Author: Jessica.F

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. 98446-49-2, name is 2,4-Dichloro-5-methoxyaniline, A new synthetic method of this compound is introduced below., Computed Properties of C7H7Cl2NO

EXAMPLE 4 Preparation of 4-[(2,4-dichloro-5-methoxyphenyl)amino]-5-(3,4-dimethoxyphenyl)nicotinonitrile 137 A mixture of 4-chloro-5-(3,4-dimethoxyphenyl)nicotinonitrile (0.5 g, 1.82 mmol), 2,4-dichloro-5-methoxyaniline (0.402 g, 2.1 mmol), Pd2(dba)3 (0.167 g, 0.18 mmol), 2-dicyclohexylphosino-2′-(N,N-dimethylamino)biphenyl (0.22 g, 0.56 mmol), and K3PO4 (0.58 g, 2.73 mmol) in 10 ml of DME was heated at reflux for 45 minutes. The hot mixture was filtered and solids were washed with ether. The combined filtrates were washed with saturated NaHCO3, dried (MgSO4), and filtered through a pad of Magnesol. Solvent was removed and the residue was chromatographed on silica gel. Product was eluted with CH2Cl2-ether and then recrystallized from iso-propanol/hexane giving 0.21 g of 4-[(2,4-dichloro-5-methoxyphenyl)amino]-5-(3,4-dimethoxyphenyl)nicotinonitrile 137. HPLC retention time(a): 0.86 min.; MS: 430.2 m/e (M+H). Following procedures analogous to those described for the preparation of compound 137 and using the appropriate aniline, the compounds in Table 3 were prepared.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Cole, Derek Cecil; Asselin, Magda; Boschelli, Diane Harris; Wissner, Allan; Wang, Yanong Daniel; Prashad, Amarnauth Shastrie; Dushin, Russell; US2007/287738; (2007); A1;,
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Some common heterocyclic compound, 60811-18-9, name is 4-Bromo-1-chloro-2-fluorobenzene, molecular formula is C6H3BrClF, 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. Computed Properties of C6H3BrClF

EXAMPLE 1 A mixture of 0.1 mole of 4′-n-propyl-4-biphenylboronic acid (obtained by the reaction of the Grignard reagent of 4′-n-propyl-4-bromobiphenyl and trimethyl borate), 0.1 mole of 4-chloro-3-fluorobromobenzene, tetrakis (triphenylphosphine) palladium (1 mole %), 2 m sodium carbonate solution (150 ml), toluene (250 ml) and IMS (60 ml) is stirred and refluxed for 16 hrs under a nitrogen atomosphere. After usual work-up 4-chloro-3-fluoro-4′-(p-n-propylphenyl) -biphenyl is obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 60811-18-9, its application will become more common.

Reference:
Patent; Merck Patent Gesellschaft mit beschrankter Haftung; US5482653; (1996); A;,
Chloride – Wikipedia,
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Related Products of 97329-43-6, 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 97329-43-6 as follows.

To a stirred solution of 3-bromo-6-chloropyrazin-2-amine (0.3 g, 1.43 mmol) in THF:H2O (20 ml, 9:1), and mixture of boronic acid and ester (0.3 g, crude), sodium carbonate (0.46 g, 4.31 mmol) were added. The reaction mixture was degassed with argon for a 10 minutes and Pd(PPh3)4 (0.16 g, 0.14 mmol) was added. The reaction mixture was degassed again with argon and heated at 80 C. with stirring for 12 h. Progress of the reaction was monitored by TLC, which showed complete consumption of starting material. The reaction mixture was allowed to cool to room temperature and concentrated. The residue was diluted with water (20 mL) and the extracted with EtOAc (3*20 mL). The combined organic layer was washed with brine (40 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography [silica gel (100-200 mesh), gradient 4% to 6% ethyl acetate in hexane] to give 6-chloro-3-(2-chloro-3-methylphenyl)pyrazin-2-amine (0.28 g, 76%) as a yellow solid. MS (ESI+ve): 253.92 1H-NMR (400 MHz; DMSO-d6): delta 7.82 (s, 1H), 7.44-7.46 (d, J=7.20 Hz, 1H), 7.32-7.36 (t, J=7.6 Hz, 1H), 7.20-7.22 (d, J=6.8 Hz, 1H), 6.51 (bs, 2H), 2.40 (s, 3H).

According to the analysis of related databases, 97329-43-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Krouzon Pharmaceuticals, Inc.; Volkmann, Robert; Marfat, Anthony; Nelson, Frederick; Zagouras, Panayiotis; (44 pag.)US2019/77792; (2019); A1;,
Chloride – Wikipedia,
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Application of 2106-04-9, A common heterocyclic compound, 2106-04-9, name is 3-Chloro-2-fluoroaniline, molecular formula is C6H5ClFN, 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.

a 2-Fluoro-3-chlorophenylisothiocyanate Into a solution of 2-fluoro-3-chloroaniline (1.0 g, 6.87 mmol) in 30 mL of toluene at room temperature, thiophosgene (0.8 mL, 10.3 mmol) and triethylamine (1.12 mL, 8.24 mmol) were added. The mixture was stirred at room temperature for 16 hours. The mixture was parationed between ethyl acetate and water. The combined organic layer was then concentrated to give the desired product (950 mg, 74%). 1H NMR (CDCl,) delta 7.09 (m, 2H), 7.30 (m, 1H).

The synthetic route of 2106-04-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Palovich, Michael R.; Widdowson, Katherine L.; Nie, Hong; US2003/216375; (2003); A1;,
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Application of 210532-25-5, These common heterocyclic compound, 210532-25-5, name is 3,5-Difluorobenzene-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.

N-(6-chloro-5-cyanopyridin-3-yl)-3,5-difluorobenzene-sulfonamide 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 70 C. 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, s1, NH), 8. 34 (1H, m, CHarom), 8.10 (1H, m, CHarom), 7.67 (1H, m, CHarom), 7.59 (2H, m, CHarom).

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

Reference:
Patent; PIERRE FABRE MEDICAMENT; KALOUN, El Bachir; BEDJEGUELAL, Karim; RABOT, Remi; KRUCZYNSKI, Anna; SCHMITT, Philippe; PEREZ, Michel; RAHIER, Nicolas; US2013/85144; (2013); A1;,
Chloride – Wikipedia,
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Related Products of 699-89-8, 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. 699-89-8, name is 4,7-Dichlorothieno[2,3-d]pyridazine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Equal equivalents of dichloride (1) and M-NH2 are refluxed in the appropriate amount of absolute ethanol at 95 C. for 2 hrs. The reaction mixture is allowed to cool to room temperature and the precipitate (2) that forms is filtered and washed sequentially with isopropyl alcohol, 4.0 N KOH, H2O, and hexane, and then dried. The filtrate (2) is then reacted with 1.2 equivalent of Q-NH2 in an appropriate amount of n-butyl alcohol at 150 C. for 10 hrs. The reaction is cooled to room temperature before the solvent is evaporated under reduced pressure. The residue is treated with aqueous 4.0 N KOH solution and extracted with dichloromethane. The organic layer is dried (MgSO4) and evaporated. The crude product (3) is purified by preparative thin layer chromatography (TLC) or flash chromatography on silica gel using dichloromethane/methanol (95:5) as the eluent. Final product is confirmed by LC/MS and/or NMR. The invention compounds of Examples 23-25, 48, and 76-80 as shown in the below table were prepared by method A-1.

The synthetic route of 4,7-Dichlorothieno[2,3-d]pyridazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Pharmaceuticals Corporation; US6689883; (2004); B1;,
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. 137384-48-6, name is 6-Chloro-3-methylimidazo[1,2-b]pyridazine, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 6-Chloro-3-methylimidazo[1,2-b]pyridazine

To 0.835 mmol of (S)-2-(4-methyl-1-(2-oxo-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl)-pyridin-1(2H)-yl)pentan-2-yl)isoindoline-1,3-dione in a microwaveable vial was added100 mg (0.597 mmol) of 6-chloro-3-methylimidazo[1,2-b]pyridazine, 98 mg (0.119 mmol) ofPdCI2(dppf)2.DCM, 2 mL of DME, and 2 mL of 2M KOAc aqueous solution. It was microwaved at 135C for 0.5 hr. It was diluted with EtOAc, washed with brine, filtered through a pad of celite in order to distinguish between the organic and aqueous layers. The organic layer was dried over MgSO4, concentrated and loaded onto a 40 gram silica gel column and purified on the ISCO eluting with 0-10% MeOH/DCM to obtain the desired. This product was subjected to the phthalimides deprotection procedure described in Example 5.6.28 to obtain the titled5 compound. 1H NMR (400 MHz, METHANOL-d4) ppm 1.02 (d, J=6.57 Hz, 3 H) 1.06 (d,J=6.57 Hz, 3 H) 1.54 – 1.67 (m, 2 H) 1.80 – 1.91 (m, 1 H) 2.66 (5, 3 H) 3.79 (qd, J=7.24,3.79 Hz, 1 H) 4.26 (dd, J=14.27, 7.71 Hz, 1 H) 4.36 (dd, J=14.40, 3.79 Hz, 1 H) 7.23 (dd,J=7.20, 1.89 Hz, 1 H) 7.29 (d, J=1.77 Hz, 1 H) 7.68 (5, 1 H) 7.75 – 7.83 (m, 2 H) 8.11 (d,J=9.60 Hz, 1 H). LRMS (ESI) m/z 326 [(M+H)], calc?d for C18H23N05: 325.

According to the analysis of related databases, 137384-48-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LEXICON PHARMACEUTICALS, INC.; BI, Yingzhi; GARDYAN, Michael Walter; GREEN, Michael Alan; GODWIN, Kumi; ZHANG, Yulian; WO2015/35167; (2015); A1;,
Chloride – Wikipedia,
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Electric Literature of 57946-56-2, 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. 57946-56-2, name is 4-Chloro-2-fluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 11 Production of the nitroaniline (XIII): 4-Chloro-2-fluoroaniline (23 g) was dissolved in conc. sulfuric acid (120 ml), and the resultant mixture was cooled to -20 C., followed by dropwise addition of fuming nitric acid (15 g). The reaction mixture was stirred at -20 to -15 C. for 1.5 hours, poured into ice-water and then extracted with ether. The ether extract was washed with water and a saturated sodium bicarbonate solution, dried and concentrated. The residue was crystallized from a mixture of toluene and hexane (2:1) to obtain 20 g of 4-chloro-2-fluoro-5-nitroaniline. m.p., 83-84.5 C.

The synthetic route of 4-Chloro-2-fluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Chemical Company, Limited; US4670043; (1987); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 118-69-4, name is 2,6-Dichlorotoluene, A new synthetic method of this compound is introduced below., category: chlorides-buliding-blocks

(1) In a 1000 ml four-necked flask,300 g of dimethylsulfoxide was added in this order,2,6-dichlorotoluene 100 g (0.62 mol)Heating up,When the temperature reaches 160 C,Dropping 200 gMethanol sodium methoxide solution (sodium methoxide content 28%, 1.04 mol)Methanol was added dropwise,Insulated at 160 C for 8 h.(2)Cooling to 80 ,0.1 g of catalyst PEG-600 (polyethylene glycol 600) was added,At this temperature, 20 g of methyl chloride (0.40 mol) was passed until the mass fraction of 6-chloro-2-hydroxytoluene was less than 1%, and the reaction was carried out for 2 hours.(3) cool to room temperature,And then negative pressure recovery DMSO,After treatment, 96.8 g of 6-chloro-2-methoxytoluene was obtained, the content was 96.0% and the yield was 95.6%.

The synthetic route of 118-69-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Yangnong Chemical Industry Co., Ltd; Jiangsu Youjia Plant Protection Co., Ltd; Zhou, Qikui; Jiang, Youfa; Zhu, Jianrong; Sun, Bing; Wang, Mingkun; Kuan, Jianbo; Xue, Yadong; (5 pag.)CN106518630; (2017); A;,
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202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)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. SDS of cas: 202197-26-0

Step A: preparation of 4-[3-chloro-4-(3-fluoro-benzyloxy)phenylamino]-6-nitroquinazoline 1.20 g (5.7 mmol) of 4-chloro-6-nitro-quinazoline (prepared by referring to) and 1.37 g (5.6 mmol) of 4-(3-fluoro-benzyloxy)-3-chloro-aniline (prepared by referring to) were dissolved in 80mL of isopropanol and refluxed for 3 hours. A large amount of yellow solid was precipitated from the system, and was filtered. The filter cake was washed with a saturated sodium bicarbonate solution till pH=8 and dried under vacuum to obtain 1.62g (3.75 mmol) of yellow solid, which was identified as the compound 4-[3-chloro-4-(3-fluoro-benzyloxy)phenylamino]-6-nitro-quinazoline with a yield of 67%. 1H-NMR(400MHz, CDCl3): delta11.30(1H, br), 9.54-9.48(1H, m), 8.45-8.41(1H, m), 8.31-8.25(1H, m), 7.98-7.89(1H, m), 7.50-7.47(1H, m), 7.35-7.26 (1H, m), 7.05-6.96(1H, m), 6.90-6.80(2H, m), 7.74-7.60(2H, m), 4.84(2H, s).

The synthetic route of 202197-26-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Allist Pharmaceutical., Inc.; EP2269994; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics