Tag: M.W=200-300

Reference of 210532-25-5,Some common heterocyclic compound, 210532-25-5, name is 3,5-Difluorobenzene-1-sulfonyl chloride, molecular formula is C6H3ClF2O2S, 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: In a round bottom flask under N2, 2-bromo-1-(1H-indol-3-yl)ethanone (1) (500 mg, 2.1 mmol), p-toluenesulfonyl chloride (439 mg, 2.3 mmol), DMAP (26 mg, 0.21 mmol), and triethylamine (0.3 mL, 2.1 mmol) were dissolved in 20 mL of dry CH2Cl2, and the solution was stirred at room temperature until that the starting material had disappeared by checking TLC. The reaction mixture was quenched by dilution with CH2Cl2 (30 mL), and the organic extract was washed with 1 N HCl (20 mL). The organic layer was dried over anhydrous Na2SO4, filtered and the solvent was removed under vacuum. The product was purified by silica gel column chromatography using CH2Cl2 to give 379 mg of (2a) as brown crystalline plates.

The synthetic route of 210532-25-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Vera, Gonzalo; Lagos, Carlos F.; Almendras, Sebastian; Hebel, Dan; Flores, Francisco; Valle-Corvalan, Gissella; Pessoa-Mahana, C. David; Mella-Raipan, Jaime; Montecinos, Rodrigo; Recabarren-Gajardo, Gonzalo; Molecules; vol. 21; 8; (2016);,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 1008361-80-5, name is 4-Bromo-3-chlorobenzene-1,2-diamine, 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. Application In Synthesis of 4-Bromo-3-chlorobenzene-1,2-diamine

Example 13 N2 -[(4-Chloro-lH-benzimidazol-5-yl)methyl]- N4 -(5-cyclopropyl-lH-pyrazol-3-yl)pyrimidine-2,4- diamine (1-3) step 1 : A mixture of 4-bromo-3-chloro-benzene-l,2-diamine (CASRN 1008361-80-5, 27 g, 0.1221 mol) and formic acid (80 mL) was heated to reflux for 1.5 h. After the completion of the reaction, 10% NaOH was added until the solution basic. The resulting solid was filtered and washed well with water then dried over night over suction to afford 22 g (78%) of 5-bromo-4-chloro-lH-benzoimidazole (128) as pale yellow solid which was used without additional purification.

The synthetic route of 4-Bromo-3-chlorobenzene-1,2-diamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; ALIAGAS-MARTIN, Ignacio; CRAWFORD, James; LEE, Wendy; MATHIEU, Simon; RUDOLPH, Joachim; WO2013/26914; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 16793-91-2, 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. 16793-91-2 name is 2-Chlorophenethyl Bromide, 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.

General procedure: Ethyl 2-piperidin-4-ylacetate 11 (1 g, 5.84 mmol, 1.0 equiv.) and substituted (2-romoethyl)benzene derivatives (12a-b) (7.01 mmol, 1.2 equiv.) were dissolved in 20 mL acetone.Then, anhydrous K2CO3 (11.68 mmol, 2 equiv.) and catalytic amount KI were added. The reactionmixture was refluxed for 4 h. After completion of the reaction, acetone was concentrated, and theresidue was dissolved in water (60 mL) and extracted with ethyl acetate (60 ¡Á 3 mL). The combinedorganic layers were dried over Na2SO4, filtered, and concentrated in vacuum. The obtained oil wasused in further synthesis without purification yielded compounds 13a-b (Yields were 67% and 72%).Then, 4 mol/L KOH (2.5 equiv.) was added to the solution of compounds 13a-b in C2H5OH: H2O =5:1(6 mL). The reaction mixture was stirred at room temperature for 7 h. After completion of the reaction, the reaction mixture was evaporated to dryness after neutralization with dilute hydrochloricacid solution. Poured into ethyl acetate to deposit the solid, after cooling off, the mixture was filteredand washed with cold ethyl acetate to give compounds 14a-d.Finally, intermediates (14a-b) (1.2 equiv.), PyBOP (1.2 equiv.) and DIPEA (1.5 equiv.) wereadded to 6 mL DMF and stirred at room temperature for 20 min. Then, intermediates (15a-b) (1.0equiv.) was added and stirred at room temperature for 4 h. After completion of the reaction, thereaction mixture was quenched with saturated NaCl solution. The aqueous phase was extracted withDCM. The DCM layer was combined and washed with brine solution. The organic layer was driedover anhydrous Na2SO4 and the solvent was removed under reduced pressure. After concentration,the crude product was purified by silica gel column chromatograph using a methanol indichloromethane gradient (DCM:methanol = 60:1-5:1) yielded compounds 16a-d.N-(1H-Indol-5-yl)-2-(1-phenethylpiperidin-4-yl)acetamide (16a). 2-(1-Phenethylpiperidin-4-yl) aceticacid (140 mg, 0.57 mmol), 1H-Indol-5-amine (63 mg, 0.48 mmol), PyBOP (295 mg, 0.57 mmol),DIPEA (93 mg, 0.72 mmol), DMF (6 mL). Yellow solid, m.p.: 165-167 C, yield: 80.70%, 1H NMR(400 MHz, CD3OD) delta 7.74 (d, J = 2.0 Hz, 1H), 7.28 (tt, J = 13.1, 6.8 Hz, 6H), 7.20 (d, J = 3.1 Hz, 1H),7.15 (dd, J = 8.6, 2.0 Hz, 1H), 6.37 (d, J = 3.1 Hz, 1H), 3.60 (d, J = 14.9 Hz, 2H), 3.26 (d, J = 5.0 Hz, 1H),3.08-3.01 (m, 3H), 2.39 (d, J = 7.0 Hz, 2H), 2.21-2.13 (m, 1H), 2.04 (d, J = 15.4 Hz, 2H), 1.74-1.60 (m,2H), 1.27 (s, 2H). 13C NMR (151 MHz, CD3OD) delta 170.66, 136.38, 133.81, 129.79, 128.59, 128.42, 127.97,126.86, 125.29, 115.83, 115.76, 112.47, 110.75, 101.07, 72.24, 70.09, 60.80, 57.69, 53.42, 52.37, 41.90,31.68, 31.23, 29.38, 28.89, 22.34, 13.05. HRMS (ESI): calcd. For C23H27N3O [M + H]+ 362.2227, found362.2242.

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

Reference:
Article; Guo, Yan; Yang, Hongyu; Huang, Zhongwei; Tian, Sen; Li, Qihang; Du, Chenxi; Chen, Tingkai; Liu, Yang; Sun, Haopeng; Liu, Zongliang; Molecules; vol. 25; 3; (2020);,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 157590-59-5, 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. 157590-59-5 name is 4-Chloro-5-(trifluoromethyl)benzene-1,2-diamine, 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: Synthesis of 4-[6-chloro-5-(trifluoromethyl)-lH-l,3-benzodiazol-2- yl]butan-l-ol [0593] 4-chloro-5-(trifluoromethyl)benzene-l,2-diamine (5.00 g, 23.74 mmol) was dissolved in HC1 solution (4 M solution) (18.85 ml) at r.t. and delta-valerolactone (2.62g,26.12 mmol) was added slowly. The reaction was heated to 135 C for 2 hrs then slowly cooled to r.t. The reaction was quenched by the addition of sat. NaHC03 solution (200 ml) to pH 8. The mixture was extracted with EtOAc (3 x 150 ml) and the combined organic layers were dried over Na2S04, filtered and concentrated in vacuo to give the crude product as a brown solid which was triturated with ether (100 ml) to give the pure product (5.88 g,84%): MS (ESI+) for Ci2Hi2ClF3N20 m/z 293.4 [M+H]+; LC purity 90% (ret. time, 1.49 min); 1H NMR (250 MHz, CHLOROFORM-d) delta ppm 1.39 – 1.72 (2 H, m), 1.71 – 1.94 (2H, m), 2.87 (2 H, t, 7=7.61 Hz), 3.58 (2 H, t, 7=6.09 Hz), 7.42 – 7.96 (2H, m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Chloro-5-(trifluoromethyl)benzene-1,2-diamine, and friends who are interested can also refer to it.

Reference:
Patent; EPIZYME, INC.; OLHAVA, Edward James; CHESWORTH, Richard; KUNTZ, Kevin, Wayne; WO2012/75492; (2012); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 873-38-1, 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. 873-38-1, name is 2-Bromo-4-chloroaniline, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 2-bromo-4-chloroaniline (1 g, 4.84 mmol) in acetic anhydride (5 ml, 4.84 mmol) was stirred at RT for 1.5 hrs. The resulting suspension was collected by filtration and dried on a vacuum line to give the title compound as a white solid. (0532) LC-MS: Rt 0.90 mins; MS m/z 250.0 [M+H]+; Method 2minLowpH (0533) 1H NMR (400 MHz, DMSO-d6) delta 9.51 (1H, s), 7.78 (1H, d), 7.62 (1H, d), 7.44 (1H, dd), 2.08 (3H, s).

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-4-chloroaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS AG; EDWARDS, Anne-Marie; AHMED, Mahbub; PULZ, Robert Alexander; ROONEY, Lisa Ann; SMITH, Nichola; TROXLER, Thomas Josef; (31 pag.)US2015/329549; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1020198-58-6, name is 2-Bromo-1-chloro-3,5-difluorobenzene, belongs to chlorides-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 1020198-58-6, Formula: C6H2BrClF2

A mixture of 2-bromo-1-chloro-3,5-difluorobenzene (800 mg), bis(pinacolato)diborone (1.1 g), bis(triphenylphosphine)palladium chloride (123 mg), triphenylphosphine (92 mg), potassium acetate (1.0 g), and 1,4-dioxane (24 mL) was heated under stirring in an oil bath at 100 C. for 18 hours. The reaction mixture was returned to room temperature, the insoluble materials were separated by filtration, and the filtrate was concentrated under reduced pressure. The resulting residue was purified under silica gel column chromatography (hexane/ethyl acetate) to obtain 2-(2-chloro-4,6-difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (242 mg).

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; Kinoyama, Isao; Miyazaki, Takehiro; Koganemaru, Yohei; Washio, Takuya; Hamaguchi, Wataru; US2012/142727; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 13918-92-8, 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 13918-92-8 as follows.

To a solution of 5-bromo-2-methoxypyridin-3-amine (10.15 g, 50 mmol) in pyridine (50 mL) was added 2,4-difluorobenzene-1-sulfonyl chloride (11.68 g, 60 mol) slowly at 0 C. The mixture was stirred at rt for 19 hours and concentrated in vacuo. The residue was dissolved in MeOH (100 mL) and NaOH (2.50 g, 60 mmol). The resulted mixture was stirred at rt for 12 hours and concentrated in vacuo. The residue was dissolved in H2O (50 mL) and the resulted mixture was extracted with DCM (100 mL¡Á3). The combined organic phases were washed with brine (100 mL¡Á3), dried over anhydrous Na2SO4, and concentrated in vacuo to give the title compound as a brown solid (16.90 g, 89.1%). [0304] MS (ESI, pos. ion) m/z: 379.0 [M+H]+.

According to the analysis of related databases, 13918-92-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; Xi, Ning; US2014/234254; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 63624-28-2, 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 63624-28-2 as follows.

0.5 g of 60% sodium hydride in oil is added to a mixture of 3.6 g of 5-chloro-1H-indole-2,3-dione in 20 ml of DMF, and the mixture is stirred for 30 minutes at 20 C. 4.8 g of 2,4-dimethoxybenzenesulphonyl chloride are then added and the mixture is stirred at 20 C. for 1 hour. The resulting mixture is concentrated under vacuum (1.3 Pa), the residue is extracted with EtOAc, the organic phase is washed with water and dried over Na2SO4, and the solvent is evaporated off under vacuum. The residue is triturated in iso ether and the precipitate formed is filtered off by suction. 2.9 g of the expected product are obtained after crystallization from hot EtOAc, m.p.=194.5 C.

According to the analysis of related databases, 63624-28-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Di Malta, Alain; Garcia, Georges; Roux, Richard; Schoentjes, Bruno; Serradeil-Le Gal, Claudine; Tonnerre, Bernard; Wagnon, Jean; US2004/180878; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 174913-12-3, 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. 174913-12-3, name is 1-Bromo-3-chloro-5-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

Preparation 17 1-Bromo-2,3-dichloro-5-methoxybenzene 1-Bromo-3-chloro-5-methoxybenzene (Preparation 16, 6.0 g, 27 mmol) and trichloroisocyanuric acid (2.3 g, 9.9 mmol) were stirred in dimethylformamide (100 ml) at 50 C. for 3 hours. n-Heptane was added and the mixture filtered to remove insoluble impurities. The mixture was then concentrated in vacuo and the residue purified by silica gel column chromatography, eluding with n-heptane:ethyl acetate 9:1, to afford the title product as a white solid (5.0 g). 1H-NMR (CDCl3): 3.80 (s, 3H), 7.00 (s, 1H), 7.20 (s, 1H). GC-MS m/z 256 [MH]+, Rt=4.60 min

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-3-chloro-5-methoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Pfizer Limited; US2007/105872; (2007); A1;,
Chloride – Wikipedia,
Chlorides – 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. 89794-02-5, name is 4-Bromo-2-chlorotoluene, This compound has unique chemical properties. The synthetic route is as follows., Safety of 4-Bromo-2-chlorotoluene

Example 3 Bis(4,4′-(3-chloro-4-methylphenylhydroxyboryl)benzyl) ether; [Show Image] Bis(4-bromobenzyl) ether (157 mg) was dissolved in 8 mL of ether, and the solution was cooled to -78C. After addition of 2 mL of a 1 M sec-BuLi solution, the mixture was stirred for two hours (solution A). 4-Bromo-2-chlorotoluene (205 mg) was dissolved in 8 mL of ether, and the solution was cooled to -90C. After addition of 2 mL of a 1 M sec-BuLi solution, the mixture was stirred for two hours. Triisopropoxyborane (0.46 mL) was added to the resulting solution, and the mixture was stirred for 1.5 hours. The solution A was added to the solution, and the mixture was gradually returned to room temperature and stirred overnight. Aqueous dilute hydrochloric acid was added, and the mixture was stirred. The organic layer was dried and then concentrated and applied to a silica gel column to give 77 mg of the entitled compound as a grease. Rf= 0.48 (EtOAc, Hexane 1: 1) NMR (CDCl3) 2.35 (s, 6H), 4.53 (s, 4H), 7.1-8.2 (m, 14H)

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 89794-02-5.

Reference:
Patent; Japan Science and Technology Agency; EP1961756; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics