Tag: M.W=200-300

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. 89794-02-5, name is 4-Bromo-2-chlorotoluene, A new synthetic method of this compound is introduced below., Computed Properties of C7H6BrCl

A degassed mixture of 4-bromo-2-chloro-l-methylbenzene (0.600 g, 2.92 mmol, Aldrich 528889), 2-(cyclopent-l-en-l-yl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (0.680 g, 3.50 mmol, Combi-Blocks, PN-2510), Na2C03 (2.0 M solution, 4.4 mL, 8.8 mmol) and [1,1′- bis(diphenylphosphino)ferrocene]palladium(II) dichloride complex with dichloromethane (162 mg, 0.198 mmol) in MeCN (5 mL) was heated in a sealed vial to 110 C in an oil bath for 3 hours. The reaction was cooled to room temperature and partitioned between EtOAc and water. The organic layer was washed with water, followed by brine, dried over Na2S04, filtered and concentrated. The product was purified by flash chromatography, eluting with a gradient from 0-50% EtOAc in hexanes (520 mg, 92%). NMR (400 MHz, CDC13) delta 7.42 (d, J= 0.9 Hz, 1H), 7.25 (dd, J = 7.9, 1.3 Hz, 1H), 7.17 (d, J = 7.9 Hz, 1H), 6.20 – 6.16 (m, 1H), 2.73 – 2.65 (m, 2H), 2.59 – 2.50 (m, 2H), 2.38 (s, 3H), 2.10 – 1.96 (m, 2H).

The synthetic route of 89794-02-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INCYTE CORPORATION; DOUTY, Brent; BUESKING, Andrew W.; BURNS, David M.; COMBS, Andrew P.; FALAHATPISHEH, Nikoo; JALLURI, Ravi Kumar; LEVY, Daniel; POLAM, Padmaja; SHAO, Lixin; SHEPARD, Stacey; SHVARTSBART, Artem; SPARKS, Richard B.; YUE, Eddy W.; (355 pag.)WO2019/79469; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 61881-19-4, 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. 61881-19-4 name is 2,2,2-Trifluoro-N-phenylacetimidoyl 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.

3.1.16 Methyl 4-O-acetyl-2,3-di-O-benzyl-alpha-d-galactopyranosyluronate-(1?2)-3,4-di-O-benzyl-alpha-l-rhamnopyranosyl 1-N-phenyltrifluoroacetimidate (26) To a solution of 25 (261 mg, 0.33 mmol) in dry THF/MeOH (5.0 mL/5.0 mL), PdCl2 (28 mg, 0.16 mmol) was added. After being stirred at room temperature for 5 h, the solution was filtered through Celite and concentrated under vacuum. The resulting syrup was purified by chromatography on silica gel (petroleum ether/ethyl acetate, 2.5:1) to provide the hemiacetal as a colorless syrup (236 mg, 95%). To a solution of the hemiacetal (216 mg, 0.28 mmol) in acetone (2.5 mL), K2CO3 (116 mg, 0.84 mmol), and N-phenyl trifluoroacetimidoyl chloride (118 mg, 0.56 mmol) were added. After stirring at ambient temperature for 4 h, the mixture was filtered and concentrated in vacuo. The resulting residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 6:1) to afford 26 (242 mg, 92%), which was used directly without characterization.

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

Reference:
Article; Ma, Yuyong; Cao, Xin; Yu, Biao; Carbohydrate Research; vol. 377; (2013); p. 63 – 74;,
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. 110407-59-5, name is 2-Chloro-4-fluorobromobenzene, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C6H3BrClF

Step 1 : tert-butyl 4-(2-chloro-4-fluorophenyl)piperazine-l-carboxylate (0979) [00342] To the solution of A18-1 (200 mg, 1 mmol, 1.0 eq), Pd2(dba)3 (44 mg, 48 umol, (0980) 0.05 eq), BINAP (60 mg, 0. 1 mmol, 0. 1 eq), f-BuONa (184 mg, 1.9 mmol, 2.0 eq) in toluene (5 mL) was added fert-butyl piperazine- l-carboxylate (267 mg, 1.4 mmol, 1.5 eq). The mixture was stirred at 1 10 C for 16 hr. The reaction was monitored by TLC. The reaction was concentrated under reduced pressure. The residue was purified by column chromatography (Si02, Petroleum ether/Ethyl acetate=20: 1) to give the A18-2 (187 mg, 0.6 mmol, 62.2% yield) as a yellow oil.

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 110407-59-5.

Reference:
Patent; VIVACE THERAPEUTICS, INC.; LIN, Tracy Tzu-Ling Tang; KONRADI, Andrei W.; VACCA, Joseph; SHEN, Wang; COBURN, Craig; (231 pag.)WO2017/58716; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 110407-59-5, These common heterocyclic compound, 110407-59-5, name is 2-Chloro-4-fluorobromobenzene, 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.

Step E: Preparation of 4-chloro-a-(2-chloro-4-fluorophenyl)-l-(2,6-difluorophenyl)- lH-imidazole-5 -methanol; To a mixture of l-bromo-2-chloro-4-fluorobenzene (0.12 mL, 0.99 mmol) in tetrahydrofuran (5 mL) at about -78 C was added dropwise over 5 minutes n-butyllithium (2.5 M in hexanes, 0.37 mL, 0.94 mmol) while maintaining the temperature of the reaction mixture below -65 C. After the addition was complete, 4-chloro-l-(2,6-difluorophenyl)- lH-imidazole-5-carboxaldehyde (i.e. the product of Step D) in tetrahydrofuran (2 mL) was added dropwise to the reaction mixture while maintaining the reaction mixture at about -62 to -65 C. After 20 minutes, saturated aqueous ammonium chloride solution (5 mL) was added in one portion to the reaction mixture, the mixture was allowed to warm to ambient temperature (about 20 C), and then water (1 mL) was added. The resulting mixture was poured onto a solid phase extraction tube (Varian Chem Elute, prepacked with diatomaceous) and eluted with ethyl acetate (50 mL). The ethyl acetate eluant was concentrated under reduced pressure and the resulting material was triturated with ethyl acetate -hexanes to provide a solid. The solid was recrystallized from ethyl acetate-hexanes to provide the title compound, a compound of the present invention, as a solid (0.080 g). in NMR (DMSO- ): delta 7.71 (m, 1H), 7.45-7.35 (m, 4 H), 7.20 (m, 1H), 6.68 (m, 1H), 6.24 (br s, 1H), 5.71 (s, 1H).

Statistics shows that 2-Chloro-4-fluorobromobenzene is playing an increasingly important role. we look forward to future research findings about 110407-59-5.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; LONG, Jeffrey, Keith; BEREZNAK, James, Francis; KAR, Moumita; TAGGI, Andrew, Edmund; CHEN, Yuzhong; WO2012/44650; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 41965-95-1, name is 3-Chloro-4-methoxybenzylamine Hydrochloride, molecular formula is C8H11Cl2NO, 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. category: chlorides-buliding-blocks

10-[(3-chloro-4-methoxybenzyl)amino]-2-methyl-1,2,3,4-tetrahydrobenzo[b][1,6]naphthyridine-8-carbonitrile A mixture of 4 (0.12 mmol), 3-chloro-4-methoxybenzylamine hydrochloride (0.12 mmol), NaI (0.006 mmol), and phenol (0.12 mmol) was heated at 130 C. for 2.5 h. The reaction mixture was diluted with Et2O (10 mL) and washed with 1N NaOH (3*5 mL). The organic layer was dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by Flash Chromatography (AcOEt:MeOH 8:2) to give the desired compound B (33% of yield). MS ESI (m/z) 394 (M+H)+, 1H NMR (300 MHz, CDCl3) delta 8.32 (d, 1H, J=1.2 Hz), 7.97 (d, 1H, J=8.7 Hz), 7.71 (dd, 1H, J1=1.8, J2=8.7 Hz), 7.37 (d, 1H, J=2.1 Hz), 7.18 (dd, 1H, J1=2.4, J2=8.7 Hz), 6.94 (d, 1H, J=8.4 Hz), 4.57 (d, 2H, J=6.0 Hz), 4.11 (br s, 1H), 3.92 (s, 3H), 3.54 (s, 2H), 3.22 (t, 2H, J=6.3 Hz), 2.83 (t, 2H, J=6.3 Hz), 2.52 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 41965-95-1, its application will become more common.

Reference:
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; Landry, Donald W.; Deng, Shixian; Arancio, Ottavio; Fiorito, Jole; Wasmuth, Andrew; (41 pag.)US10626113; (2020); B2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 50638-47-6, name is 4-Bromo-2-chloro-1-methoxybenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C7H6BrClO

To a 5 ml of toluene solution containing 0.20 g of 3 (S) -aminopyrrolidine-1-carboxylic acid tert-butyl ester (1.1 mmol) and 0.238 g of 2-chloro-3-bromoanisole (1.1 mmol) were added 67.0 mg of BINAP (0.11 mmol), 24 mg of tris (dibenzylideneacetone) dipalladium (0.027 mmol) and 144 mg of sodium tert-butoxide (1.5 mmol). The mixture was heated under reflux under a nitrogen atmosphere at 100,C for one hour. After cooling to room temperature, the reaction solution was filtered EPO using Celite. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane : ethyl acetate = 10 : 1 ? 3 : 1) . The purified product was concentrated to dryness under reduced pressure to thereby obtain 0.28 g of light yellow amorphous solid 3 (S) – (3-chloro-4-methoxyphenylamino)pyrrolidine-l-carboxylic acid tert-butyl ester. 1H-NMR(CDCl3) deltappm: 1.47(9H,s), 1.80-1.90 (IH,m) , 2.10-2.20 (lH,m) , 3.10-3.25 (IH,m) , 3.38-3.75(3H,m), 3.83(3H,s), 3.92-3.96 (IH,m) , 6.47 (IH,dd, J=2.8Hz, J=8.8Hz), 6.67 (IH, d, J=2.8Hz) , 6.81 (IH, d, J=8.8Hz) .

The synthetic route of 50638-47-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; WO2006/121218; (2006); A1;,
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. 38762-41-3, name is 4-Bromo-2-chloroaniline, A new synthetic method of this compound is introduced below., name: 4-Bromo-2-chloroaniline

a Tert-butyl N-(4-bromo-2-chlorophenyl)carbamate A solution of 4-bromo-2-chloroaniline (5.00 g, 0.0242 mol) in tetrahydrofuran (50 mL) was reacted with a 1.0 M solution of sodium bis(trimethylsilyl)amide in tetrahydrofuran (53.2 mL, 0.0532 mol). The mixture was stirred 15 minutes at ambient temperature. Di-tert-butyl dicarbonate (6.34 g, 0.0290 mol) was added and the solution was stirred for 2 hours. The solvent was removed in vacuo, and the crude material was purified by flash column chromatography on silica using heptane /ethyl acetate (4:1). The solvent was removed in vacuo to give tert-butyl N-(4-bromo-2-chlorophenyl)carbamate as a white solid (4.214 g, 0.0137 mol). 1H NMR (DMSO-d6, 400 MHz) delta 8.75 (s, 1H), 7.71 (d, 1H), 7.54 (d, 1H), 7.50 (dd, 5H), 1.46 (s, 9H); TLC (heptane/ethylacetate 4:1) Rf 0.54.

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; Abbott Laboratories; US2002/156081; (2002); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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 62356-27-8 as follows. name: 1-Bromo-3-chloro-2-methylbenzene

EXAMPLE 175 6-(3-chloro-2-methylphenyl)-1,2-dihydro-2,2,4-trimethylquinoline (Compound 275, Structure 4 of Scheme II, where R1 =3-chloro-2-methylphenyl) This compound was prepared according to General Method 2 (EXAMPLE 9) from Compound 9 (70.0 mg, 0.22 mmol) and 2-bromo-6-chlorotoluene (45.2 mg, 0.22 mmol). The crude material was purified by flash column chromatography (75 ml silica, hexane to 5% ethyl acetate/hexane) to afford 63.1 mg (96%) of Compound 275. Data for Compound 275: 1 H NMR (400 MHz, acetone-d6) 7.30 (d, J=8.3, 1 H), 7.16 (m, 1 H), 6.95 (s, 1 H), 6.87 (d, J=10.2, 1 H), 6.54 (d, J=8.0, 1 H), 5.36 (s, 1 H), 5.25 (s, 1 H), 2.03 (s, 3 H), 1.28 (s, 6 H).

According to the analysis of related databases, 62356-27-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5693646; (1997); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 1127-85-1, A common heterocyclic compound, 1127-85-1, name is 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline, molecular formula is C8H8Cl2N2, 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.

Step C: Synthesis of (2-chloro-5,6,7,8-tetrahydro-quinazolin-4-yl)-methyl-amine. To a solution of 2,4-dichloro-5,6,7,8-tetrahydro-quinazolin (8.70 g, 42.8 mmol) in THF (87 mL) was added 40% aqueous MeNH2 (8.32 g, 107 mmol). The mixture was stirred at ambient temperature for 8 hr. The solution was poured into saturated aqueous NaHCO3 and the aqueous layer was extracted with CHCl3 (three times). The combined organic layer was dried over MgSO4, filtrated, concentrated, and purified by flash chromatography (NH-silica, 50% EtOAc in hexane) to give (2-chloro-5,6,7,8-tetrahydro-quinazolin-4-yl)-methyl-amine (7.04 g, 83%) as a white solid. ESI MS m/e 220, M + Na+; 1H NMR (300 MHz, CDCl3) delta 1.74-1.92 (m, 4 H), 2.26 (t, J= 5.5 Hz, 2 H), 2.67 (t, J= 5.6 Hz, 2 H), 3.05 (d, J= 5.0 Hz, 3 H), 4.81 (s, 1 H).

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; Taisho Pharmaceutical Co. Ltd.; Arena Pharmaceuticals, Inc.; EP1464335; (2004); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 101-79-1,Some common heterocyclic compound, 101-79-1, name is 4-(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.

B. r4- (4-Chloro-phenoxy)-phenylaminol-acetic acid ethyl ester. Oxo-acetic acid ethyl ester (0.243 g, 2.38 mmol) was added to a solution of 4- (4-chloro- phenoxy)-phenylamine (0.5 g, 2.27 mmol) in DCE (48 mL). The mixture was stirred at rt for 15-20 min, before the addition of Na (OAc) 3BH (0.625 g, 2.95 mmol) and AcOH (0.24 mL). The mixture was stirred at rt for 5 h. More oxo- acetic acid ethyl ester (0.08 g) and AcOH (0.03 mL) were added, and the mixture was stirred at rt overnight. Saturated NaHCO3 (50 mL) and excess CH2CI2 (50 mL) were then added to the reaction mixture. The aqueous layer was extracted with CH2CI2 (3 X 50 mL). The combined organic layers were washed with brine (40 mL) and dried (MgS04), and the solvent was removed. Purification by column chromatography with 20-50percent EtOAc/hexanes afforded 0.4 g (61 percent) of the desired product. MS (electrospray) : mass calculated for Ct4H12CINO3, 305.76 ; m/z found, 306.1 [M+H] +.’H NMR (400 MHz, CDCI3) : 7.25-7. 23 (m, 2H), 6.93-6. 86 (m, 4H), 6.64-6. 62 (m, 2H), 4.28 (dd, J= 14.3, 7.1 Hz, 2H), 3.92 (s, 2H), 1.33 (t, J= 7.1 Hz, 3H).

The synthetic route of 101-79-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2005/44810; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics