Category: 2106-04-9

Reference of 2106-04-9,Some common heterocyclic compound, 2106-04-9, name is 3-Chloro-2-fluoroaniline, molecular formula is C6H5ClFN, 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.

General procedure: A mixture of substituted aniline (0.8 mmol), potassiumcarbonate (553 mg, 4 mmol), and potassium iodide(13 mg, 0.08 mmol) in acetone (12 ml) was sitrred at roomtemperature. To the suspension, a solution of compound9 (179 mg, 0.8 mmol) was added in acetone (6 ml) dropwise.The reaction was stirred for 8 h and monitored byTLC. Solvent was removed under vaccum, followed bythe addition of ethyl acetate (40 ml) and water (30 ml).The organic layer was washed with water (30 ml × 1) andbrine (30 ml × 1), dried with anhydrous sodium sulfate,filtered, and concentrated. The crude material wasabsorbed onto silica gel and purified using 90% of petroleumether in ethyl acetate to yield title compound 10.

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

Reference:
Article; Guo, Guangzhu; Liu, Jianzhen; Wang, Guanjie; Zhang, Daoguang; Lu, Jinjie; Zhao, Guisen; Anti-Cancer Drugs; vol. 27; 4; (2016); p. 278 – 285;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

2106-04-9, name is 3-Chloro-2-fluoroaniline, 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. Product Details of 2106-04-9

To a mixture of 3-chloro-2-fluoroaniline (18.0 g, 124 mmol) in MeCN (100 mL) was added a solution of NBS (26.4 g, 148 mmol) in MeCN (100 mL) in a dropwise manner at 25 C. The mixture was stirred at 25 C for 4 h. The reaction mixture was concentrated in vacuo to give the crude product. The crude material was purified by silica-gel column chromatography (petroleum ether/EtOAc, 50:1) to give 4-bromo-3-chloro-2-fluoroaniline as a brown oil (18.0 g, yield: 65%). 1H NMR: (400 MHz, CD3OD) d: 7.13 (dd, J2 = 8.8 Hz, J2 = 2.0 Hz, 1H), 6.66 (t, / = 8.4 Hz, 1H).

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

Reference:
Patent; BIOGEN MA INC.; HOPKINS, Brian, T.; MA, Bin; PRINCE, Robin; MARX, Isaac; SCHULZ, Juergen; NEVALAINEN, Marta; DECHANTSREITER, Michael; (273 pag.)WO2019/222101; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

2106-04-9, name is 3-Chloro-2-fluoroaniline, 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 C6H5ClFN

Using a modified procedure described by Gomez-Sanchez. (Reference: GomezSanchez, A. et al., Anales Dc Quimica, 8 1(2): 139 (1985).) A clear, faint yellow solution of ethyl nitroacetate (4.17 ml, 37.6 mmol) and triethylorthoacetate (6.93 mL, 37.6 mmol)in toluene (9.39 mL) was heated to 110 C. A Dean-Stark trap was used to azeotrope the ethanol. Approximately every 30 mm, the solvent was removed from the Dean-Stark and additional toluene (6 mL) was added to the reaction flask. Over the course of the reaction the color became a clear, dull yellow color. After 7.5 h, the reaction was stopped and it was cooled to rt. Excess solvent and starting materials were removed by distillation (5mm Hg at 100 C) leaving ethyl 3-ethoxy-2-nitrobut-2-enoate (5.46 g) as an orangeliquid. An orange solution of 3-chloro-2-fluoroaniline (5.86 g, 40.2 mmol) and ethyl 3- ethoxy-2-nitrobut-2-enoate (5.45 g, 26.8 mmol) in ethanol (13.41 mL) was stirred at a After 7 h, the reaction was stopped and concentrated to give an orange oil. The orange oil was diluted with EtOAc and washed with 1.0 N HC1 (2x), saturated NaHCO3, brine, driedover sodium sulfate, filtered and concentrated to give an orange oil. Purification by normal phase chromatography gave Intermediate 24A1 (2.90 g, 36%) as a viscous orange-yellow oil. ?HNMR indicated a 1:1 E:Z mixture. MS(ESI)m/z: 325.0 (M+H)t ?H NMR (500 MHz, CDC13) oe 11.54 (br. s., 1H), 10.77 (br. s., 1H), 7.50 – 7.45 (m, 1H), 7.44 – 7.38 (m, 1H), 7.24 – 7.12 (m, 4H), 4.39 (q, J 7.2 Hz, 2H), 4.34 (q, J 7.2 Hz,2H), 2.15 (d,J 1.4 Hz, 3H), 2.12 (d,J 1.4 Hz, 3H), 1.39 (t,J 7.2 Hz, 3H), 1.36 (t,J7.0 Hz, 3H).

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PABBISETTY, Kumar Balashanmuga; CORTE, James R.; DILGER, Andrew K.; EWING, William R.; ZHU, Yeheng; (178 pag.)WO2017/19819; (2017); 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. 2106-04-9, name is 3-Chloro-2-fluoroaniline, A new synthetic method of this compound is introduced below., name: 3-Chloro-2-fluoroaniline

Step 1: Synthesis of 1-(2-amino-4-chloro-3-fluorophenyl)-2-chloroethan-1-one (2) To a stirred solution of AlCl3 (10.0 g, 75.01 mmol) and BCl3 (1M in n-hexane) (74 mL, 75.01 mmol) in CH2Cl2 (80 mL) was added 3-chloro-2-fluoroaniline 1 (9.0 g, 6.18 mmol) followed by a solution of chloroacetonitrile (11.6 g, 153.64 mmol) in CH2Cl2 (20 mL) at 0 C. under inert atmosphere. The reaction mixture was allowed to stir at RT for 30 minutes; heated to reflux temperature and maintained for additional 14 h. The reaction mixture was then cooled to 0 C., added aqueous 3N HCl solution (100 mL) and raised the temperature to reflux and stirred for 3 h. After completion of the reaction by TLC, the reaction mixture was cooled RT, diluted with water (50 mL) and extracted with CH2Cl2 (2*150 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure to obtain the crude. The crude was purified by triturating with n-pentane to afford compound 2 (4.5 g, 33%) as an off-white solid. 1H NMR (500 MHz, DMSO-d6): delta 7.61 (d, J=9.0 Hz, 1H), 7.35 (br s, 2H), 6.72 (d, J=9.0 Hz, 1H), 5.06 (s, 2H).

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

Reference:
Patent; PHARMAKEA, INC.; Evans, Jillian Frances; US9051320; (2015); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2106-04-9, name is 3-Chloro-2-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 2106-04-9, SDS of cas: 2106-04-9

A round bottom flask was charged with 1 eq of 3-chloro-2-fluoroaniline (3A), 1- methyl-2-pyrrolidinone (about 1.5 M 3 A in NMP), 2.2 eq of sodium cyanide, and 1.35 eq of nickel(II) bromide at RT under N2. The concentration was halved by the introduction of additional NMP under -N2 and the solution was gently warmed to 200+ 5C and stirred for 4 days under N2. The reaction mixture was allowed to cool to room temperature. The reaction mixture was diluted with 30 volumes of tert-butyl methyl ether (MTBE) and filtered through celite. The celite pad was then rinsed with 10 volumes of MTBE. The organics were washed with 40 volumes of brine, 2 x 40 volumes of water and 40 volumes of brine. The combined organics were dried over sodium sulfate and concentrated to afford a brown solid, which was dried under vacuum (-30 in Hg) at 400C for 8 hours to afford the compound of Formula 3B (71% yield).

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, 3-Chloro-2-fluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CYTOKINETICS, INC.; WO2007/75377; (2007); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2106-04-9, name is 3-Chloro-2-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 2106-04-9, Safety of 3-Chloro-2-fluoroaniline

Step 1: 6-Acetoxy-4-(3-chloro-2-fluoroanilino)-7-methoxycluinazoline hydrochloride6-Acetoxy-7-methoxyquinazolin-4-one (International Patent Application WO 96/15118, Example 39 thereof; 21.4 kg, 89.3 mol) was suspended in toluene (150 kg). To this was added N-ethyldiisopropylamine (13.3 kg, 103 mol). The brown suspension was heated to 70 C. then phosphorus oxychloride (36.0 kg, 228 mol) was charged. The reaction mixture was stirred at 70 C. for 5 hours. Further toluene (84.0 kg) was added followed by 3-chloro-2-fluoroaniline (14.88 kg, 102 mol). The reaction mixture was stirred at 70 C. for 2 hours during which time a solid precipitated. The suspension was cooled to 25 C. and held at this temperature for 93 hours. The reaction mixture was filtered and the filter cake washed with toluene (2×55.5 kg). The cake was further washed with a mixture of ethanol (24.5 kg) and water (32.0 kg) twice, then ethanol (50.5 kg) twice and the solid then dried under vacuum to give the title product as a beige solid (33.4 kg, 78%); 1H NMR: 2.37 (s, 3H), 4.00 (s, 3H), 7.34 (ddd, 1H), 7.48 (s, 1H), 7.52 (ddd, 1H), 7.61 (ddd, 1H), 8.62 (s, 1H), 8.86 (s, 1H); Mass Spectrum: 362.4, 364.4.

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, 3-Chloro-2-fluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; US2009/286982; (2009); 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. 2106-04-9, name is 3-Chloro-2-fluoroaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 3-Chloro-2-fluoroaniline

General procedure: N,N-Carbonyldiimidazole (0.17 g, 1.2 mmo1) was added to a solution of 8 (0.21 g, 1 mmo1) in anhydrous tetrahydrofuran (THF) and the mixture was stirred for 10 min at room temperature under a nitrogen atmosphere. Subsequently, substituted aniline or phenylethylamine (1.2 mmol) was slowly added to the mixture. The mixture was stirred at 80 oC overnight, then filtrated. The filtrate was evaporated under reduced pressure to give an oil or colored solid, which was purified by column chromatography with petroleum ether/ethyl acetate (7 : 1) to obtain the desired product 9a-9g.

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:
Article; Liu, Yang; Li, Yijing; Liu, Jianzhen; Yang, Limin; Li, Pengzhan; Zhao, Guisen; Letters in drug design and discovery; vol. 13; 4; (2016); p. 314 – 323;,
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. 2106-04-9, name is 3-Chloro-2-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H5ClFN

[00387] Intermediate 32A. (E)-N’-(3-Chloro-2-fluorophenyl)-2- oxopropanehydrazonoyl chloride: To a solution of 3-chloro-2-fluoroaniline (1.511 mL, 13.74 mmol) in HCl (116 mL, 116 mmol) at 0 C was added a solution of sodium nitrite (1.896 g, 27.5 mmol) in water (12 mL) dropwise while maintaining the temperature at 0 C. After completion of addition, the reaction was stirred at the same temperature for additional 30 mins. The pH of the reaction mixture was adjusted to 4.5 using solid sodium acetate. The resultant mixture was then treated dropwise with 3-chloropentane- 2,4-dione (2.129 mL, 17.86 mmol) in methanol (12 mL). After completion of addition, the reaction mixture was allowed to warm to room temperature and stirred at room temperature overnight. The reaction mixture was diluted with water and then extracted with ether. The crude product was then purified by silica gel chromatography to isolate the desired product. MS(ESI) m/z: 249.0 (M+2H)+.

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 2106-04-9.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PINTO, Donald J.; CORTE, James R.; GILLIGAN, Paul J.; FANG, Tianan; SMITH II, Leon M.; WANG, Yufeng; YANG, Wu; EWING, William R.; WO2013/22818; (2013); 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. 2106-04-9, name is 3-Chloro-2-fluoroaniline, A new synthetic method of this compound is introduced below., SDS of cas: 2106-04-9

Process step J+K, After 20 min at 50-60 C 1733 g 3-chloro-2-fluoranilin are added to the mixture. The dropping funnel is rinsed with 2 L acetonitrile. Then 7.8 kg 4 M hydrochloric acid in dioxane are added and the mixture is stirred for 45 mm at 55-80 C. After cooling to 1 C. the precipitate is filtered off and washed with 10 L ethanol. The precipitate is suspended in 40 L ethanol and combined with 290 g 3-chloro-2-fluoroaniline. The suspension is stirred for 45 min at 70-80 C and then for 13 h at RT. The precipitate is filtered off and washed with 10 L ethanol. After drying at 60 C in vacuo 4853 g of product is obtained as the hydrochloride.

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; OSTERMEIER, Markus; SIEGER, Peter; WO2014/12859; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2106-04-9, name is 3-Chloro-2-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 2106-04-9, Recommanded Product: 2106-04-9

Intermediate 32A. Ethyl 3-((3-chloro-2-fluorophenyl)amino)-2-nitrobut-2-enoate: Using a modified procedure described by Gomez-Sanchez. (Reference: Gomez-Sanchez, A. et al, Anales De Quimica, 81(2): 139 (1985)) A clear, faint yellow solution of ethyl nitroacetate (4.17 mL, 37.6 mmol) and triethylorthoacetate (6.93 mL, 37.6 mmol) in toluene (9.39 mL) was heated to 1 10 C. A Dean-Stark trap was used to azeotrope the ethanol. Approximately every 30 min, the solvent was removed from the Dean-Stark and additional toluene (6 mL) was added to the reaction flask. Over the course of the reaction the color became a clear, dull yellow color. After 7.5 h, the reaction was stopped and it was cooled to room temperature. Excess solvent and starting materials were removed by distillation (5 mm Hg at 100 C) leaving ethyl 3-ethoxy-2-nitrobut-2-enoate (5.46 g) as an orange liquid. An orange solution of 3-chloro-2-fluoroaniline (5.86 g, 40.2 mmol) and ethyl 3-ethoxy-2-nitrobut-2-enoate (5.45 g, 26.8 mmol) in ethanol (13.41 mL) was stirred at room temperature. After 7 h, the reaction was stopped and concentrated to give an orange oil. The orange oil was diluted with EtOAc and washed with 1.0 N HC1 (2*), saturated aHC03, brine, dried over sodium sulfate, filtered and concentrated to give an orange oil. Purification by normal phase chromatography gave Intermediate 32A (2.90 g, 36%) as a viscous orange-yellow oil. XH NMR indicated a 1 : 1 E:Z mixture. MS (ESI) m/z: 325.0 (M+H)+.

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; BRISTOL-MYERS SQUIBB COMPANY; PINTO, Donald J.P.; CLARK, Charles G.; SMITH, II, Leon M.; ORWAT, Michael J.; JEON, Yoon; CORTE, James R.; WO2014/160668; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics