Tag: M.W=200-300

Electric Literature of 6579-54-0, 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. 6579-54-0 name is 2,6-Dichlorobenzenesulfonyl chloride, 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: A solution of the appropriate acid halide fragments (4.8 mmol)in dry pyridine (5 mL) was dropwise added to a well-stirredmixture of the intermediate 3-amino-substituted rutaecarpine 5(4 mmol) in dry pyridine (50 mL) at room temperature. The reactionwasstirred for 30 min and monitored by TLC. After the reactioncompleted, the pH was adjusted to neutral with dilute hydrochloricacid. The pyridine and residual sulfonyl chloride were distilledunder reduced pressure. The mixture was extracted with an ethylacetate-water system. The aqueous layer was discarded and ethyl acetate was evaporated to obtain crude product. The crude productwas washed with water and dried under vacuum. The solid residuewas purified by flash chromatography on silica gel with ethyl acetate/petroleum ether (1:1) elution to provide the desired derivatives6a-6p, 7a-7c, and 8a.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,6-Dichlorobenzenesulfonyl chloride, and friends who are interested can also refer to it.

Reference:
Article; Wu, Mingfei; Ma, Jie; Ji, Lijun; Wang, Min; Han, Jianfei; Li, Zeng; European Journal of Medicinal Chemistry; vol. 177; (2019); p. 198 – 211;,
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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. 202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3-Chloro-4-((3-fluorobenzyl)oxy)aniline

(iii) Preparation of N-[3-chIoro-4-[(3-fluorobenzyIoxy)phenyl]-6-iodo- quinazolin amine (3) Into a one liter four-necked round bottomed flask, 500mL of acetic acid, 50.0 g of N’- (2-cyano-4-iodo-phenyl)-N, N-dimethyl formamidine of the formula-(8) obtained according to the process given in the above step (ii) 51.0 g 3-chloro-4-(3′- fluorobenzyloxy)aniline were charged . The reaction mass was maintained at 115- 120 C for about 2 Hrs., the cooled to 25-35 C and quenched into ice cold water. The pH of the reaction mass was adjusted to basic by slow addition of aqueous ammonia solution and the reaction mass was filtered and dried at 70-75 C.Dry weight: 93.0 gPurity: 83.64% by HPLCThe purity of the product is enhanced by adopting the following procedure.

According to the analysis of related databases, 202197-26-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NATCO PHARMA LIMITED; JYOTHI PRASAD, Ramanadham; ADIBHATLA KALI SATYA, Bhujanga rao; VENKAIAH CHOWDARY, Nannapaneni; WO2011/39759; (2011); A1;,
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Reference of 33863-76-2, A common heterocyclic compound, 33863-76-2, name is 1-Bromo-3-chloro-5-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.

Preparation 32 1-Bromo-3-chloro-5-methoxybenzene Sodium methoxide (2.20 ml of a 4.5M solution in methanol, 10.0 mmol) was added dropwise to a stirred solution of 1-fluoro-3-chloro-5-bromobenzene (1.00 g, 4.77 mmol) in methanol (28 ml) at room temperature under nitrogen. The reaction was heated under reflux for 3 days and cooled to room temperature. The mixture was concentrated under reduced pressure and the resulting yellow oil was dissolved in dichloromethane (30 ml). The resulting solution was washed with water (2*20 ml) dried over magnesium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel eluding with cyclohexane to provide the title compound (302 mg) as a colourless oil. 1H-NMR (400 MHz, CDCl3): delta=3.77 (s, 3H), 6.82 (s, 1H), 6.94 (s, 1H), 7.09 (s, 1H). Microanalysis: Found: C, 37.94; H, 2.75. C7H6BrClO requires C, 37.96; H, 2.73%.

The synthetic route of 33863-76-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jones, Lyn Howard; Mowbray, Charles Eric; Price, David Anthony; Selby, Matthew Duncan; Stupple, Paul Anthony; US2003/100554; (2003); A1;,
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Reference of 19393-92-1, 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 19393-92-1 as follows.

EXAMPLE 263 (+-)-{[5-chloro-7-(2,6-dichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}amine The title compound was prepared (0.072 g, 8percent) following the general procedure of Example 166 as a white solid, hydrochloride salt from (5-chloro-2-methoxyphenyl)boronic acid (5.0 g, 26.88 mmol) and 2-bromo-1,3-dichlorobenzene (12.14 g, 53.76 mmol). mp 234-236° C.

According to the analysis of related databases, 19393-92-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wyeth; US2005/261347; (2005); A1;,
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Related Products of 210532-25-5, 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. 210532-25-5 name is 3,5-Difluorobenzene-1-sulfonyl chloride, 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.

1.132 g (5.32 mmol) of 3,5-difluorobenzene-1-sulfonyle chloride is added under argon to a solution of 545 mg (3.55 mmol) of 5-amino-2-chloronicotinotrile in 20 mL of an anhydrous 1:1 mixture of THF and pyridine. The reaction medium is heated to 70C for 3 hours and let 12 additional hours under stirring at room temperature. The solvent is dry evaporated and the crude reaction product is redissolved in ethyl acetate and washed with several aqueous fractions. The organic phase is dried on magnesium sulfate, filtered, concentrated and then purified by silica gel chromatography to yield 784 mg (67%) of N-(6-chloro-5-cyanopyridin-3-yl)-3,5-difluorobenzene-sulfonamide. 1H NMR: deltaH ppm (400 MHz, DMSO) : 11,39 (1H, sl, NH), 8. 34 (1H, m, CHarom), 8,10 (1H, m, CHarom), 7,67 (1H, m, CHarom), 7,59 (2H, m, CHarom).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,5-Difluorobenzene-1-sulfonyl chloride, and friends who are interested can also refer to it.

Reference:
Patent; PIERRE FABRE MEDICAMENT; Sokoloff, Pierre; Cachoux, Frederic; EP2689778; (2014); A1;,
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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. 50638-46-5, name is 4-Bromo-3-chloroanisole, This compound has unique chemical properties. The synthetic route is as follows., Safety of 4-Bromo-3-chloroanisole

A mixture of 1 -bromo-2-chloro-4-methoxybenzene (1.5 g, 6.8 mmol), oxazole (878 mg, 12.7 mmol), /-BuOK (1.52 g, 13.5 mmol) and tetrakis (1.56 g, 1.35 mmol) in dioxane (10 mL) was heated to 100C under N2 atmosphere for 4 hr. After cooling to r.t., the reaction mixture was concentrated under reduced pressure to give the crude product which was purified by flash chromatography (silica gel, 0 to 25% EA in PE) to afford 2-(2-chloro-4-methoxyphenyl)oxazole (40) (600 mg, 42 % yield) as a yellow solid. LC-MS (ESI): mlz (M+l) 210.0.

According to the analysis of related databases, 50638-46-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PHARMACYCLICS LLC; CHEN, Wei; WANG, Longcheng; YAN, Shunqi; LOURY, David, J.; JIA, Zhaozhong, J.; FRYE, Leah, Lynn; GREENWOOD, Jeremy, Robert; SHELLEY, Mee, Yoo; ATALLAH, Gordana, Babic; ZANALETTI, Riccardo; CATALANI, Maria, Pia; RAVEGLIA, Luca, Francesco; (402 pag.)WO2016/4272; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 14862-52-3, name is 3,5-Dibromochlorobenzene, 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 14862-52-3, Safety of 3,5-Dibromochlorobenzene

3-cyanophenyl boronic acid (25.0 g, 0.17 mol) and 1,3-dibromo-5-chlorobenzene (23.0 g, 0.08 mol) Dissolved in 290 mL of tetrahydrofuran, 1.5 M aqueous potassium carbonate solution (90 mL) was added,Tetrakis- (triphenylphosphine) palladium (3.94 g, 0.34 mmol) was added thereto, followed by heating with stirring for 13 hours.The temperature was lowered to room temperature, the water layer was separated off, dried over anhydrous magnesium sulfate and concentrated under reduced pressureRecrystallization was performed using chloroform and ethanolWas dried to prepare the intermediate n (44.7 g, yield 83%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,5-Dibromochlorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; LG Chem, Ltd.; Lee Jeong-ha; Moon Jeong-uk; Jeong Min-u; Lee Dong-hun; Chae Mi-yeong; (49 pag.)KR2018/32517; (2018); A;,
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Some common heterocyclic compound, 2770-11-8, name is 2-(4-Chlorophenoxy)aniline, molecular formula is C12H10ClNO, 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. Quality Control of 2-(4-Chlorophenoxy)aniline

A stirred solution of Boc-glycine (1.50 mmol), PyBOP (1.60 mmol) and DIPEA (3.50 mmol) in dichloromethane (10 mL) was cooled to 0 C with an ice bath. To this solution 2-(4-chlorophenoxy)aniline (1.50 mmol), dissolved in a minimum amount of dichloromethane, was added dropwise. The reaction mixture was allowed to warm to room temperature and was then stirred for 24 h. Thereafter, an aqueous work-up was performed similar to that of compounds 1-8. The resulting oil was further purified by column chromatography over silica gel(dichloromethane/methanol 200:1) to give a slightly orange solid (358 mg, 0.95 mmol, 63%); m.p.: 50-51 C; IR (KBr): [cm-1] nu = 3409 (m, N-H), 3342 (s, N-H), 1691 (br, s, C=O); 1H-NMR: (600 MHz, DMSO-d6): delta [ppm] = 1.34 (s, 9H, CH3), 3.71 (d, J = 6.1 Hz, 2H, CH2), 6.87-7.06 (m, 3H, arom. H), 7.05-7.30 (m, 3H, arom. H), 7.35-7.53 (m, 2H, arom. H), 8.12 (d, J = 7.7 Hz, 1H, NH), 9.33 (s, 1H, NH); 13C-NMR (151 MHz, DMSO-d6) delta [ppm] = 28.00 (3C, CH3), 43.92 (CH2), 118.82, 119.90 (2C), 122.35, 124.15, 124.63, 129.70 (2C) (CH), 78.17, 127.17, 129.64, 146.09, 155.47, 155.86, 168.51 (C); EI-MS: m/z (%): 376.1 [M]+ (11), 219.1 [M – 157]+ (100); HREI-MS: calcd. for C19H21ClN2O4 376.11844, found 376.11803; HPLC: 96.3% at 254 nm, 96.3% at 280 nm; tR = 4.84 min, tM(DMSO) = 1.06 min(ACN/H2O = 60:40), lambdamax [nm] = 230; HPLC-gradient: 95.8%, tR = 12.80 min, tM(DMSO) = 1.28 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2770-11-8, its application will become more common.

Reference:
Article; Weidner, Thomas; Nasereddin, Abed; Preu, Lutz; Gruenefeld, Johann; Dzikowski, Ron; Kunick, Conrad; Molecules; vol. 21; 2; (2016);,
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19752-55-7, name is 1-Bromo-3,5-dichlorobenzene, 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. SDS of cas: 19752-55-7

After mixing compound 3-3 (10 g, 0.02 mol), 1-bromo-3,5-dichlorobenzene (7.2 g, 0.03 mol), tetrakis(triphenylphosphine)palladium(O) (0.92 mg, 0.79 mmol), sodium carbonate (5.6 g, 0.05 mol), toluene 130 mL, ethanol 33 mL, and distilled water 33 mL in a flask, the mixture was stirred at 120°C for 12 hours. After completing the reaction, the mixture was extracted with ethylacetate, and the obtained organic layer was dried with anhydrous magnesium sulfate and filtered. The solvent was then removed under reduced pressure, and the remaining substance was subjected to column chromatography to separate compound 3-4 (4.4 g, 35percent).

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

Reference:
Patent; ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.; AHN, Hee-Choon; YANG, Soo-Jin; MOON, Doo-Hyeon; JUN, Ji-Song; LEE, Tae-Jin; LEE, Kyung-Joo; KWON, Hyuck-Joo; KIM, Bong-Ok; WO2014/98518; (2014); A1;,
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Application of 1127-85-1, 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. 1127-85-1, name is 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of 2,4-dichloropyrrolo[1,2-f][1,2,4]triazine (4a) (0.5 g, 2.7 mmol) in 2-Propanol (6 mL) was added (S)-pyrrolidin-2-ylmethanol (0.39 mL, 4.0 mmol), DIPEA (1.39 mL, 8.0 mmol) and heated at 90 C for 1 hr. The reaction was cooled to room temperature and solid obtained was collected by filtration to afford (S)-(l-(2-chloropyrrolo[2,l-f][l,2,4]triazin-4- yl)pyrrolidin-2-yl)methanol (96a) (0.49 g, 73 % yield) as a white solid; NMR (300 MHz, DMSO-i/e): delta 7.70 (dd, J= 2.6, 1.4 Hz, 1H), 6.97 (dd, J= 4.7, 1.6 Hz, 1H), 6.80 – 6.57 (m, 1H), 5.15 (t, J = 5.7 Hz, 1H, D2O exchangeable), 4.87 (t, J= 5.7 Hz, 1H), 4.44 (d, J= 17.8 Hz, 1H), 4.05 – 3.82 (m, 1H), 3.72 – 3.39 (m, 2H), 2.22 – 1.84 (m, 4H). MS (ES+): 253.3, 255.3 (M+2); MS (ES-): 287.2, 289.2 (M+Cl).

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, 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
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