Month: May 2021

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. 2770-01-6, name is 4-Chloro-1H-imidazo[4,5-c]pyridine, A new synthetic method of this compound is introduced below., Quality Control of 4-Chloro-1H-imidazo[4,5-c]pyridine

To improve the selectivity for the ^-substitution by blocking the N7-position with sterically demanded groups, 6-chloro-3-deazapurine (7) was converted to N-protected 3- deazaadenine derivatives (21a-b) (Scheme 2). Our initial attempts to convert the 6-chloride to the N6-amino group by methanolic ammonia or hydrazine/Raney-nickel gave 3-deazaadenine (13) in poor yields. However, the reaction of 7 with NaN3 or LiN3 provided 3-deaza- tetrazolopurine (12)la in about 80% and 82% yields with about 20% of starting material (7), which could not be removed from 12 (Table 1), respectively. The same reaction for 3-deaza- tetrazolopurine (12) was investigated by addition of an ionic liquid (DMF- [emim]BF4).13 LiN3 (20% in water) and DMF-[emim]BF4 ionic liquid (10:1 v/v) at 80 0C for 6 h provided 3- deaza-tetrazolopurine (12) in quantitative yield without 7. The ionic liquid was readily recovered by simple filtration, and recycled.14

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; UNIVERSITY OF GEORGIA RESEARCH FOUNDATION, INC.; WO2007/47793; (2007); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 179897-90-6, The chemical industry reduces the impact on the environment during synthesis 179897-90-6, name is 1,3-Dibromo-2-chloro-5-fluorobenzene, I believe this compound will play a more active role in future production and life.

A scalable tube was charged with 1,3-dibromo-2-chloro-5-fluoroben;jene(1.0, 12.52 g, 43.4 mmoi), benzophepsilon?one iniine(H.26 g, 45.6 mmoi), sodium tert-Bupsilontoxide(8.26 g, 65.1 mmoi), and loluene(100 ml). The resulting mixture was thoroughly sparged with Argon, then followed by addition of Pd2(dba)Lambda(Q398 g, 0.434 mmoi) and (S)«B.NAP(0.81 1 g, 1.3 mmoi) and Argon sparge was repealed. Reaction was sealed and heated overnight to 85C using an oil bath. Reaction mixture was cooled down to ambient temperature, quenched with water(20ml). Toluene layer was isolated, concentrated and residue was a mixture of mono-coupling product and his-coupUng byproduct with ratio -4:1 by fc:JPLC area at 220 nm. Residue was dissolved in TlIF (70 ml), treated with 3M MCI (20 ml) at room temperature for 1 hour and basified with sat. -Na2CO3 (40 ml). THF layer was separated, washed with brine, concentrated and residue was purified by flash chromatography on silica gel and 12 was obtained as a light yellow solid( 6.32 g, 30.4 mmot, yield 70%.LC/MS: (M+HJ=ncrt ionized, f« – 0.9 min);1H NMR(CDCl3, 300 MHz) 6 ppm 4.32 (s, 2 H), 6.44(dd, J, <;? 9.82 Hz, J2 *2.78 Hz, 1 H), 6.77<;dd, J1« 7.91 Hz, J2 -- 2.64 Hz, I H). 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, 1,3-Dibromo-2-chloro-5-fluorobenzene, other downstream synthetic routes, hurry up and to see. Reference:
Patent; NOVARTIS AG; HUANG, Zilin; SENDZIK, Martin; WO2010/100127; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 90390-33-3,Some common heterocyclic compound, 90390-33-3, name is 3-Chloro-5-fluorobenzylamine, molecular formula is C7H7ClFN, 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 solution of 3-hydroxy-2-oxo-1-phenylpiperidine-3-carboxylic acid (80 mg) and 3-chloro-5-fluorobenzylamine (65 mg) in dichloromethane (15 ml) is stirred with triethylamine (0.14 ml) and propanephosphoric anhydride (T3P; 0.33 g) firstly at 0 C., then at RT for 1 h under nitrogen. When the reaction is complete, the mixture is diluted with dichloromethane and washed with 10% sodium bicarbonate solution and saturated NaCl solution. Filtration, evaporation and chromatography gives the product as colourless solid with a yield of 12% (15 mg); 10307] LCMS: mass found (M+1,377.0)10308] Method: A-0. 1% ofTFA in H20, B-O. 1% of TFA in ACN: flow-2.0 ml/min.10309] Column: X Bridge C8 (50×4.6 mm.3.5p)+ve mode10310] Rt (mm): 4.03 area % 92.24 (max), 91.79 (220 nm)10311] HPLC:10312] Method: A: 0.1% of TFA in H20, B: 0.1% ofTFA in ACN, flow rate:2.0 ml/min10313] COLUMN: XBridge C8 (50×4.6) mm, 3.5 tm10314] Rt (mm): 4.01 area % 94.30 (max), 94.44 (220 nm);

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Chloro-5-fluorobenzylamine, its application will become more common.

Reference:
Patent; MERCK PATENT GmbH; Heinrich, Timo; Zenke, Frank; Krier, Mireille; Friese-Hamim, Manja; Seenisamy, Jeyaprakashnarayanan; US2015/31670; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 179897-90-6, name is 1,3-Dibromo-2-chloro-5-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 179897-90-6, Formula: C6H2Br2ClF

EXAMPLE 185 6-(3-Bromo-2-chloro-5-fluorophenyl)-1,2-dihydro-2,2A-trimethylquinoline (Compound 285, structure 4 of Scheme II, where R1 =3-bromo-2-chloro-5-fluorophenyl) This compound was prepared according to General Method 2 (EXAMPLE 9) from Compound 9 (143.3 mg, 0.45 mmol) and 1-chloro-2,6-dibromo-4-fluorobenzene (129.9 mg, 0.45 mmol). The crude material was purified by flash column chromatography (50 mL silica, hexane) followed by reverse phase preparatory TLC (1000 mL ODS, 80% methanol/water) to afford 4.3 mg (3%) of Compound 285. Data for Compound 285: 1 H NMR (400 MHz, acetone-d6) 7.50 (dd, J=7.8, 3.0, 1 H), 7.19 (dd, J=9.2, 3.0, 1 H), 7.10 (d, J=2.0, 1 H), 7.03 (dd, J=8.1, 2.0, 1 H), 6.55 (d, J=8.3, 1 H), 5.61 (s, 1 H), 5.37 (s, 1 H), 1.97 (s, 3 H), 1.29 (s, 6 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Dibromo-2-chloro-5-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5696130; (1997); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 21397-08-0, name is 2-Chloro-3-fluoroaniline, 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 21397-08-0, Recommanded Product: 21397-08-0

c) 2-Chloro-3-fluorophenylisothiocyanate Into a solution of 2-chloro-3-fluoroaniline (2.61 g, 17.94 mmol) in 50 mL of toluene at room temperature, thiophosgene (2.1 mL, 26.91 mmol) and triethylamine (3.02 mL, 26.91 mmol) was added. The mixture was stirred at room temperature for 16 hours. The mixture was partitioned between ethyl acetate and water. The combined organic layer was then concentrated to give the desired product (2.99 g, 89%). 1H NMR (CDCl3) delta 7.10 (m, 1H), 7.22 (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; Palovich, Michael R.; Widdowson, Katherine L.; Nie, Hong; US2003/216375; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 1000572-88-2, 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. 1000572-88-2 name is 2,5-Dibromo-1-chloro-3-fluorobenzene, 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.

An autoclave equipped with a stir bar was charged with 2,5-dibromo- l-chloro-3-fluorobenzene (5.0 g, 17.3 mmol), triethylamine (12.1 mL, 86.7 mmol), bis(diphenylphosphino)ferrocene)palladium(II) Chloride (0.86 mmol, 708 mg) and methanol (100 mL) was degassed with nitrogen for 10 min. Then the container was sealed and filled with CO to 400 psi. The reaction mixture was heated at 100 C with stirring for 12 hours. The reaction mixture was filtered through Celite, washed with MeOH, and the filtrate was concentrated. The crude product was purified by silica gel chromatography (0-10% EtOAc/hexane) to afford the title compound as a colorless oil which solidified in high vacuum (3.06 g, 71% yield). ¾ NMR (400 MHz, CDC13) delta 7.90 (s, 1H), 7.69 (dd, J = 9.0, 1.2 Hz, 1H), 3.99 (s, 3H), 3.95 (s, 3H). LCMS (APCI+) 247.0[M+H]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,5-Dibromo-1-chloro-3-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BLENCH, Toby; ELLWOOD, Charles; GOODACRE, Simon; LAI, Yingjie; LIANG, Jun; MACLEOD, Calum; MAGNUSON, Steven; TSUI, Vickie; WILLIAMS, Karen; ZHANG, Birong; WO2012/35039; (2012); 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. 2729-36-4, name is 4,5-Dichloro-2-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H4Cl2FN

In brief, 3,4-Dicliloro-6-fluoroaniline (1 equivalent, prepared as described in U.S. Patent No. 6,126,917) was reacted with 4-chloro-7-fluoro-6-nitroquinazoline (3.5 equivalents, Compound 24, prepared as described hereinabove), in a mixture of iso-propylalcohol/ dichloromethane. After filtration, 4,5-dichloro-2-fluoro-phenyl-(7-fluoro-6-nitro- quinazolin-4-yl)-amine was obtained.

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 2729-36-4.

Reference:
Patent; T.K. SIGNAL LTD.; WO2007/29251; (2007); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 327-76-4, name is 1-Chloro-2,4-bis(trifluoromethyl)benzene, 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 327-76-4, HPLC of Formula: C8H3ClF6

[0199] To a solution of 95 (25.0 g, 0.10 mol) in anhy. THF (150 mL) was added NaOCH3 (7.0 g, 0.13 mol) at 0C. The mixture was then heated at 50C for 6 h. After cooling to 25C, the reaction mixture was quenched with sat. NH4C1, diluted with EtOAc, washed with brine, and concentrated in vacuo to afford crude methyl ether 96 (17.93 g, 73%) as a colorless liquid. This product was sufficiently pure to be used directly in subsequent reaction. 1H NMR (400 MHz, CDC13) : 8 7.83 (1H, s), 7.77 (1H, d, J = 8. 4 Hz), 7.09 (1H, d, J= 8.4 Hz), 3.97 (3H, s) ppm. A solution of methyl ether 96 (9.98 g, 0.04 mol) in anhyrous CH2C12 (150 mL) was cooled to-78C and treated with BBr3 (6.0 mL, 0.063 mol). The resultant brown mixture was stirred for 1 h at-78C, and then warmed up to 25C over 4 h, and then quenched with water. The organic layer was separated and washed with sat. NaHCO3 and brine, dried over Na2S04, concentrated to-13 mL in vacuo below 0C and used directly in the following substitution reaction. Take this solution (ca. 1.15 mL) and diluted with DMF (8 mL), and then treated with K2CO3 (1.27 g) and bromide 79 (1.72 g). The resultant mixture was stirred at room temperature for 1 h, diluted with EtOAc, washed with water and brine, dried over Na2S04, and concentrated in vacuum. The residue was purified by flash chromatography (5: 95 EtOAc/hexanes) on silica gel and then recrystallized with 10 % EtOAc/hexanes to give pure ester 97 as a white solid. 1H NMR (400 MHz, DMSO-d6) : No. 8. 60 (1H, d, J= 2.2 Hz), 8.17 (1H, dd, J= 8.6, 2.2 Hz), 7.96 (1H, s), 7.91 (1H, d, J= 8.6 Hz), 7. 84 (1H, d, J= 8.2 Hz), 7.74 (1H, t, J= 7.8 Hz), 7.38 (1H, d, J= 9.0 Hz), 6.40 (1H, s), 4.19 (2H, m), 1.11 (3H, t, J = 7.2 Hz) ppm.

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; METABOLEX, INC.; WO2005/80340; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 697-88-1,Some common heterocyclic compound, 697-88-1, name is 4-Bromo-2,6-dichloroaniline, molecular formula is C6H4BrCl2N, 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.

Pd (OAc) 2 (186 mg), P (o-Tol) 3 (505 mg), Et3N (1.73 ml), 4-bromo-2,6- dichlorobenzeneamine (2.0 g) and acrylamide (885 mg) were dissolved in MECN (15 ml) and N2 was bubbled through the reaction mixture for at least 20 minutes. Then a cooler was mounted strictly under nitrogen atmosphere. The reaction mixture was heated at 70 C overnight. The reaction mixture was allowed to cool to 20 C and was diluted with CH2CI2 and washed with saturated aqueous NAHC03 (2x) and dried with brine and NA2SO4. The residue was sonicated in diisopropyl ether and filtered off. Yield: 0.55 g of intermediate 18 (30%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-2,6-dichloroaniline, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; ARTS, Theodora, Joanna, Francisca; JANSSEN, Graziella, Maria, Constantina; JANSSEN, Herwig, Josephus, Margareta; JANSSEN, Jasmine, Josee, Werner; JANSSEN, Paul, Peter, Maria; JANSSEN, Maroussia, Godelieve, Frank; WO2004/74266; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 167404-32-2, A common heterocyclic compound, 167404-32-2, name is 4-Cyclopropylbenzene-1-sulfonyl chloride, molecular formula is C9H9ClO2S, 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.

Compound 46. Crude compound 45 (13.3 g) was dissolved in 200 mL of acetone and 60 mL of water. Potassium fluoride (7.12 g, 122 mmol) was added and the reaction mixture was stirred overnight at rt. The reaction mixture was diluted with EtOAc and washed with water. The organic layer was dried with Na2SO4, filtered, and concentrated to dryness to give 9.80 g (97%) of crude p-cyclopropyl benzenesulfonyl fluoride (Compound 46).

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; Schering Corporation; US2003/232859; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics