphosphino)ferrocene (62.0 mg, 0.11 mmol), Pd(OAc)2 (85 mg, 0.38 mmol) and Xantphos (65 mg, 0.11 mmol). N2 was bubbled through the reaction mixture for 2 mm. The vial was sealed and heated to 100 °C for 24h. BrettPhos precatalyst (100 mg, 0.12 mmol) and additional methyl 3-bromo-2-fluorobenzoate (781 mg, 3.35 mmol) were added. N2 was bubbled through the reactionmixture for 2 mm, and then heating was continued at 110 °C for 24 h. Additional BrettPhos precatalyst (100 mg, 012 mmol) was added and stirring was continued at 120°C for 5 h. BrettPhos precatalyst (100 mg, 0.12 mmol) was again added and the reaction mixture was heated at 120 °C for 5 h. After cooling to room temperature, the mixturewas diluted with CHC13 and filtered through Celite® rinsing with CHC13. The filtrate was concentrated and purified using ISCO silica gel chromatography (40 g column, gradient from 0percent to 100percent EtOAc/CH2C12) to give the title compound (140 mg, 17percent) as a white solid. ?H NMR (400 MHz, CDC13) oe 7.90 (d, J=2.1 Hz, 1H), 7.74 (ddd, J=8.0, 6.5, 1.7 Hz, 1H), 7.52 – 7.44 (m, 1H), 7.24 (d, J=0.9 Hz, 1H), 7.17 (t, J2.0 Hz, 1H), 6.34 (s, 1H),3.97 (d, J=0.7 Hz, 6H), 2.32 (s, 3H); LCMS (M+H) = 376.3; HPLC RT = 2.23 mm(Column: Chromolith ODS S5 4.6 x 50 mm; Mobile Phase A: 10:90 MeOH:water with0.1percent TFA; Mobile Phase B: 90:10 MeOH :water with 0.1percent TFA; Temperature: 40 °C;Gradient: 0-100percent B over 4 mm; Flow: 4 mL/min).

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; DELUCCA, George V.; GAVAI, Ashvinikumar V.; QUESNELLE, Claude A.; GILL, Patrice; O’MALLEY, Daniel; VACCARO, Wayne; LEE, Francis Y.; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; FANG, Haiquan; HILL, Matthew D.; HUANG, Hong; SCHMITZ, William D.; STARRETT, JR, John E.; HAN, Wen-Ching; TOKARSKI, John S.; MANDAL, Sunil Kumar; WO2015/100282; (2015); A1;,
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