Tag: M.W=200-300

Application of 14862-52-3, 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. 14862-52-3, name is 3,5-Dibromochlorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of 1,3-dibromo-5-chlorobenzene (800 mg, 2.96 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (600 mg, 2.96 mmol) in 1,4-dioaxane (15 mL) K2CO3 (1.2 g, 8.80 mmol) was added and the mixture was degassed with argon for 20 minutes. Pd (PPh3)4 (102 mg, 0.08 mmol) was added to reaction mixture and degassed for another 20 minutes. The reaction mixture was refluxed under stirring for 8 hours and then filtered through celite pad. The filtrate was concentrated and the residue was purified by column chromatography on silica (100-200 mesh) eluting with 15% ethyl acetate in petroleum ether to afford the title compound as white solid (400 mg, 50 %). 1H NMR: (300 MHz, CDCl3) delta 8.70 (dd, J = 4.5, 1.5 Hz, 2H), 7.65-7.64 (m, 1H), 7.59-7.58 (m, 1H), 7.54-7.53 (m, 1H), 7.45 (dd, J = 4.2, 1.5 Hz, 2H); ESIMS: m/z = 268.0 [(M+H)+].

The synthetic route of 3,5-Dibromochlorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Blass, Benjamin E.; Iyer, Pravin; Abou-Gharbia, Magid; Childers, Wayne E.; Gordon, John C.; Ramanjulu, Mercy; Morton, George; Arumugam, Premkumar; Boruwa, Joshodeep; Ellingboe, John; Mitra, Sayan; Reddy Nimmareddy, Rajashekar; Paliwal, Shalini; Rajasekhar, Jamallamudi; Shivakumar, Savithiri; Srivastava, Pratima; Tangirala, Raghuram S.; Venkataramanaiah, Konda; Bobbala, Ramreddy; Yanamandra, Mahesh; Krishnakanth Reddy; Bioorganic and Medicinal Chemistry Letters; vol. 28; 13; (2018); p. 2270 – 2274;,
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Application of 873-38-1,Some common heterocyclic compound, 873-38-1, name is 2-Bromo-4-chloroaniline, molecular formula is C6H5BrClN, 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 a 20 mL microwave vial was added 2-bromo-4-chloroaniline (3 g, 14.53mmol), 4,4,5,5 -tetramethyl-2-(tetramethyl-1 ,3,2-dioxaborolan-2-yl)- 1 ,3,2-dioxaborolane(5.53 g, 21.80 mmol), KOAc (3.66 g, 37.3 mmol), Pd(dppf)C12-CH2C12 adduct (0.32 g, 0.44 mmol) and DMSO (9 mL). The resulting suspension was purged with N2, capped and heated at 80 C for 22 h. The reaction was cooled to rt. Water was added to dissolve the salts, then the reaction was filtered. The remaining solid was suspended in DCM andthe insoluble solid was filtered. The filtrate was concentrated and then purified by normalphase chromatography to give 4-chloro-2-(tetramethyl- 1 ,3,2-dioxaborolan- 2-yl)aniline(3.15 g, 86 % yield) as a white solid. MS (ESI) m/z: 172.3 (M-C6H1o+H). ?H NMR(400MHz, CDC13) 7.54 (d, J=2.6 Hz, 1H), 7.13 (dd, J=8.8, 2.6 Hz, 1H), 6.52 (d, J=8.6Hz, 1H), 4.72 (br. s., 2H), 1.34 (s, 12H).

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PABBISETTY, Kumar Balashanmuga; CORTE, James R.; DILGER, Andrew K.; EWING, William R.; ZHU, Yeheng; (178 pag.)WO2017/19819; (2017); A1;,
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Synthetic Route of 928782-97-2, 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. 928782-97-2 name is 4-Chloro-2-(phenylethynyl)aniline, 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: To a microwave vial, a mixture of 2-alkynylaniline (1 equiv), sulfonyl hydrazide (1.5 equiv), I2 (10 mol%) and pTSA (50 mol%) was taken in 1,4-dioxane irradiated for 15 min at 110C, 100W in CEM microwave synthesizer. The progress and completion of reaction is monitored by TLC using EtOAc/n-Hexane (1:10) as an eluent. The reaction mixture was then cooled to room temperature and extracted with ethyl acetate. The combined organic phase was washed with sodium thiosulphate (50 mL) and dried over Na2SO4. After filtration and evaporation of the solvents in vacuum, the mixture of products was separated by column chromatography on silica gel (EtOAc/n-hexane: 1:10) to yield the desired product 3.

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

Reference:
Article; Sharma, Shivani; Pathare, Ramdas S.; Sukanya; Maurya, Antim K.; Goswami, Bhagyashree; Agnihotri, Vijai K.; Sawant, Devesh M.; Pardasani, Ram T.; Tetrahedron Letters; vol. 58; 40; (2017); p. 3823 – 3826;,
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Electric Literature of 1127-85-1, 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. 1127-85-1 name is 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline, 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: To the solution of compounds 22 (0.3 g, 1.5 mmol) in DMF wereadded K2CO3 (1.95 mmol) and 4-amino-1-Boc-piperidine (2.7 mmol). The reaction was stirred at 80 C for 8 h. Then the mixture was extractedwith ethyl acetate, washed with brine, dried over MgSO4, andevaporated. The residue was purified by column chromatography togive the product (0.5 g, 92% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline, and friends who are interested can also refer to it.

Reference:
Article; Fang, Yuanying; Xiong, Lijuan; Hu, Jianguo; Zhang, Shaokun; Xie, Saisai; Tu, Liangxing; Wan, Yang; Jin, Yi; Li, Xiang; Hu, Shaojie; Yang, Zunhua; Bioorganic Chemistry; vol. 86; (2019); p. 103 – 111;,
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Application of 41965-95-1, 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. 41965-95-1, name is 3-Chloro-4-methoxybenzylamine Hydrochloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(3-Chloro-4-methoxyphenyl) methanamine hydrochloride compound of formula-6a (76.98 g) was added to the organic layer containing ethyl 4-chloro-2-(methylthio) pyrimidine-5-carboxylate compound of formula-5, which is obtained in step-b). Water (100 ml), followed by sodium carbonate (110.3 g) were added to the reaction mixture at 25-30C and stirred for 4 hours at the same temperature. After completion of the reaction, water was added to it. Both the organic and aqueous layers were separated; the aqueous layer was extracted with toluene. All the organic layers were combined and washed with water. Distilled off the solvent from the organic layer under reduced pressure. The reaction mixture was cooled to 30-35C. 700 ml of cyclohexane: ethyl acetate (in 9.5:5 ratio) was added to the reaction mixture. The reaction mixture was heated to 70-75C and stirred until complete dissolution. The reaction mixture was cooled to 10-15C and stirred for 3 hours. Filtered the precipitated solid, washed with cyclohexane and then dried to get title compound.Yield: 90 gms; Melting range: 81 -84C; Purity by HPLC: 95.3%.

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-Chloro-4-methoxybenzylamine Hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MSN LABORATORIES PRIVATE LIMITED; THIRUMALAI RAJAN, Srinivasan; ESWARAIAH, Sajja; SATYANARAYANA, Komati; WO2015/1567; (2015); A1;,
Chloride – Wikipedia,
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928782-97-2, name is 4-Chloro-2-(phenylethynyl)aniline, belongs to chlorides-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. name: 4-Chloro-2-(phenylethynyl)aniline

A mixture of 2-alkynylaniline 1a-1e (0.2 mmol), dichalcogenide 2a-2e (0.15 mmol), CuI (0.02 mmol), and Cs2CO3 (0.2 mmol) in DMSO (2 mL) was stirred at 80 C under an air atmosphere. After completion of the reaction that was monitored by GC-MS or TLC, 25 mL water was added, and the mixture was extracted with ethyl acetate, the combined organic layers were washed with water (10 mL x 3), dried over anhydrous Na2SO4. After filtration and removal of solvents in vacuum, the residue was purified by silica gel column chromatography to afford the corresponding products.

The synthetic route of 928782-97-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Zhen; Hong, Longcheng; Liu, Ruiting; Shen, Jianzhong; Zhou, Xigeng; Tetrahedron Letters; vol. 52; 12; (2011); p. 1343 – 1347;,
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Related Products of 6579-54-0,Some common heterocyclic compound, 6579-54-0, name is 2,6-Dichlorobenzenesulfonyl chloride, molecular formula is C6H3Cl3O2S, 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.

3. Preparation of N-(5,7-dimethoxy[1,2,4]triazolo-[1,5-a]pyrimidin-2-yl)-2,6-dichlorobenzene-sulfonamide (Compound 1) 2-Amino-5,7-dimethoxy[1,2,4]triazolo[1,5-a]-pyrimidine (0.75 g, 3.8 mmol) and 2,6-dichlorobenzene-sulfonyl chloride (1.86 g, 7.6 mmol) were mixed in dry acetonitrile (15 mL). To this mixture was added dry pyridine (0.61 mL) and dry DMSO (54 muL, 0.7 mmol). The mixture was allowed to stir at room temperature. After 24 hours, the solvent was removed in vacuo, the residue was partitioned between CH2Cl2 (300 mL) and 2N HCl and the solids were collected by vacuum filtration to give a white solid A. The CH2Cl2 was dried (MgSO4) and removed in vacuo to give a white solid B. Both HPLC and NMR indicated that solid A and B are product. The solids were combined to afford the product as a white powder (1.41 g, 92%). mp 211-213 C. Anal: Cacld for C13H11Cl2N5O4S: C, 38.63; H, 2.74; N, 17.33; S, 7.93; found: C, 38.11; H, 2.68; N, 16.83; S, 7.77. 1H NMR (DMSO-d6): delta 12.4 (bs, 1H); 7.64-7.54 (m, 3H); 6.26 (s, 1H); 4.07 (s, 3H); 3.88 (s, 3H).

The synthetic route of 6579-54-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Johnson, Timothy Calvin; VanHeertun, John Cord; Ouse, David George; Arndt, Kim Eric; Pobanz, Mark Ardrew; Walker, David Keith; US2002/111361; (2002); 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. 19752-55-7, name is 1-Bromo-3,5-dichlorobenzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-Bromo-3,5-dichlorobenzene

Under a nitrogen atmosphere, tert-butyllithium (1.3 Msolution in Pentane, 17.8 mL, 23.2 mmol) was added dropwise to a solution of 3,5-dichlorobromobenzene (5.0 g,22.1 mmol) in tetrahydrofuran (50 mL) dropwise over 30 min. The mixture was stirred for 2 hours and then N-methoxy-N-Methyl-2,2,2-trifluoroacetamide (3.64 g, 23.2 mmol) was added dropwise to the mixed solution, the reaction 2 was stirred while maintaining -78 ° Chour. Remove the low temperature, the temperature gradually rose to room temperature, the reaction was maintained at room temperature for 8 hours. Saturated ammonium chloride solution (50 mL)The reaction was quenched and extracted with ether (20 mL & apos; 3). The organic phases were combined and washed with brine (20 mL & apos; 2)The phases were dried over anhydrous magnesium sulfate, filtered, the solvent was removed and the residue was distilled under reduced pressure to give a colorless transparent liquid 1 (1.56 g). Yield29percent.

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

Reference:
Patent; Jingmen Pharmaceutical Industry Technology Institute; Wang Yong; Li Liwei; Hu Jianmei; Gu Dongyun; Huang Daoyou; (12 pag.)CN107353189; (2017); A;,
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Synthetic Route of 60811-21-4, A common heterocyclic compound, 60811-21-4, name is 4-Bromo-2-chloro-1-fluorobenzene, molecular formula is C6H3BrClF, 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 76 5′-(3-Chloro-4fluorophenyl)-spiro [cyclopentane-1,3′-[3H]indol]-2′(1’H)-one A solution of 3-chloro-4-fluoro-bromobenzene (0.4 cm3, 0.66 g, 3.1 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.2 g) in ethylene glycol dimethyl ether (20 cm3) was stirred under N2 for 20 minutes. To this mixture was then added (spiro[cyclopentane-1,3′-[3H]indol]-2′(1’H)-one-5-yl)boronic acid (1.0 g, 4.7 mmol) and sodium carbonate (1.0 g, 9.4 mmol) in water (5 cm3). The solution was brought to reflux for 18 hours and then cooled to room temperature, poured into 2N NaOH and extracted with EtOAc (*3). The combined extracts were washed with water, brine, dried (MgSO4), and evaporated. The residue was purified by column chromatography (SiO2, EtOAc, hexane) to afford the title compound (0.65 g, 66%) as a pale-yellow solid. mp: 202-204 C., 1H NMR (DMSO-d6) delta 10.4 (s, 1H), 7.9 (dd, 1H, J=2.3, 4.9 Hz), 7.7-7.6 (m, 1H), 7.6 (d, 1H, J=1.5 Hz), 7.5 (s, 1H), 7.4 (d, 1H, J=1.8 Hz), 6.9 (d, 1H, J=8.0 Hz), 2.0-1.9 (m, 8H); MS [M-H]-=314.

The synthetic route of 60811-21-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wyeth; Ligand Pharmaceuticals, Inc.; US6462032; (2002); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 63624-28-2, These common heterocyclic compound, 63624-28-2, name is 2,4-Dimethoxybenzene-1-sulfonyl chloride, 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.

D) (2S, 4R)-1-[5-Chloro-1-(2,4-dimethoxyphenylsulfonyl)-3-(2,4-dimethoxypyrimidin-5-yl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-4-hydroxypyrrolidine-2-carboxylic acid dimethylamide Sodium hydride (12 mg of 60% dispersion in mineral oil, 0.3 mmol) was added to an ice-cold solution of the mixture of diastereomers from step C (139 mg, 0.30 mmol) in DMF (1.5 ml). The reaction mixture was stirred at 0 C. for 0.5 h and then 2,4-dimethoxyphenylsulfonyl chloride (71 mg, 0.3 mmol) was added. After the reaction mixture had been stirred at room temperature for one hour, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over magnesium sulfate. Purification by chromatography (silica gel, 5% MeOH in dichloromethane) resulted in 63 mg of the less polar diastereomer ((-) isomer) and 25 mg of the more polar diastereomer ((+) isomer) as colorless waxes.

The synthetic route of 63624-28-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Abbott GmbH & Co. KG; US2005/70718; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics