Month: May 2021

Some common heterocyclic compound, 2398-37-0, name is 1-Bromo-3-methoxybenzene, molecular formula is C7H7BrO, 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 2398-37-0

General procedure: Compound 7a was prepared by reacting 3-bromo-2-methyl-5-thienylboronic acid (3.0g, 11.3mmol) with 3-bromobenzonitrile (2.47g, 13.6mmol) in the presence of Pd(PPh3)4 (0.15g, 0.01mmol) and Na2CO3 (2.0 mol L-1, 50 mL) in tetrahydrofuran (THF) (80mL containing 10% water). After refluxing for 16h, the product was extracted with diethyl ether. The organic layer was dried over MgSO4, filtrated, and evaporated. The crude product was purified by column chromatography on SiO2 using petroleum ether as the eluent and 2.0g of 7a obtained as a yellowish solid in 53% yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2398-37-0, its application will become more common.

Reference:
Article; Wang, Renjie; Pu, Shouzhi; Liu, Gang; Chen, Bing; Tetrahedron; vol. 69; 26; (2013); p. 5537 – 5544;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 36865-41-5,Some common heterocyclic compound, 36865-41-5, name is 1-Bromo-3-methoxypropane, molecular formula is C4H9BrO, 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 mixture of 51d (1.00 g, 1 eq) in DMSO (8 mL), is added Cs2CO3 (3.51 g, 3 eq). After stirring for 5 min, 2-bromoethyl methylether (0.62 mL, 1.5 eq) is added and the solution is stirred at RT during 18 h. The reaction mixture is quenched with H2O, extracted with EtOAc (3×), the combined organic extracts are washed with H2O (3×), brine, dried over Na2SO4 and concentrated. The resulting residue is purified by flash chromatography Hex/EtOAc (1:1) to give 51e (1.20 g, 98%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-3-methoxypropane, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2010/261714; (2010); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 4179-19-5, name is 3,5-Dimethoxytoluene, belongs to ethers-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 4179-19-5, HPLC of Formula: C9H12O2

1,3-dimethoxy-5-methylbenzene (30 g, 0.20 mol) and dichloromethane (900 mL) were added to a dry round bottom flask (1 L) and cooled to the above solution in an ice bath. Disulfone chloride (52.5 g, 0.40 mol) was added dropwise, and the mixture was added dropwise and stirred at room temperature overnight. After the reaction was completed, an aqueous solution of sodium hydrogencarbonate was added dropwise to adjust pH = 8, and dichloromethane was extracted with dilute hydrochloric acid, respectively.Washed with distilled water,Drying and concentration under reduced pressure gave compound 2,4-dichloro-1,5-dimethoxy-3-methylbenzene (31 g, white solid).

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, 3,5-Dimethoxytoluene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Rudong Lingda Bio-pharmaceutical Technology Co., Ltd.; Wang Hui; (35 pag.)CN109721599; (2019); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 157869-15-3,Some common heterocyclic compound, 157869-15-3, name is 2-((4-Methoxyphenyl)ethynyl)aniline, molecular formula is C15H13NO, 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.

General procedure: A sealed tube was charged with the mixture of 2-alkynylaniline 1 (1 mmol), carbon disulfide (1.5 mmol), then stirred in a solution of DBUH+ in CH3CN (1.5 mL) at room temperature under nitrogen atmosphere for indicated time. After completion, then H2O (5 mL) was added and the mixture was extracted with EtOAc (5 mL x 3), dried by anhydrous Na2SO4. Evaporation of the solvent followed by purification on silica gel (petroleum ether/ethylacetate = 4/1) provided the corresponding product 2.

The synthetic route of 157869-15-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhao, Peng; Liao, Qian; Gao, Hongxin; Xi, Chanjuan; Tetrahedron Letters; vol. 54; 19; (2013); p. 2357 – 2361;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, belongs to ethers-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 41789-95-1, Formula: C9H13NO

Example 11 2-((3-methoxy-N-methybenzylamino)methyl)-1H-anthra[1,2-d]imidazole-6,11-dione (CL09) Compound CL01 (1.18 g, 4 mmole) and DIPEA (1.4 mL, 8 mmole) were stirred in 30 mL anhydrous tetrahydrofuran (THF) for 10 minutes. Then, 3-methoxy-N-methybenzylamine (1.19 mL, 8 mmole) was added thereto. The mixed solution was reacted by heating under reflux for 6 hours. After completion of reaction, the mixed solution was concentrated under reduced pressure (by reduced pressure concentrator such as Vacuum Evaporator). Then the concentrated mixture was extracted with ethyl acetate/H2O. The extract was dried by MgSO4 and concentrated under reduced pressure to obtain a crude product. The crude product was recrystallized in ethyl acetate/n-hexane, the mixture was filtered to collect the crystal which was rinsed with acetone to obtain a yellowish brown compound. Mol. Wt.: 411.4525 (C25H21N3O3); Yield: 39%; Mp: 150-151 C.; Rf: 0.79 (ethyl acetate:dichloromethane:methanol=2:2:1); HRMS (ESI) m/z calcd for C25H21N3O3+[M]+: 411.1583. Found: [M+H]+=412.1701, [M+Na]+=434.1519. 1H-NMR (300 MHz, CDCl3) delta (ppm): 2.44 (s, 3H, -N-CH3), 3.74 (s, 2H, -CH2-), 3.86 (s, 3H, -O-CH3), 4.01 (s, 2H, -CH2-), 6.83 (d, J=7.8 Hz, 1H, Ar’-H), 7.03-7.00 (m, 2H, Ar’-H), 7.27 (t, J=6.9 Hz, 1H, Ar’-H), 7.77-7.80 (m, 2H, Ar-H8,9), 7.99 (d, J=8.4 Hz, 1H, Ar-H4), 8.17 (d, J=8.1 Hz, 1H, Ar-H5), 8.23-8.32 (m, 2H, Ar-H7,10); 13C-NMR (75 MHz, CDCl3) delta (ppm): 29.15, 42.87, 54.97, 55.27, 62.17, 113.85, 114.55, 118.40, 121.54, 121.64, 125.53, 126.63, 127.62, 128.82, 129.74, 130.13, 132.61, 133.53, 133.82, 134.13, 134.33, 149.00, 160.23, 182.99, 184.88.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(3-Methoxyphenyl)-N-methylmethanamine, and friends who are interested can also refer to it.

Reference:
Patent; HUANG, Hsu-Shan; US2011/207719; (2011); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 59557-91-4, The chemical industry reduces the impact on the environment during synthesis 59557-91-4, name is 4-Bromo-2-methoxyaniline, I believe this compound will play a more active role in future production and life.

4-(Dipropylphosphoryl)-2-methoxyaniline To a solution of 4-bromo-2-methoxyaniline (0.100 g, 0.495 mmol) in 2 mL DMF was added dipropylphosphine oxide (0.0730 g, 0.544 mmol), palladium acetate (5.6 mg, 0.025 mmol), XANTPHOS (17.2 mg, 0.030 mmol), and potassium phosphate (0.116 g, 0.544 mmol). The mixture was purged with nitrogen, and subjected to microwaves at 150 C. for 20 minutes. The reaction mixture was concentrated and purified by silica gel chromatography (0-12% 7N ammonia in methanol:dichloromethane) and the fractions were concentrated. The residue was acidified with 2.5 M HCl in ethanol and the solution was concentrated to provide 4-(dipropylphosphoryl)-2-methoxyaniline as the hydrochloride salt (0.132 g, 91% yield).

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, 4-Bromo-2-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARIAD PHARMACEUTICALS, INC.; Wang, Yihan; Huang, Wei-Sheng; Liu, Shuangying; Shakespeare, William C.; Thomas, Ranny M.; Qi, Jiwei; Li, Feng; Zhu, Xiaotian; Kohlmann, Anna; Dalgarno, David C.; Romero, Jan Antoinette C.; Zou, Dong; US2015/225436; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, belongs to ethers-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. Product Details of 1462-37-9

Step-1: 1-(2-(benzyloxy)ethyl)-4-iodo-lH-pyrazoleTo a stirred solution 4-iodo-lH-pyrazole (2.0 g, 10.3 mmol) in DMF (20 ml) was addedpotassium carbonate (3.5 g, 25 mmol) followed by drop wise addition of ((2-bromoethoxy)methyl)benzene (2.43 g, 11 mmol) and stirred the reaction at RT for 15 h. Thereaction was monitored by TLC (50percent ethyl acetate in hexane). The reaction mixture was dilutedwith ice water (150 ml) and extracted with ethyl acetate (2×50 ml). The organic layer was driedover Na2S04, and concentrated under reduced pressure to afford 3.1 g (91.7percent yield) of 1-(2-fluorobenzyl )-4-iodo-1 H-pyrazole.1H NMR (DMSO-d6, 300MHz): 8 7.29 (s, lH), 7.55 (s, lH), 7.37-7.22 (m, SH), 4.45 (s, 2H),4.34-4.30 (t, 2H), 3.77-3.74 (t, 2H); LCMS: rn/z = 329.1 (M+l).

The synthetic route of 1462-37-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; UM PHARMAUJI SDN. BHD; GUMMADI, Venkateshwar Rao; HOSAHALLI, Subramanya; NANDURI, Srinivas; AGGUNDA RENUKAPPA, Girish; WO2014/24077; (2014); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 74654-07-2, name is 2-(2-(2-Methoxyethoxy)ethoxy)ethanamine, belongs to ethers-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 74654-07-2, Quality Control of 2-(2-(2-Methoxyethoxy)ethoxy)ethanamine

Example 56A tert-Butyl [(trans-4-{[(2S)-3-[5′-({2-[2-(2-methoxyethoxy)ethoxy]ethyl}carbamoyl)-2′-methylbiphenyl-3-yl]-1-oxo-1-{[4-(1H-tetrazol-5-yl)phenyl]amino}propan-2-yl]carbamoyl}cyclohexyl)methyl]carbamate 3′-[(2S)-2-{[(trans-4-{[(tert-Butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]amino}-3-oxo-3-{[4-(1H-tetrazol-5-yl)phenyl]amino}propyl]-6-methylbiphenyl-3-carboxylic acid (100 mg, 0.15 mmol) and 2-[2-(2-methoxyethoxy)ethoxy]ethanamine (29 mg, 0.17 mmol) were dissolved in tetrahydrofuran (4 ml), N-[(dimethylamino)(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylidene]-N-methylmethanaminium hexafluorophosphate (67 mg, 0.17 mmol) and N,N-diisopropylethylamine (23 mg, 0.17 mmol) were added and the mixture was stirred at RT overnight. Subsequently, the mixture was concentrated and the residue was purified chromatographically by HPLC (Method 10). This gave 45 mg (37% of theory) of the title compound. LC-MS (Method 4): Rt=1.20 min; MS (ESIpos): m/z=827.6 [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, 2-(2-(2-Methoxyethoxy)ethoxy)ethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; ROeHN, Ulrike; ELLERMANN, Manuel; STRASSBURGER, Julia; WENDT, Astrid; ROeHRIG, Susanne; WEBSTER, Robert Alan; SCHMIDT, Martina Victoria; TERSTEEGEN, Adrian; BEYER, Kristin; SCHAeFER, Martina; BUCHMUeLLER, Anja; GERDES, Christoph; SPERZEL, Michael; SANDMANN, Steffen; HEITMEIER, Stefan; HILLISCH, Alexander; ACKERSTAFF, Jens; TERJUNG, Carsten; (163 pag.)US2016/244437; (2016); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 1535-73-5, name is 3-Trifluoromethoxyaniline, belongs to ethers-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 1535-73-5, Safety of 3-Trifluoromethoxyaniline

(a) Synthesis of 4-bromo-3-(trifluoromethoxy)aniline A solution of N-bromosuccinimide (3.78 g, 21.2 mmol) in N,N-dimethylformamide (11 ml) was added dropwise to a solution of 3-trifluoromethoxyaniline (3.84 g, 21.2 mmol) in N,N-dimethylformamide (11 ml) at room temperature over a period of 40 minutes. After completion of the dropwise addition, the resulting mixture was stirred overnight. After completion of the reaction, the reaction mixture was poured into water and extracted with ethyl acetate, and the organic layer was dried over magnesium sulfate and filtered. The filtrate was concentrated and the crude product thus obtained was purified by a silica gel column chromatography (hexane/chloroform = 6/4) to obtain 4-bromo-3-(trifluoromethoxy)aniline (4.96 g, 91percent).

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

Reference:
Patent; Sumitomo Pharmaceuticals Company, Limited; EP1500643; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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 2062-98-8 as follows. Computed Properties of C6F12O2

General procedure: To a magnetic stirred solution of 15.6 g triethylamine (0.15 mol) and 10.10 g allyl alcohol (0.17 mol) in anhydrous chloroform (150 mL) in a dry three-neck flask, 74.90 g perfluoro-2,5-dimethyl-3,6-dioxa-nonanoyl fluoride (0.15 mol) were added dropwise over a period of 3 h under agitation at 0 C. The reaction mixture was stirred for a further 12 h, with the temperature of reaction mass being maintained at room temperature. Distilled water was added to extract the triethylammonium fluoride and the unreacted allyl alcohol at the end of the reaction. The chloroform layer was dried over anhydrous sodium sulfate, and the major portion of the chloroform was distilled off in the vacuum of a water-jet pump over water. Additionally, the crude product was obtained and distilled under reduced pressure to give the pure product.

According to the analysis of related databases, 2062-98-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Shi, Xiang; Shi, Hongxin; Wu, Hongke; Shen, HaiMin; Research on Chemical Intermediates; vol. 44; 9; (2018); p. 5091 – 5105;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem