Month: September 2021

Electric Literature of 13726-14-2, 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. 13726-14-2, name is 4-Chloro-3-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: N-Benzylpiperidone (1 g, 5.2 mmol, 1 equiv), 3, 4 difluoroaniline (0.52 mL, 5.2 mmol, 1 equiv) and sodium sulfate (3.7 g, 26.4 mmol, 5 equiv) were suspended in dichloromethane (20 mL). Sodium triacetoxyborohydride (1.3 g, 6.33 mmol, 1.2 equiv) was added and the reaction mixture was stirred at room temperature overnight. Aqueous sodium hydrogen carbonate was added followed by stirring for 30 min. The reaction mixture was extracted with dichloromethane and the combined organic phases were washed with brine, dried over sodium sulfate, filtrated and concentrated in vacuo. The residue obtained upon evaporation of solvent was chromatographed over silica gel and eluted with 35% ethyl acetate/hexane to give the 26 as a light yellow colored solid (1.2 g, 75% yield).

The chemical industry reduces the impact on the environment during synthesis 4-Chloro-3-methoxyaniline. I believe this compound will play a more active role in future production and life.

Reference:
Article; Deekonda, Srinivas; Wugalter, Lauren; Kulkarni, Vinod; Rankin, David; Largent-Milnes, Tally M.; Davis, Peg; Bassirirad, Neemah M.; Lai, Josephine; Vanderah, Todd W.; Porreca, Frank; Hruby, Victor J.; Bioorganic and Medicinal Chemistry; vol. 23; 18; (2015); p. 6185 – 6194;,
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Reference of 93-50-5,Some common heterocyclic compound, 93-50-5, name is 4-Chloro-2-methoxyaniline, molecular formula is C7H8ClNO, 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.

Preparation 38; 3-Biphenyl-4-yl-4-(4-chloro-2-methochiyphenyl)-5-methyl-4/-/-1 ,2,4-triazole; A mixture of 2-biphenyl-4-yl-5-methyl-1 ,3,4-oxadiazole [(1g, 4.2mmol), Bioorganic & Medicinal Chemistry, 2002, 10, 1905], the product of preparation 37 (800mg, 5.04mmol) and para-toluenesulfonic acid (200mg) in xylene (2OmL) was heated at 15O0C for 10 hours. Further para-toluenesulfonic acid (100mg) was added at regular intervals, until all of the starting material was consumed. After heating at 15O0C for 4.5 hours, the reaction mixture was diluted with 2M hydrochloric acid, extracted with ethyl acetate and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with EPO dichloromethane:methanol:0.88 ammonia, 98:2:0.2. The appropriate fractions were evaporated under reduced pressure and the residue was triturated with ethyl acetate (x3) to afford the title compound as a pale brown solid in 51% yield, 860mg.1HNMR(400MHz, CDCI3) delta: 2.30(s, 3H), 3.74(s, 3H), 7.04-7.10(m, 3H), 7.32-7.57(m, 9H); LRMS APCI m/z 376 [M+H]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Chloro-2-methoxyaniline, its application will become more common.

Reference:
Patent; PFIZER LIMITED; WO2006/100588; (2006); A1;,
Chloride – Wikipedia,
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Reference of 60811-21-4, These common heterocyclic compound, 60811-21-4, name is 4-Bromo-2-chloro-1-fluorobenzene, 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.

4-Bromo-2-chloro-1-fluorobenzene (720 mmol, 150.8 g), phenylboronic acid (792 mmol, 96.6 g), 2 M aqueous solution (360 ml) of potassium carbonate (1,080 mmol, 149.3 g), toluene (720 ml), and ethanol (144 ml) were added to a three-necked flask, and the flask was flushed with nitrogen. Tetrakis(triphenylphosphine) palladium(0) (Pd(PPh3)4(21.6 mmol, 21.6 g) was added thereto, and the reaction mixture was heated under stirring at a temperature 80 C. for 8 hours. The reaction mixture was cooled to room temperature, diluted with toluene (1 L), filtered by using celite, and washed twice with water by using a separatory funnel. The reaction mixture was dried by using anhydrous magnesium sulfate, filtered through a silica gel pad, and then, concentrated. The precipitated solid was purified by silica gel column chromatography (developing solvent hexane_toluene=7:3) and recrystallized in methanol to obtain Intermediate 3-1. The amount of Intermediate 3-1 obtained was 101.2 g and the yield of Intermediate 3-1 was 68%.

Statistics shows that 4-Bromo-2-chloro-1-fluorobenzene is playing an increasingly important role. we look forward to future research findings about 60811-21-4.

Reference:
Patent; Samsung Electronics Co., Ltd.; INAYAMA, Satoshi; IRISA, Shiro; KORAI, Keisuke; SAKURAI, Rie; ITO, Mitsunori; NUMATA, Masaki; (265 pag.)US2019/214570; (2019); A1;,
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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. 7149-75-9, name is 4-Chloro-3-methylaniline, A new synthetic method of this compound is introduced below., SDS of cas: 7149-75-9

General procedure: Oxo ester 11-15 (10 mmol) was dissolved in THF(50 ml). Solution of LiOH·H2O (15 mmol) in 20 ml of water was addeddropwise at 5-10 C. After stirring at room temperature (3-8 h, TLCcontrol) the mixture was concentrated to approximately quarter of volume,diluted with 50 ml of water and washed with Et2O (3×30 ml). The waterlayer was acidified with 5% H2SO4 to pH 5, the product was extracted withEt2O (3×30 ml), dried over Na2SO4 and concentrated in vacuo. The crudeoxo acids were unstable and were immediately processed further. Primaryamine (0.55 mmol) and oxo acid (0.50 mmol) were dissolved in EtOH(3.0 ml). Isocyanide (0.55 mmol) was added and the reaction mixture wasstirred at 60-65 C for 12 h, then evaporated in vacuo. The residue was dissolvedin EtOAc (3 ml) and treated with 5 ml of saturated aqueous NaHCO3,the organic layer was separated, the aqueous one was extracted with EtOAc(2×2 ml). The combined organic extracts were washed with water (2×5 ml),dried over Na2SO4 and concentrated in vacuo. The residue was treated with10% EtOAc in Et2O (to cause crystallization of the product), or purifiedby chromatography (silica gel, EtOAc-hexane, 1 : 20 1 : 10). For characteristicsof the products, see Online Supplementary Materials.

The synthetic route of 7149-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Stolyarenko, Vasiliy Yu.; Evdokimov, Anatoliy A.; Shishkin, Vladimir I.; Mendeleev Communications; vol. 23; 4; (2013); p. 233 – 234;,
Chloride – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 60811-21-4, name is 4-Bromo-2-chloro-1-fluorobenzene, 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 60811-21-4, name: 4-Bromo-2-chloro-1-fluorobenzene

To a solution of 4-bromo-2-chloro-1-fluorobenzene (5.00 g, 23.9 mmol) in THF (40 mL) was added lithium diisopropylamide (14.3 mL, 28.6 mmol) drop wise at -78 C. The resultant mixture was stirred at -78 C. for 2 h and then DMF (2.70 mL, 35.8 mmol) was added. The reaction mixture was warmed to room temperature, quenched with aq. NH4Cl, and extracted with EtOAc (3*100 mL). The combined organic layers were concentrated and purified by chromatography (0-10% EtOAc in petroleum ether) to give the title compound. 1H NMR (400 MHz, CDCl3) delta 10.27-10.33 (m, 1H), 7.56 (dd, J=8.6 Hz, 4.3 Hz, 1H), 7.18-7.26 (m, 1H).

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; Merck Sharp & Dohme Corp.; Lapointe, Blair T.; Fuller, Peter H.; Gunaydin, Hakan; Liu, Kun; Molinari, Danielle F.; Pu, Qinglin; Scott, Mark E.; Trotter, B. Wesley; Zhang, Hongjun; US2018/305320; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 38762-41-3, The chemical industry reduces the impact on the environment during synthesis 38762-41-3, name is 4-Bromo-2-chloroaniline, I believe this compound will play a more active role in future production and life.

4-bromo-2-chloroaniline (5 g, 24.2 mmol), cyclopropylboronic acid (4 g, 48.4 mmol), tricyclohexylphosphine (680 mg, 2.42 mmol), palladium acetate (271 mg, 1.21 mmol)and potassium carbonate (15.4 g, 72.6 mmol)were added to 130 mL of a mixture of toluene and water (V:V=25:1). The mixture was heated to 100C and stirred for 12 hours. The reaction solution was filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography with elution system B to obtain the title compound 24a (2.5 g, yield 61.7%)as a yellow liquid. MS m/z (ESI): 168.1 [M+1]

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

Reference:
Patent; Jiangsu Hengrui Medicine Co. Ltd.; Shanghai Hengrui Pharmaceutical Co. Ltd.; YANG, Fanglong; ZHANG, Ling; WANG, Chunfei; HE, Mingxun; HU, Qiyue; HE, Feng; TAO, Weikang; SUN, Piaoyang; (101 pag.)EP3395809; (2018); 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. 367-22-6, name is 4-Chloro-3-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 367-22-6

Step 12: Preparation for N-(4-Chloro-3-fluorophenyl)-5-(tetrahydrofuran-3-yloxy)-2,3-dihydro-[1,4]dioxino[2,3-f]quinazolin-10-amine To a solution of 10-chloro-5-(tetrahydrofuran-3-yloxy)-2,3-dihydro-[1,4]dioxino[2,3-f]quinazoline (0.1 g, 0.3 mmol) in isopropanol (3 mL) was added 4-chloro-3-flouroaniline (0.06 g, 0.4 mmol). The solution was stirred at 80 C. for 4 hours. After cooling to ambient temperature, the solution was concentrated to obtain a yellow solid which was purified by column chromatography on silicon gel (dichloromethane:methanol=100:1) to obtain a yellow solid (0.09 g, yield=62%). 1H NMR (DMSO-d6, 400 MHz): delta 10.45 (s, 1H), 8.73 (s, 1H), 7.97-7.94 (m, 1H), 7.66-7.65 (m, 1H), 7.54 (t, 1H, J=8.9 Hz), 7.14 (s, 1H), 5.20-5.18 (m, 1H), 4.61-4.59 (m, 2H), 4.45-4.44 (m, 2H), 3.96-3.88 (m, 3H), 3.81-3.79 (m, 1H), 2.37-2.34 (m, 1H), 2.08-2.06 (m, 1H). MS: 418(M+H+).

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 367-22-6.

Reference:
Patent; BEIJING SCITECH-MQ PHARMACEUTICALS LIMITED; SHENG, Wang; YANG, Leifu; PAN, Zhiyong; (46 pag.)US2017/355683; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 39065-95-7,Some common heterocyclic compound, 39065-95-7, name is 4-(Chlorodifluoromethoxy)aniline, molecular formula is C7H6ClF2NO, 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 (1R,4R)-9-bromo-4-hydroxy-1-methyl-1,2,3,4-tetrahydrobenzo[4,5]imidazo [1,2-a]pyridine-7-carboxylic acid (49h, 10 mg, 0.031 mmol), 4-[chloro(difluoro)methoxy]aniline (1h, 7.14 mg, 0.037 mmol) in DMF (1 mL) was added HATU (14.03 mg, 0.037 mmol) and DIEA (11.92 mg, 0.092 mmol, 16.07 uL). The mixture was stirred at 15 C. for 5 hr. LCMS showed desired ms was detected. TLC (ethyl acetate_methanol=10:1, Rf=0.40) showed a new spot was formed. The reaction mixture was concentrated under reduced pressure to remove solvent. The residue was diluted with H2O (10 mL) and extracted with EtAOc (10 mL*3). The combined organic layers were washed with brine, dried over Ns2SO4, filtered and concentrated under reduced pressure to give a residue. The residue was purified by prep-TLC (SiO2, ethyl acetate_methanol=10:1) to give 49i as a white solid. 1H NMR (400 MHz, CDCl3-d) delta 8.09 (d, J=1.3 Hz, 1H), 8.00 (d, J=1.3 Hz, 1H), 7.71 (d, J=8.9 Hz, 2H), 7.25 (s, 1H), 5.46 (br t, J=5.8 Hz, 1H), 5.18 (br s, 1H), 2.76-2.60 (m, 1H), 2.39-2.17 (m, 2H), 1.96-1.86 (m, 1H), 1.53 (d, J=6.6 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(Chlorodifluoromethoxy)aniline, its application will become more common.

Reference:
Patent; Terns, Inc.; ROMERO, F. Anthony; KIRSCHBERG, Thorsten A.; HALCOMB, Randall; XU, Yingzi; (144 pag.)US2020/87283; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 19752-55-7, A common heterocyclic compound, 19752-55-7, name is 1-Bromo-3,5-dichlorobenzene, molecular formula is C6H3BrCl2, 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.

In Nitrogen environment I-16(99 g, 208 mmol) was dissolved in in 600 mL tetrahydrofuran (THF), where the 1-bromo-3,5-dichlorobenzene(56.4 g, 250 mmol) and tetrakis( triphenylphosphine) palladium was stirred into the (2.40 g, 2.08 mmol) into a saturated potassium carbonate in water (71.9 g, 520 mmol) was heated to reflux at 80 ° C for 8 hours. After the reaction was completed, the reaction solution into water and extracted with dichloromethane (DCM) and then water was removed with anhydrous MgSO4, filter and was concentrated under reduced pressure. Thus the resulting residue was separated and purified by flash column chromatography to obtain the compound I-17(53.7 g, 79percent).

The synthetic route of 19752-55-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cheil Industries Co., Ltd; Lee, Han Ir; Yu, Uhn Sun; Kang, Dong Min; Kang, Uii Soo; Yang, Yong Tak; Oh, Jae Jin; Yu, Dong Gyu; Lee, Sang Sin; Jang, Yuna; Jung, Su Young; Han, Su Jin; Hong, Jin Suk; (59 pag.)KR2015/6758; (2015); A;,
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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. 15205-11-5, name is 2-Chloro-4-fluorobenzylamine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 15205-11-5

General procedure: To a solution of acid 3 (0.384g, 1mmol), HATU (0.38g, 1mmol), and Et3N (1mL) in 20mL of dry CH2Cl2 was added an equimolar amount of the appropriate amine. The mixture was kept stirring at room temperature for 24h. After TLC detection to show no starting materials, the mixture was extracted with 100mL ethyl acetate and washed with saturated NaHCO3 (3×30mL) and saturated NaCl (1×50mL). The organic layers were dried over MgSO4 and evaporated under vacuum. The crude product was purified by column chromatography with methanol: CH2Cl2=1: 30 to obtain intermediates 4a-4u.

The synthetic route of 15205-11-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ju, Han; Zhang, Jian; Sun, Zhuosen; Huang, Zheng; Qi, Wenbao; Huang, Bing; Zhan, Peng; Liu, Xinyong; European Journal of Medicinal Chemistry; vol. 146; (2018); p. 220 – 231;,
Chloride – Wikipedia,
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