Month: June 2021

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. 34967-24-3, name is 3,5-Dimethoxybenzyl amine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H13NO2

General procedure: Synthesis of (2R, 3R, 4S, 5R)-2-(6-(benzylamino)-9H-purin-9-yl)-5-(hydroxymethyl) tetrahydrofuran-3,4-diol, 2. In a 7 mL MW vessel, 6-chloropurinoriboside 3 (20 mg, 0.07 mmol), benzylamine 4 (7.5 mg,0.07 mmol, 7.7 muL) and triethylamine (7.08 mg, 0.07 mmol, 9.8 muL)were mixed. The solid mixture was stirred in CEM Explorer. MWMethod: T = 210 C, Power: 300 W, Hold Time: 1 min, P = 250 PSI,Power Max activated. After cooling, the solvent was removed in vacuoand the crude was dissolved in methanol and then purified on PTLC(DCM/MeOH 9:1) to afford compound 2 as white solid (24 mg, 94%).C17H20N5O4: 358.1510; Found 358.1515. Rt: 8.92 min.

According to the analysis of related databases, 34967-24-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Abate, Mario; Bifulco, Maurizio; Buonocore, Michela; Ciaglia, Elena; Covelli, Verdiana; D’Ursi, Anna Maria; Gazzerro, Patrizia; Grimaldi, Manuela; Randino, Rosario; Rodriquez, Manuela; Scrima, Mario; Stillitano, Ilaria; Tosco, Alessandra; Bioorganic Chemistry; (2020);,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 944317-92-4, 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. 944317-92-4, name is 1-Bromo-4-fluoro-5-isopropyl-2-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A 500 mL dry flask was charged with 2-bromo-5-fluoro-4-isopropylanisole (compound of formula 4, Scheme 3) (24.6 g, 0.1 mol) and dissolved in toluene (80 mL) and THF (80 mL). The resulting solution was flushed with argon, and tri-isopropylborate (32 mL, 0.14 mol) was added. The mixture was cooled to -80 C. Then 10 M n-BuLi in hexanes (12.5 mL, 0.125 mol) was added slowly, maintaining a temperature below -55C. Thirty minutes after completion of the n-BuLi addition, the reaction was warmed to -35C and quenched into 3 M H2S04 solution (75 mL, 0.225 mol). DIPE (200 mL) was added to the mixture to dilute the organic layer. The mixture was stirred (15 min) and the aqueous layerwas cut away. The organic layerwas washed with 3.0 M H2S04 (75 mL). The organic phase was extracted three times with 1 M NaOH (200 mL first and then 50 mL and 50 mL). The three NaOH extractions were combined, diluted with 2-propanol (85 mL), and cooled to 15 “C. Then the solution was slowly acidified to pH ~ 2 using 3 M H2SO4 (70 mL) while maintaining temperature at 15-20 C. The resulting slurry was stirred for 1 hour and then filtered. The filter cake was washed with water (3 x 30 mL) and dried under an air flow for 1 day. The filtered solid was placed in an oven under vacuum at 50 C for 2-3 days to decompose a diaryl impurity and to dry the solid. The white crystalline solid was isolated to yield boronic acid of formula 5 (Scheme 3) (19.23 g, 91 %): mp 100-102 C; H NMR (CDCI3) delta 1.25 (d, J = 6.9 Hz, 6H), 3.17 (sept, J = 6.9 Hz, 1 H), 3.88 (s, 3H), 5.83 (S, 2H), 6.59 (d, J = 12 4 Hz, 1 H), 7.72 (d, J = 6.6 Hz, 1 H). The impurity 5-ethyl-4-fluoro-2-methoxyphenylboronic acid (-4%), which is formed from 1-bromo-5-ethyl-4-fluoro- 2-methoxybenzene (BrMET) present in the starting material under the conditions described in Step 4, was detected in the product.

The synthetic route of 1-Bromo-4-fluoro-5-isopropyl-2-methoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LEK PHARMACEUTICALS D.D.; HUMLJAN, Jan; MARAS, Nenad; WO2013/91696; (2013); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C10H13BrO

Magnesium (317.2 mg, 13.05 mmol) was suspended in 5 mL of ether, a solution of 2.30 mL (13.0 mmol) of 3-benzyloxypropyl bromide in 7 mL of ether was dropped into the suspension over 10 minutes, a flake of iodine was added thereto and the mixture was heated to reflux for 1 hour. The reaction mixture was cooled with an ice-methanol bath, a solution of 5.1 mg (0.011 mmol) of N-methoxy-N-methyl-(1-methylindole)-2-carboxamide in tetrahydrofuran was added thereto and the mixture was stirred at 0°C for 2 hours. Ice water was added to the reaction solution and the mixture was acidified with 6 mol/L hydrochloric acid and extracted with ether. The organic layer was washed with water and a saturated aqueous saline solutio dried over anhydrous sodium sulfate and the solvent was evaporated. The residue was purified with a silica gel column chromatography (hexane/ethyl acetate = 8/1) to give 0.79 g (54percent) of 2-(4-benzyloxy-1-oxobutyl)-1-methylindole.1H-NMR(270MHz, DMSO-d6, delta); 2.09(m, 2H), 3.10(t, J=7.3Hz, 2H), 3.58(t, J=6.1Hz, 2H), 4.05(s, 3H), 4.50(s, 2H), 7.15(m, 1H), 7.26-7.39(m, 8H), 7.69(dd, J=1.0Hz, 8.3Hz, 1H). Fab-MS(m/z); 308[M+1]+

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 54314-84-0.

Reference:
Patent; KYOWA HAKKO KOGYO CO., LTD.; EP1464645; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 93919-56-3, 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. 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

6-Methoxy-5-({[4-(trifluoromethoxy)benzyl]amino}methyl)-2-naphthoic acid methyl ester To a stirred solution of 6-methoxy-5-formyl-2-naphthoic acid methyl ester (1.09 g, 4.46 mmol) in EtOH (40 ML) at room temperature was added 4-trifluoromethoxy-benzyl amine (0.749 ML, 4.91 mmol) followed by HOAc (0.255 ML, 4.46 mmol).After 10 min. at this temperature, sodium cyanoborohydride (0.420 g, 6.69 mmol) was added, and reaction was continued stirring at rt for 4 h.After 1 h at this temperature, the reaction was heated to 45 C. for 2 h.The solution was quenched with sat. aq. NaHCO3 (20 ML) and then extracted with EtOAc (200 ML).The organic layer was washed with brine (20 ML) and dried (MgSO4).After concentration, the residue was purified by flash chromatography (0 to 10% MeOH:CHCl3 gradient) to afford the product (0.780 g, 42%) as a solid; 1H NMR (DMSO-d6) delta3.77 (s, 2H), 3.86 (s, 3H), 3.88 (s, 3H), 4.07 (s, 2H), 7.26 (d, J =8.0 Hz, 2H), 7.44 (d, J=8.6 Hz, 2H), 7.48 (d, J=9.2 Hz, 1H), 7.88 (dd, J=1.9, 8.9 Hz, 1H), 8.06 (d, J=5.2 Hz, 1H), 8.08 (d, J=5.3 Hz, 1H), 8.52 (d, J=1.7 Hz, 1H); mass spectrum [(+) El], m/z 420 (M+H)+.

The synthetic route of (4-(Trifluoromethoxy)phenyl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wyeth; US2004/127570; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 53087-13-1, These common heterocyclic compound, 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, 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.

Step3. 4-(4-morpholinyl)-1-{3-[(phenylmethyl) oxy] phenyl}-1-butanone Under argon, to a solution of 1-bromo-3-[(phenylmethyl) oxy] benzene (2.04 g, 7.76 mmol) in THF (30 mL) at-78 C, was added dropwise n-BuLi (5.1 mL, 1.6 M in Hexanes), 20 min after the addition, this solution was added to a solution the product from Step 3 (1.68 g, 7.76 mmol) in THF (30 mL) under argon at-78 C. 15 min later, the reaction mixture was slowly warmed to 0 C. The reaction mixture was poured into a mixture of EtOAC and NH4C1, then extracted with EtOAC (2X), organic layers were combined, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was then purified with flash chromatography (hexanes/ethyl acetate 1: 4), to afford the title compound as a colorless oil (932 mg, 35%).

The synthetic route of 53087-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2005/37197; (2005); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 62257-15-2, 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 62257-15-2 as follows.

To a mixture of 2-fluoro-5-methoxyaniline (5.0 g, 35 rnmol), sulfuric acid (7.5 niL), trifluoroacetic acid (37.5 mL) and water (45 mL) was added NaNO2 (3.7 g, 53 mmoi)portionwise at 0 C. The mixture was stirred for 30 mm at 0 C and NaN3 (4.6 g, 71 mmol) was added. The resulting solution was stirred overnight at RT and extracted with EtOAc (2 x 200 mL), The combined organic layers were dried over Na2SO4 and concentrated. The residue obtained was purified by column chromatography on silica gel (EtOAc/petroleum ether, 1100) to give compound 5a as a light yellow oil. ?H-NMR (300MHz, DMSO-d6) d (ppm): 723 (dd, Ji = 9.0 Hz, J2= 10.8 Hz. 1H), 6.72 – 6.80 (m, 2H),3.76 (s, 3H). Mass Spectrum (GCMS. Efl: Calcd. ?for C7H6FN3O: 167.0 (M); found: 167.2

According to the analysis of related databases, 62257-15-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; HUANG, Hui; MEEGALLA, Sanath; PLAYER, Mark R.; (212 pag.)WO2017/27312; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 588-63-6, name is (3-Bromopropoxy)benzene, A new synthetic method of this compound is introduced below., Computed Properties of C9H11BrO

2,4-diamino-5-hydroxy -1, 3, 5-tri-aza-9-oxa-spiro [5.5] undecane -1,3-diene-hydrochloride (0.47g, 0 . 002mol), sodium hydroxide (0.08g, 0 . 002mol), methanol 10 ml in mixed in the round-bottom flask, heating to reflux 30 minutes, the heat filters, concentrating the filtrate. By adding 1-bromo-3-phenoxy-propane (0.52g, 0 . 0024mol) and DMF2ml, stirring the mixture at room temperature. When consumes TLC monitoring raw materials, into a small amount of thick hydrogen PH value in order to adjust the bromate 2-3. Remove the solvent under reduced pressure, to obtain white solid, with ethanol: water = 10:1 ( volume ratio ) recrystallization, get white crystal 0.26g, yield 31.7percent, HPLC purity measured 99.6percent.

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; Shanghai Institute Of Pharmaceutical Industry(China State Institute of Pharmaceutical Industry); zhou, xiaotian; lin, kuaile; zhou, Weicheng; (41 pag.)CN103664972; (2016); B;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 38336-04-8, 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. 38336-04-8 name is 2-(Benzyloxy)-1-ethanamine, 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.

To a stirred solution of 16 (2.30 g, 7.20mmol) in toluene (45 mL) were added 2-phenylmethoxyethanamine 1717 (1.24 g, 8.19 mmol), sodiumtert-butoxide (2.09 g, 21.7 mmol), Pd2(dba)3 (336 mg, 0.367 mmol), and (S)-BINAP (547 mg, 0.879mmol). After stirring at 80 C for 19 h, the reaction mixture was cooled to room temperature and thendiluted with Et2O (20 mL). The mixture was filtered through a Celite pad and the residue was washedwith Et2O for several times. The combined filtrate was concentrated under reduced pressure, and theresidue was purified by flash silica gel column chromatography (hexane/EtOAc = 30/1) to afford 19 (2.06g, 73%) as a white solid: Rf = 0.50 (hexane/EtOAc = 10/1); 1H NMR (400 MHz, CDCl3) delta 7.43-7.27 (m,10H), 6.79-6.68 (m, 3H), 5.06 (s, 2H), 4.55 (s, 2H), 3.74 (t, J = 5.5 Hz, 2H), 3.40 (t, J = 5.5 Hz, 2H), 1.29(s, 9H); 13C NMR (125 MHz, CDCl3) delta 144.5, 144.4, 138.3, 137.8, 137.5, 128.6, 128.5, 127.9, 127.7,127.6, 113.2, 110.7, 108.3, 73.1, 70.6, 68.8, 43.7, 34.4, 31.7 ppm; IR (ATR) numax: 3386, 3063, 2966, 2859,1604, 1451, 1391, 1213, 1035, 695, 650 cm-1; HRMS (ESI) [M+H+] calcd for C26H32NO2: 390.2428,found 390.2419; mp 56.7 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(Benzyloxy)-1-ethanamine, and friends who are interested can also refer to it.

Reference:
Article; Matsumoto, Yuri; Nakamura, Akihiko; Saito, Emi; Nakada, Masahisa; Heterocycles; vol. 97; 1; (2018); p. 232 – 252;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 592-55-2, 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. 592-55-2 name is 1-Bromo-2-ethoxyethane, 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.

To A solution of 1- (3-Methoxy-4-nitro-phenyl)-piperidin-4-ol (300mg, 1. 2 mmol) in N, N- dimethylformamide (3.0 mL), sodium hydride (1.52g, 3.8 MMOL) is added. After stirring, 2- bromethyl methyl ether (1501L1, 1.6 MMOL) is added and the mixture is further stirred at 70C for 15 hours. After addition of saturated aqueous ammonium chloride, the mixture is poured into water and extracted twice with ethyl acetate. The organic layer is washed with brine, dried over sodium sulfate, and evaporated in vacuo. The residue is purified by silica gel column chromatography (n-hexane-ethyl acetate gradient) to afford 4- (2-METHOXY-ETHOXY)-1- (3- METHOXY-4-NITRO-PHENYL)-PIPERIDINE (111 MG, 29%) as a yellow oil. ‘H-NMR (400MHZ, CDCI3, O, ppm): 1.52 (t, 3H), 1.95-2. 00 (m, 2H), 1.70-1. 79 (m, 2H), 3.23 (ddd, 2H), 3.58-3. 64 (m, 2H), 3.65-3. 68 (m, 2H), 3.64-3. 72 (m, 2H), 3.95 (s, 3H), 6.31 (d, 1H), 6.42 (dd, 1 H), 8.00 (d, 1 H). RF 0. 53 (n-hexane: AcOEt=1 : 1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2-ethoxyethane, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2004/80980; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

These common heterocyclic compound, 886762-08-9, name is 5-Bromo-2-(trifluoromethoxy)aniline, 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. Recommanded Product: 5-Bromo-2-(trifluoromethoxy)aniline

General procedure: To a solution of N-tosylhydrazone (0.6mmol, 1.1 eq) in distilled dioxane (8mL) was added bis(acetonitrile)palladium(II) chloride (0.05mmol, 5mol %), and dppp (0.1mmol, 10mol %). The resulting suspension was stirred RT for 2min, and cesium carbonate (1.5mmol, 3.0 eq) was added. Then, the reaction mixture was stirred for additional 2min, and aryl bromide (0.5mmol, 1.0 eq) was added in one portion. The mixture was then heated at 100C for 3h. The crude reaction mixture was allowed to cool to rt. EtOAc was added, and the mixture was filtrated through Celite. The solvent was evaporated under reduced pressure, and the crude product was purified by flash chromatography on silica gel.

The synthetic route of 5-Bromo-2-(trifluoromethoxy)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Article; Naret, Timothee; Bignon, Jerome; Bernadat, Guillaume; Benchekroun, Mohamed; Levaique, Helene; Lenoir, Christine; Dubois, Joelle; Pruvost, Alain; Saller, Francois; Borgel, Delphine; Manoury, Boris; Leblais, Veronique; Darrigrand, Romain; Apcher, Sebastien; Brion, Jean-Daniel; Schmitt, Etienne; Leroux, Frederic R.; Alami, Mouad; Hamze, Abdallah; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 473 – 490;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem