Month: March 2021

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. 110661-91-1, name is tert-Butyl 4-bromobutanoate, A new synthetic method of this compound is introduced below., name: tert-Butyl 4-bromobutanoate

Step 1: Synthesis of ethyl 3-((1-(1-(4-(tert-butoxy)-4-oxobutyl)- 1H-pyrazol-4-yl)-6-chloro-2- cyclopropyl-7-fluoro- 1H-indol-3-yl)thio)-2-fluorobenzoate (2):1003731 To a stirred solution of indole 1 (Example 11, Step 3; 200 mg, 0.42 mmol) in DMF (5 mL) under inert atmosphere were added Cs2CO3 (206 mg, 0.63 mmol) and tert-butyl 4- bromobutanoate (141 mg, 0.63 mmol) at RT and stirred for 16 h. The mixture was diluted with ice cold water (20 mL) and extracted with EtOAc (3 x 30 mL). The combined organic extracts were dried (Na2504), filtered and concentrated under reduced pressure to obtain the crude. This was purified (silica gel chromatography; 20% EtOAc/ hexanes) to afford compound 2 (180 mg, 70%) as a pale brown oil. 1H NMR (400 MHz, CDC13): 5 7.67 (s, 1H), 7.64 (s, 1H), 7.63-7.60 (m, 1H), 7.18 (d,J= 8.4 Hz, 1H), 7.10-7.06 (m, 1H), 6.93 (t,J 8.0 Hz, 1H), 6.77 (t,J 7.6 Hz, 1H), 4.41 (q, 2H), 4.28 (t,J= 6.8 Hz, 2H), 2.28-2.19 (m, 4H), 1.74-1.66 (m, 1H), 1.46 (s, 9H),1.41 (t, J= 7.2 Hz, 3H), 1.06-1.02 (m, 2H), 0.89-0.84 (m, 2H); LC-MS (ES): m/z 618.6 (M + Hj.

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; PHARMAKEA, INC.; HUTCHINSON, John, Edward; LONERGAN, David; WO2015/77503; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 59247-47-1,Some common heterocyclic compound, 59247-47-1, name is tert-Butyl 4-bromobenzoate, molecular formula is C11H13BrO2, 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.

Step A: tert-Butyl 4-(1-cyano-2-methoxy-2-oxoethyl)benzoate. To a mixture of Na3PO4 (9.84 g, 60.0 mmol), methyl cyanoacetate (2.38 g, 24.0 mmol), and tert-butyl 4-bromobenzoate (5.14 g, 20.0 mmol) were added Pd(dba)2 (575 mg, 1.00 mmol), toluene (60 mL), and P(t-Bu)3 (10percent wt in hexanes, 11.56 mL, 3.89 mmol). After degassing for 20 minutes, the reaction was stirred at 80¡ã C. for 16 h. The resulting mixture was diluted with EtOAc, washed with H2O and brine, dried (MgSO4), and concentrated. Flash chromatography on silica gel (0-15percent EtOAc/hexanes) gave tert-butyl 4-(1-cyano-2-methoxy-2-oxoethyl)benzoate as a white solid. 1H NMR (CDCl3) delta8.02 (d, J=7.9 Hz, 2H), 7.51 (d, J=8.2 Hz, 2H), 4.79 (s, 1H), 3.79 (s, 3H), 1.58 (s, 9H). MS (ESI) calcd [M+H]+ 276.1, found 276.1.

The synthetic route of 59247-47-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Grimm, Jonathan B.; Hubbs, Jed L.; Miller, Thomas; Otte, Karin M.; Siliphaivanh, Phieng; Stanton, Matthew G.; Wilson, Kevin; Witter, David; Zhou, Hua; US2009/69250; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 619-42-1, name is Methyl 4-bromobenzoate, 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 619-42-1, HPLC of Formula: C8H7BrO2

[0246] Step 1: 4-Bromobenzohydrazide : To a stirred solution of methyl 4- bromobenzoate (10 g, 46.51 mmol) in methanol (200 mL) was added hydrazine hydrate (23.2 g, 465.1 mmol) at rt. The mixture was then refluxed for 16 h. The mixture was concentrated, diluted with water (70 mL) and extracted with ethyl acetate (3 X 70 mL). The combined organic layers were washed with brine (30 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was triturated with diethyl ether (30 mL) to afford 4-bromobenzohydrazide (8 g, 37.38 mmol, 80% yield ) as an off white solid . XH NMR (300 MHz, DMSO-d6) delta 7.68-7.53 (m, 4H), 7.38 (br s, 1H), 4.10 (br+2H]+.

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; KALYRA PHARMACEUTICALS, INC.; HUANG, Peter Qinhua; KAHRAMAN, Mehmet; SLEE, Deborah, Helen; BUNKER, Kevin, Duane; HOPKINS, Chad, Daniel; PINCHMAN, Joseph, Robert; ABRAHAM, Sunny; SIT, Rakesh, Kumar; SEVERANCE, Daniel, Lee; (248 pag.)WO2016/161160; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 868-72-4,Some common heterocyclic compound, 868-72-4, name is Dimethyl 2,5-dibromohexanedioate, molecular formula is C8H12Br2O4, 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 dimethyl 2, 5-dibromohexanedioate (SM) (20 g, 60.2 mmol) in THF (80 mL) was added methylamine (2M solution in THF) (90 mL, 180.7 mmol) slowly at 0 C under nitrogen atmosphere and then stirred for 30 min. The reaction mixture was allowed to RT and continued stirring for 16 h. After consumption of the starting material (by TLC), reaction mixture was filtered and the filtrate was evaporated under reduced pressure. Obtained crude mixture was purified by column chromatography by eluting 20% EtOAC/n-hexane to afford compound 1 (8 g, 60 %) as pure syrup. ^-NMR: (500 MHz, CDC13): delta 3.76 (s, 6H), 3.23 (br s, 2H), 2.56 (s, 3H), 2.19-2.08 (m, 4H). LCMS (m/z): 202.1 [M++l].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Dimethyl 2,5-dibromohexanedioate, its application will become more common.

Reference:
Patent; APTINYX INC.; KHAN, Amin, M.; (197 pag.)WO2018/26792; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 792-74-5, name is Dimethyl [1,1′-biphenyl]-4,4′-dicarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of Dimethyl [1,1′-biphenyl]-4,4′-dicarboxylate

The detailed procedure is as follows; to the solution of MBPDC (600 mg, 2.22 mmol) in 40 mL acetic acid, 20 mL of4:1 (v/v) H2SO4/H2O solution was added. Then the reaction mixture was refluxed for 24 h at 120C. The product was washed thoroughl ywith ethanol and dried in oven at 80¡ãC overnight (Yield: 520 mg,96.6percent).

The synthetic route of 792-74-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Medabalmi, Veerababu; Ramanujam, Kothandaraman; Journal of the Electrochemical Society; vol. 164; 7; (2017); p. A1720 – A1725;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 2318-25-4, These common heterocyclic compound, 2318-25-4, name is Ethyl 3-ethoxy-3-iminopropionate hydrochloride, 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 3C; Preparation of 2-ethoxy-8-thiomethyl-4-hydroxyquinoline (3C4); Step A; The imidate salt 3A2 (1.4 g, 7.2 mmol, 1 eq.) was combined with 2-(methylthio)aniline EPO 3C1 (0.96 g, 7.50 mmol, 1 eq.) in ethanol (15 ml.) under an N2 atmosphere. The reaction mixture was stirred at RT. (1 h) and monitored by HPLC. The reaction mixture was concentrated and then ether was added and the mixture filtered. The solids were washed with ether and the combined ether washes concentrated in vacuo. The resulting adduct 3C2 was obtained as a yellow oil (1.66 g, 82percent) and used as is in the next step. MS electrospray: (M + H)+; 282 and (M – H)”; 280.

Statistics shows that Ethyl 3-ethoxy-3-iminopropionate hydrochloride is playing an increasingly important role. we look forward to future research findings about 2318-25-4.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; BOEHRINGER INGELHEIM PHARMA GmbH & CO KG; WO2007/9227; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 56741-34-5, 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. 56741-34-5, name is Methyl 5-amino-2-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

Step 3 Preparation of 1-[1-(2-toluoylmethyl)-2-oxo-5-pivaloyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-methoxycarbonyl-4-fluorophenyl)urea Methyl 5-amino-2-fluorobenzoate (241 mg) was dissolved in tetrahydrofuran (43 ml), under ice-cooling triphosgene (142 mg) was added and triethylamine (123 mul) were added five times every 3 minutes, a solution of 1-(2-toluoylmethyl)-2-oxo-3-amino-5-pivaloyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (528 mg) in tetrahydrofuran (20 ml) was added thereto, and the mixture was allowed to come to room temperature and stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, water (50 ml) was added, and extracted with methylene chloride. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography(n-hexane:ethyl acetate=2:1), to thereby obtain 543 mg of the titled compound (Yield: 69.3%). 1H-NMR(CDCl3) delta: 1.05(9H, s), 2.39(3H, s), 2.47(3H, s), 3.84(3H, s), 3.84-3.39(1H, m), 4.39(1H, t), 4.45(1H, d), 4.84-4.92(1H, m), 5.55(1H, d), 6.57(1H, d), 6.91(1H, dd), 7.02(1H, s), 7.11-7.29(4H, m), 7.38-7.45(3H, m), 7.68(1H, d), 7.86(1H, dd)

The chemical industry reduces the impact on the environment during synthesis Methyl 5-amino-2-fluorobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Zeria Pharmaceutical Co., Ltd.; US6239131; (2001); B1;,
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. 4897-84-1, name is Methyl 4-bromobutanoate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Methyl 4-bromobutanoate

Triphenyl phosphine (13.2 g, 50.2 mmol) was added to a solution of methyl 4-bromobutyrate (9.84 g, 52.7 mmol) in 200 ml dry THF and refluxed for 3 days. White solid precipitated from the solution; the reaction mixture was used in the next step without further purification.

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 4897-84-1.

Reference:
Patent; ArQule, Inc.; US6753449; (2004); B2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 206548-14-3, A common heterocyclic compound, 206548-14-3, name is Methyl 2-amino-5-bromo-3-methylbenzoate, molecular formula is C9H10BrNO2, 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 solution of 5.0g (0.021 mol) of 2-amino-5-bromo-3-methyl-benzoic acid methyl ester and 2.8g (0.023 mol) of phenyl boronic acid in 150 mL of dimethoxyethane was added 20.5 mL of a 2.0M aqueous solution of Na2CO3 and 1.18g (1.02 mmol) of Pd(PPh3)4. The reaction mixture was evacuated and filled with N2 three times and was then heated to reflux overnight. The reaction was then cooled to room temperature, and poured into ethyl acetate and water. The aqueous layer was extracted three times with ethyl acetate. The combined organics were washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was chromatographed on silica gel using gradient elution (100% hexane to 4/1 hexane/ethyl acetate) to provide 2.5 g (50%) of 4-amino-5-methyl-biphenyl-3-carboxylic acid methyl ester. Electrospray Mass Spec: 241.8 (M+H)+

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; Wyeth Holdings Corporation; EP1144369; (2004); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 454-31-9, 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. 454-31-9, name is Ethyl 2,2-difluoroacetate, This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution ofbicyclo[3. l.0]hexan-3-one (125 g, 1274 mmol) in THF (1500 mL) under N2 atmosphere at -78 C was added LDA (2.0 M in THF, 0.701 L, 1402 mmol). The solution was stirred for 1 h at -78 C. To the solution was added slowly over 30 minutes a solution of ethyldifluoroacetate (174 g, 1402 mmol) in THF (300 mL) maintaining a temperature of -78 C. The reaction mixture was allowed to warm to 27 C and was then stirred for 1 h. Progress of the reaction was monitored by TLC (SiC, 20% Acetone/Hexane, Rf = 0.3, UV -active). The reaction mixture was quenched via the addition of aq. HC1 (1N, 2000 mL). The mixture was stirred for 30 min. and then was extracted with EtOAc (3 x 1000 mL). The combined organic layers were washed with brine (1000 mL), dried over anhydrous NaiSCL and filtered. The filtrate was concentrated under reduced pressure to afford 2-(2,2-difluoroacetyl)bicyclo[3. 1.0]hexan-3-one as a pale yellow viscous liquid, 180 g (71%). NMR (400 MHz, CDCb) d = 6.18 (t, J= 54.8 Hz, 1H), 2.70 – 2.62 (m, 1H), 2.35 (d, J= 19.4 Hz, 1H), 2.14 (br s, 1H), 1.26 – 1.21 (m, 1H), 1.04-1.03 (m, 1H), 0.22-0.21 (m, 1H), LCMS: M/Z = 173.17).

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

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BOWSHER, Michael S.; GILLIS, Eric P; PARCELLA, Kyle E.; (0 pag.)WO2020/89778; (2020); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics