Author: Jessica.F

1303588-27-3, name is 7-Chloro-1,2,3,4-tetrahydro-1,8-naphthyridine, 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. Computed Properties of C8H9ClN2

Under a nitrogen atomosphere, 1 , 2, 3,4-tetrahydro- 1 ,8-naphthyridine (110; 1 .2g, 7. 12mmol) was dissolved in DME (40mL) along with , 3-(tri fluromethyl)-phenylboronic acid (2.03g, 1 0.68 mmol), Cs2C03 (4.64 g, 14.24 mmol) and Pd(dppf)Cl2 (297 mg, 0.356 mmol). The reaction mixture was stirred at 90 C overnight. The solid was filtrated. The filtration was then diluted with H2O and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2S04 and then concentrated in vacuo. The residue was purified by column chromatography to afford 7-(3-(trifluoromethyl)phenyl)- 1 ,2, 3 , 4-tetrahydro- 1 ,8-naphthyridine (111 ; 1.25g, 63%). MS (ESI) calcd for C sH nFs^ (m/z) 278.27.

The synthetic route of 1303588-27-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; NG, Pui, Yee; BLUM, Charles; MCPHERSON, Lauren; PERNI, Robert, B.; VU, Chi, B.; AHMED, Mohammed, Mahmood; DISCH, Jeremy, S.; WO2011/59839; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 1017777-58-0, 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. 1017777-58-0, name is 2-Chloro-6-fluoro-3-methoxyaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2-chloro-6-fluoro-3-methoxy-aniline (0.85 g, 4.84 mmol, 1.0 eq) in DCM (8 mL) at 0C was added BBr3 (6.06 g, 24.2 mmol, 5.0 eq). The mixture was stirred at room temperature under N2 overnight, then poured into ice-water. The pH of the solution was adjusted to pH 6 by addition of sat.NaHC03. The dichloro methane was removed under reduced pressure and the aqueous residue was extracted with EtOAc. The combined organic extracts were washed with brine, dried (Na2SC>4), filtered and evaporated in vacuo to give the title compound as a pale yellow solid (0.74 g, 95 %).LC-MS: m/z 162.0, 164.0 [M+H]1H NMR (400 MHz, DMSO-d6) delta 9.67 (s, 1H), 6.80 (dd, JJ= 8.9, 4.6 Hz, 1H), 5.20 (br s, 2H)

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-Chloro-6-fluoro-3-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FOVEA PHARMACEUTICALS; FEUTRILL, John; LERICHE, Caroline; MIDDLEMISS, David; WO2013/37705; (2013); A2;,
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. 202865-57-4, name is 1-Bromo-2,5-dichloro-3-fluorobenzene, A new synthetic method of this compound is introduced below., Quality Control of 1-Bromo-2,5-dichloro-3-fluorobenzene

To a solution of 12a (0.450 g; 2.160 mmol) and NMP (5 mL) was added K2CO3 (0.896 g; 6.48 mmol) and 1-bromo-2,5-dichloro-3-fluoro-benzene (0.580 g; 2.38 mmol). The reaction was heated to 120 C. and monitored by TLC. After 8 h the reaction was cooled to RT and 10% HCl was added. The mixture was extracted with EtOAc and the combined extracts were washed with H2O and brine. The extracts were dried (Na2SO4), filtered and evaporated. The crude product was purified by SiO2 chromatography eluting with a gradient of hexane/EtOAc (100:0 to 60:40) to afford 146.

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; Roche Palo Alto LLC; US2005/239881; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 1303588-27-3, 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. 1303588-27-3, name is 7-Chloro-1,2,3,4-tetrahydro-1,8-naphthyridine, This compound has unique chemical properties. The synthetic route is as follows.

The mixture of 7-chloro-l,2,3,4-tetrahydro-l,8-naphthyridine (110; 6.0 g, 35.7 mmol), Boc20 (15.6 g, 71.4 mmol) and 4-Dimethylaminopyridine (DM AP) (13.1 g, 107.1 mmol) in THF(200 mL) was stirred under reflux for overnight. TLC showed the reaction was complete and the mixture was poured into water. The organic layer was dried over anhydrous Na2S04, filtered and concentrated to give /er/-butyl 7-chloro-3,4-dihydro-l,8-naphthyridine-l(2H)-carboxylate (112; 8.74 g, 91%) as a white solid. MS (ESI) calcd for C13H17CIN2O2 (m/z) 268.74.

The chemical industry reduces the impact on the environment during synthesis 7-Chloro-1,2,3,4-tetrahydro-1,8-naphthyridine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; NG, Pui, Yee; BLUM, Charles; MCPHERSON, Lauren; PERNI, Robert, B.; VU, Chi, B.; AHMED, Mohammed, Mahmood; DISCH, Jeremy, S.; WO2011/59839; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 208186-78-1,Some common heterocyclic compound, 208186-78-1, name is 1,2-Dibromo-5-chloro-3-fluorobenzene, molecular formula is C6H2Br2ClF, 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.

Intermediate 10; 3-(2-Bromo-4-chloro-6-fluoro-phenyl)-5-methyl-[1,2,4]oxadiazole Step A: 2-Bromo-4-chloro-6-fluoro-benzaldehyde To a solution of 1,2-dibromo-5-chloro-3-fluoro-benzene (10 g, 34.68 mmol) in heptane (27 ml) was added THF (44 ml) and the mixture was cooled to -45 C. Then iPrMgCl (38.14 ml, 38.14 mmol, 1M solution in THF) was added dropwise to the reaction mixture maintaining the temperature between -40 C. to -45 C. The mixture was stirred for 30 minutes at -40 C. before DMF (13.4 ml, 173.4 mmol) was added dropwise to the reaction mixture maintaining the temperature between -45 C. to -20 C. After stirring for another 15 minutes at -20 C., the reaction mixture was poured into a mixture of 2N HCl (20 ml) and ether (50 ml) at 0 C. The organic layer was separated and the aqueous layer was extracted two times with ether. The combined organic layers were dried with Na2SO4 and evaporated in vacuo to obtain the title compound as yellow solid (7.8 g, 95%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,2-Dibromo-5-chloro-3-fluorobenzene, its application will become more common.

Reference:
Patent; Aebi, Johannes; Binggeli, Alfred; Hertel, Cornelia; Konkar, Anish Ashok; Kuehne, Holger; Kuhn, Bernd; Maerki, Hans P.; Wang, Haiyan; US2012/165338; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 1481-63-6, A common heterocyclic compound, 1481-63-6, name is 1-Bromo-2,4-dichloro-5-fluorobenzene, molecular formula is C6H2BrCl2F, 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 5 65.4 ml of butyl acrylate, 450 mg of palladium acetate, 1.075 g of triphenylphosphane, 0.815 g of bis(phenylphosphino)ethane and 20.15 g of sodium acetate are added to 50.0 g of 1-bromo-2,4-dichloro-5-fluorobenzene under protecting gas and the mixture is dissolved in 100 ml of dimethylacetamide. The reaction mixture is boiled for 12 hours at 140-145 C. The mixture is then diluted with 200 ml of dichloromethane and washed twice by shaking with 100 ml of water. The organic phase is concentrated by a rotary evaporator. Yield: 86% of butyl 2,4-dichloro-5-fluorocinnamate.

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; Hoechst Aktiengesellschaft; US5516932; (1996); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 2162-98-3,Some common heterocyclic compound, 2162-98-3, name is 1,10-Dichlorodecane, molecular formula is C10H20Cl2, 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.

1,10-Dichlorodecane (8.73 g, 41.3 mmol) and triethylamine (6 mE) were added to a solution of m-aminophenol (3.85 g, 35.3 mmol) in DMF (40 mE). The mixture was stirred at 1000 C. for 3 days. The reaction was quenched with sam- 40 rated aqueous NaHCO3 and extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, hexane_EtOAc=9:i to 1:1) to give the title compound (1.92 g, 6.76 mmol, 19% yield). Brown oil; R1=0.57 (33% EtOAc-hexane); ?H NMR (600 MHz, DM50- d5) oe 8.84 (s, 1H), 6.80 (dd, J=7.6, 8.3 Hz, 1H), 5.97 (d, J=7.6 Hz, 1H), 5.94 (s, 1H), 5.92 (d, J=8.2 Hz, 1H), 5.36 (s, 1H), 50 3.61 (m, 2H), 2.89 (m, 2H), 1.69 (m, 2H), 1.49 (m, 2H),1.35-1.25 (m, 12H); ?3C NMR (150 MHz, DMSO-d5) oe158.3, 150.6, 129.5, 103.7, 103.0,98.9,45.6,43.1,32.2,29.2,29.1 x2, 28.9,28.4,26.9,26.4; FABMS m/z 283 [M]; HRMS calcd. for C,6H26N0C1 [M] 283.1703. found 283.1708. 55theoil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,10-Dichlorodecane, its application will become more common.

Reference:
Patent; KYOTO UNIVERSITY; Uesugi, Motonari; Hirata, Nao; Murata, Asako; Chang, Young-Tae; Nakatsuji, Norio; Suemori, Hirofumi; Kawase, Eihachiro; Yamauchi, Kaori; Ueda, Kazumitsu; Fujibayashi, Yuto; Yamanaka, Shinya; Nakagawa, Masato; (34 pag.)US9335323; (2016); B2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 106246-33-7, 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 106246-33-7 as follows.

EXAMPLE 1a Production of 4,4′-methylene-bis-(3-chloro-2,6-diethylphenylisocyanate) 100 g (0.26 mmol) of 4,4′-methylene-bis-(3-chloro-2,6-diethylaniline) was introduced into 1000 g of dichlorobenzene in an autoclave at room temperature. 57 g (0.58 mol) of phosgene was introduced into this solution over a period of 30 minutes. The reaction mixture was stirred in a sealed autoclave at 80 C. for 1 hour. Then, it was depressurized, and the hydrochloric acid that was produced, the excess phosgene, and the solvent were removed. In this case, the title product resulted in a yield of 110 g (98% of theory). Other data concerning the product is: IR (KBr): 2288.1 cm-1 1 H-NMR (CDCl3, 400 MHz) in ppm: 6.69 s, 2H; 4.12 s, 2H; 2.91 q, 4H, J=7.5 Hz; 2.59 q, 4H, J=7.6 Hz; 1.20 t, 6H, J=7.6 Hz; 1.15 t, 6H, J=7.5 Hz.

According to the analysis of related databases, 106246-33-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Lonza AG; US5734076; (1998); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 16429-44-0, name is 5-Bromo-3-chlorobenzene-1,2-diamine, 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 16429-44-0, SDS of cas: 16429-44-0

5-bromo-7-chloro-1H-benzimidazole A solution of 5-bromo-3-chlorobenzene-1,2-diamine (2 g, 9.03 mmol) in formic acid (30 ml) was heated at reflux for 16 hours. The reaction progress was monitored by LCMS. Reaction mixture was concentrated under vacuum to yield brown oil. The mixture was extracted by EtOAc from a saturated aqueous solution of NaHCO3, dried over MgSO4 and evaporated under vacuum to yield 5-bromo-7-chloro-1H-benzo[d]imidazole as a pale yellow solid. Mass spectrum (EI, m/z): Calculated for C7H4BrClN2, 232.5 (M+H), found 233.0.

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, 5-Bromo-3-chlorobenzene-1,2-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Janssen Pharmaceutica NV; Zhang, Xuqing; Macielag, Mark J.; (179 pag.)US2019/47959; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 204930-37-0, 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. 204930-37-0, name is 5-Bromo-1,3-dichloro-2-methylbenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Preparation 10; 5-bromo-2-(bromomethyl)-l,3-dichlorobenzene; Heat to reflux a solution of 5-bromo-l,3-dichloro-2-methylbenzene (97 mg, 0.40 mmol), N-bromosuccinimide (76 mg, 0.425 mmol) and benzoyl peroxide (16 mg, 0.06 mmol) in CCl4 (5 mL) for 3 hours under N2. Cool the reaction to room temperature and concentrate to an orange residue. Purify the residue by silica gel chromatography eluting with hexanes to afford 112 mg (87percent) of the product as white crystals.

The synthetic route of 5-Bromo-1,3-dichloro-2-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WALLACE, Owen, Brendan; WO2007/127726; (2007); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics