Category: 1003-99-2

Adding a certain compound to certain chemical reactions, such as: 1003-99-2, name is 2-Bromo-5-fluoroaniline, belongs to bromides-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 1003-99-2, HPLC of Formula: C6H5BrFN

General procedure: Method I. Compounds 1a-1e and 3b were synthesized using a modified procedure.1 Substituted aniline (1.0 equiv.) was added to a round-bottom flask. The flask was fitted with a rubber septum and purged with nitrogen gas, and acetic anhydride (1M in CH2Cl2, 1.1 equiv.) was added at room temperature. The reaction was refluxed overnight and monitored by TLC. Upon completion the reaction mixture was quenched with H2O. The resulting mixture was extracted with CH2Cl2. The combined organic layers were washed with brine, dried over anh. Na2SO4, filtered, then concentrated in vacuo to give the product.

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

Reference:
Article; Lasing, Thitiya; Phumee, Atchara; Siriyasatien, Padet; Chitchak, Kantima; Vanalabhpatana, Parichatr; Mak, Kit-Kay; Hee Ng, Chew; Vilaivan, Tirayut; Khotavivattana, Tanatorn; Bioorganic and Medicinal Chemistry; vol. 28; 1; (2020);,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 1003-99-2, name is 2-Bromo-5-fluoroaniline, molecular formula is C6H5BrFN, 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. Quality Control of 2-Bromo-5-fluoroaniline

2-Bromo-5- fluorobenzenamine (15 g, 78.94 mmol) was weighed into a 100 mL flask and dissolved in 100 mL of 6N HCl. The reaction mixture was heated to reflux, followed by dropwise addition of (E)-but-2-enal (6.87 ml, 83 mmol) mixed with 1.0 mL deionized water over 25 minutes. Following complete addition, the reaction was heated at 100 °C for an additional 35 minutes. The reaction was cooled to ambient temperature, followed by addition of 50 mL of Et2O. The reaction was stirred for 5 minutes followed by removal of Et2O by separatory funnel. ZnCl2 (3.587 g, 26 mmol) was added to the aqueous layer in two portions and the reaction mixture was cooled to 0 0C over 30 minutes. The aqueous layer was then taken to pH 8.0 using concentrated NH4OH. The aqueous layer was then extracted with Et2O and then EtOAc. The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo, affording the desired product 8-bromo-5-fluoro-2-methylquinoline (18.1 g, 95 percent yield) as a solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1003-99-2, its application will become more common.

Reference:
Patent; ARRAY BIOPHARMA INC.; WO2008/121687; (2008); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 1003-99-2, name is 2-Bromo-5-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1003-99-2

2-Bromo-5-fluoro-N-(propan-2-yl)aniline E-1.7″” ‘ 2-bromo-5-fluoroaniline E-1.7″”” (2.00 g; 10.53 mmol) is suspended in 20 ml DCM and propan-2-one (1.55 ml; 21.05) is added and the reaction mixture is stirred for 16 at 20°C. Afterwards sodium triacetoxyborohydride (4.69 g; 21.05 mmol) is added and the reaction mixture is stirred for 48h at 20 °C. The reaction mixture is poured into water and extracted with DCM. The combined organic layer is dried over MgS04 the solid materials are filtered off and HCl in dioxane is added until the pH value is below 2. The solvents are concentrated under reduced pressure. The crude product is purified using reversed phase chromatography (Method: prep. HPLC1). Product containing fractions are combined and extracted with DCM. To the organic layer HCl in dioxane is added until the pH value is below 2. The solvents are concentrated under reduced pressure. Yield 91percent (2.57 g; 9.58 mmol) HPLC-MS: tRet = 1.09 min; method VAB

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 1003-99-2.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ENGELHARDT, Harald; WO2015/169962; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 1003-99-2, name is 2-Bromo-5-fluoroaniline, belongs to bromides-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 1003-99-2, Safety of 2-Bromo-5-fluoroaniline

N-(2-Bromo-5-fluorophenyl)pivalamide. Trimethylacetyl chloride (4.2 mL, 34.1 mL) was fast dropwise added to a solution of 2-bromo-5-fluorobenzenamine (4.31 g, 22.7 mmol) in CH2Cl2 (50 mL) at room temperature, followed by the addition of DIEA (7.9 mL, 45.4 mmol). The resulting mixture was stirred at room temperature for 2 hrs, and then partitioned between HCl (1N, 200 mL) and EtOAc (250 mL). After separation, the organic phase was washed with brine (50 mL), dried on MgSO4, concentrated on rotary vacuum, and purified on flash chromatography eluting with 2040percent EtOAc/hexanes (1200 mL) to afford the expected product, as a colorless oil (6.07 g, 98percent yield); 1H NMR (400 MHz, CDCl3) delta ppm 1.33 (s, 9H), 6.69 (ddd, J=8.81, 7.55, 3.02 Hz, 1H), 7.45 (dd, J=8.81, 5.79 Hz, 1H), 8.04 (s, 1H), 8.28 (dd, J=11.08, 3.02 Hz, 1H); Mass spec. 274.04 (MH+), Calc. for C11H13BrFNO 273.02

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-Bromo-5-fluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chaturvedula, Prasad V.; Mercer, Stephen E.; Fang, Haiquan; US2006/94707; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 1003-99-2, 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. 1003-99-2, name is 2-Bromo-5-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2-bromo-5-fluoroaniline (1.0 eq.) in tetrahydrofuran (0.2 M) at O0C under N2 atmosphere was added dropwise IM NaHMDS (2.5 eq.) The reaction was stirred for 15 minutes at 00C, and a solution of di-tert -butyl dicarbonate in tetrahydrofuran was added. The reaction was warmed to room temperature overnight. The solvent was evaporated, and the resulting residue was quenched with 0.1N HCl aqueous solution. The aqueous suspension was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vacuo. The crude material was purified by flash chromatography on a COMBIFLASH.(R). system (ISCO) using 0-5percent ethyl acetate in hexane to give the product as light yellow oil.

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-5-fluoroaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; IRM LLC; NOVARTIS AG.; WO2009/111337; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 1003-99-2,Some common heterocyclic compound, 1003-99-2, name is 2-Bromo-5-fluoroaniline, molecular formula is C6H5BrFN, 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 la. 3-Fluorophenanthridin-6-ol1 aA mixture of 2-(ethoxycarbonyl)phenylboronic acid (7.0 g, 39 mmol), 2-bromo-5- fluoroaniline (7.4 g, 39 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (S- Phos, 0.32 g, 0.78 mmol), sodium acetate (4.1 g, 39 mmol), and palladium acetate (0.087 g, 0.39 mmol) in 18 ml. of ethanol was heated with stirring at 80° C for 18 h. Additional 2- (ethoxycarbonyl)phenylboronic acid (2.0 g), S-Phos (0.095 g), palladium acetate (0.020 g), and sodium carbonate (1.2 g) was added and the mixture was stirred for 18 h. The solvent was removed by evaporation under reduced pressure, and the resulting solid was isolated by vacuum filtration, washing the remaining solid with water and then hexane. The remaining solid and dried in vacuo @ 50° C to provide the title compound (4.39 g, 53percent yield) which was used without further purification.

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

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; ABBOTT LABORATORIES; MCDANIEL, Keith, F.; CHEN, Hui-ju; SHANLEY, Jason, P.; GRAMPOVNIK, David, J.; GREEN, Brian; MIDDLETON, Timothy; HOPKINS, Todd; OR, Yat, Sun; WO2012/92411; (2012); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 1003-99-2, name is 2-Bromo-5-fluoroaniline, A new synthetic method of this compound is introduced below., Formula: C6H5BrFN

EXAMPLE 4 2-(2-amino-4-fluorophenyl)-3-methyl-2-cyclopenten-1-one 4.937 g (25.982 mmol) of 2-bromo-4-fluoroaniline, 4.00 g (28.584 mmol) of 5-methyl-1-cyclopenten-2-one boronic acid compound, 0.30 g (0.260 mmol) of tetrakis(triphenylphosphine)palladium, and 4.13 g (38.978 mmol) of sodium carbonate were loaded to 250 mL schlenk flask, and then 80 mL of degassing DME and 27 mL of H2O that had been purged with N2 were added thereto using a syringe. The mixture was reacted at 90° C. for 12 hours. The work-up was the same as in Example 3 (3.84 g, 72percent). 1H NMR (CDCl3): =6.83 (t, J=7.6 Hz, 1H, Ph), 6.48 (t, J=7.6 Hz, 1H, Ph), 6.43 (d, J=10.4 Hz, 1H, Ph), 3.82 (br s, 2H, NH2), 2.73-2.71 (m, 2H, CH2CP), 2.58-2.55 (m, 2H, CH2Cp), 2.09 (s, 3H, CH3); 13C {1H} NMR (CDCl3): =207.93, 175.26, 168.18(d, J=242.6 Hz, PhC-F) 146.47(d, J=5.7 Hz, Ph), 138.76, 131.90(d, J=9.8 Hz, Ph), 113.71, 105.08(d, 22 Hz, Ph), 102.91 (d, 22 Hz, Ph), 34.79, 32.22, 18.63

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; LG Chem, Ltd.; US7538239; (2009); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 1003-99-2, name is 2-Bromo-5-fluoroaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Bromo-5-fluoroaniline

Example 29 : 6- (2-Bromo-5-fluoro-phenylamino)-4-cyclopropyl-N- (tetrahydro-pyran-4- ylmethyl)-nicotinamide; A mixture of 6-chloro-4-cyclopropyl-N- (tetrahydro-pyran-4-ylmethyl)-nicotinamide (Description 3) (100 mg), 2-bromo-5-fluoroaniline (65 mg), cesium carbonate (155 mg), tris (dibenzylidene- acetone) palladium (0) (3. 3 mg), 4,5-bis (diphenylphosphino) -9,9-dimethyl xanthene (Xantphos) (2.2 mg) and 1,4-dioxan (1 ml) was stirred under reflux under nitrogen for 18 hours. The mixture was allowed to cool, the insoluble material filtered off, and washed with ethyl acetate. The filtrate was evaporated under reduced pressure and the residue purified by MDAP to afford the title compound as a pale cream solid (14 mg). NMR (DMSO-d6) 8 0.73 (2H, m), 1.02 (2H, m), 1.12-1. 27 (2H, m) 1.62 (2H, d), 1.77 (1H, m), 2.34 (1H, m), 3.13 (2H, t), 3.27 (2H, t), 3.85 (2H, d of d), 6.69 (1H, s), 6.81 (1H, t of d), 7.63 (1H, t), 8.09 (1H, m), 8.11 (1H, s), 8.31 (1H, s), 8.38 (1H, t). LC/MS t = 3.1 min, [MH+] 448 consistent with the molecular formula C2lH237 BrFN302.

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; GLAXO GROUP LIMITED; WO2005/75464; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 1003-99-2, name is 2-Bromo-5-fluoroaniline, belongs to bromides-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 1003-99-2, Quality Control of 2-Bromo-5-fluoroaniline

2-Azido-l-bromo~4-fluorobenzene. 2-Bromo-5-fluoro aniline (2.00 g, 10.53 mmol) was dissolved in concentrated HCl (10 mL) and water (10 mL) and cooled to 0 °C. Aqueous NaNO2 solution (1.090 g, 15.8 mmol OfNaNO2 in 10 mL of water) was added dropwise at such a rate that the temperature did not exceed 5°C. This mixture was stirred at 00C for 1.5 h. A solution OfNaN3 (1.027 g, 15.8 mmol) and NaOAc (12.95 g, 158 mmol) in water (50 rnL) was then added at 0-5°C and the mixture was stirred for an additional Ih at this temperature. The mixture was extracted with ethyl acetate and the combined extracts were washed with brine and dried over Na2SO4. The filtrate was concentrated to afford the title compound as a tan solid (2.188 g, 96percent): 1H NMR (400 MHz, CDCl3): 7.53 (1 H, dd, J=8.8, 5.6 Hz), 6.94 (1 H, dd, J=8.8, 2.8 Hz), 6.79 (1 H, ddd, J=8.8, 7.6, 2.8 Hz).

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/64316; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 1003-99-2, These common heterocyclic compound, 1003-99-2, name is 2-Bromo-5-fluoroaniline, 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.

The N-(t-butyloxycarbonyl)-4-piperidone (10.13 g, 50.8 mmol, 1.0 eq) and the 2-bromo-5-fluoroaniline (11.6Og, 61.0 mmol, 1.2 eq.) were weighed into a flask. Acetic acid (75 mL) was added, followed by trimethylsilyl cyanide (7.75 mL, 58.1 mmol, 1.14 eq.). The mixture was stirred at rt for 24 hr, and was then added to a mixture of 200 mL ice and 200 mL saturated ammonium hydroxide solution. The resulting mixture was extracted twice with methylene chloride, and the organic solution was dried over magnesium sulfate, filtered, and concentrated to provide 22.57g of crude product.

Statistics shows that 2-Bromo-5-fluoroaniline is playing an increasingly important role. we look forward to future research findings about 1003-99-2.

Reference:
Patent; MERCK & CO., INC.; SUNESIS PHARMACEUTICALS, INC.; WO2006/44497; (2006); A2;,
Bromide – Wikipedia,
bromide – Wiktionary