Category: 116557-46-1

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. 116557-46-1, name is 3-Bromo-2-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 3-Bromo-2-methoxyaniline

Step 3[00174j IntlO (2.0 g, 9.9 mmol) was dissolved in dioxane (40 mL) and the vessel purged with nitrogen for 5 minutes. Next bis(pinacolato)diborone (3.77 g, 14.85 mmol), [1,1 ?-bis(diphenylphosphino)ferrocene] dichloropalladium (II) complex with dichloromethane (404 mg, 0.49 mmol) and potassium acetate (2.91 g, 29.7 mmol) were added. The flask was evacuated and backfilled with nitrogen, and then heated to 100 Cfor 15 hours. Water was added to quench the reaction and the product was then extracted with EtOAc. The combined organic layers were washed with brine (x3), dried over sodium sulfate, filtered, concentrated and purified using automated chromatography (elutes at 40% ethyl acetate) to provide Intl 1 (2.0 g, 8 1%). ?H NMR (400MHz, chloroform-d) oe 7.12 (dd,J=7.3, 1.8 Hz, 1H), 6.96-6.89 (m, 1H), 6.88-6.83 (m, 1H),3.82 (s, 3H), 1.37 (s, 12H). LC retention time 0.65 [J]. m/z: 250 (MHj.

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 116557-46-1.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MOSLIN, Ryan M.; WEINSTEIN, David S.; WROBLESKI, Stephen T.; TOKARSKI, John S.; KUMAR, Amit; WO2014/74661; (2014); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 116557-46-1,Some common heterocyclic compound, 116557-46-1, name is 3-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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 mixture of 3-bromo-2-methoxyaniline (3 g), 3-carboxyphenylboronic acid (2.94 g), bis(triphenylphosphine)palladium(II)chloride [PdCl2(PPh3)2] (0.30 g) and potassium carbonate (5.2 g) in ethanol (100 mL) and water (20 mL) was heated to about reflux temperature and stirred for about 28 hours. The hot mixture was filtered to remove the catalyst. The clear filtrate was concentrated under vacuum. To the residue, water (50 mL) and methanol (50 mL) was added, acidified to pH 3-5 using hydrochloric acid and stirred for about 30 minutes at about room temperature. The slurry was filtered, washed with n-hexane (50 mL) and dried in an oven at about 55 C. to about 60 C. for about 12 hours. Yield: 1.8 g 1H NMR (300 MHz in DMSO-d6): delta 8.08 (s, 1H), 7.89-7.92 (d, 1H), 7.73-7.75 (d, 1H), 7.51-7.56 (t, 1H), 6.87-6.92 (t, 1H), 6.72-6.74 (d, 1H), 6.50-6.53 (d, 1H), 3.27 (s, 3H)

The synthetic route of 116557-46-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Glenmark Generics Limited; Upadhye, Bhargav Krishnaji; Jagadale, Shivaji Eknath; Soni, Mukesh; US2015/87845; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 116557-46-1, name is 3-Bromo-2-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 3-Bromo-2-methoxyaniline

[00238j To a reaction vial charged with 3-bromo-2-methoxyaniline (1.12 g, 5.54mmol), 1 -methyl-4-(4,4,5 ,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- 1 H-pyrazole (1.499 g,7.21 mmol) in dioxane (6 mL) was added aqueous potassium phosphate (2.0 M) (5.54 ml,11.09 mmol). The resulting mixture was deoxygenated by bubbling argon through themixture for 5 minutes. [1,1 ?-Bis(diphenylphosphino)ferrocene] dichloropalladium(II)(PdC12(dppf), 0.122 g, 0.166 mmol) was then added and the mixture was heated at 110 Cfor 2 hours. The reaction was cooled, diluted with ethyl acetate (200 mL), washed with water, brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford tan oil as the crude product mixture. This material was purified by silica gel flash chromatography using hexanes/ethyl acetate mixtures as the eluent. Fractions containingthe desired product were collected, combined, and concentrated under vacuum to afford0.87 g (77%) of the desired product as an oil which solidified upon standing. HPLC (Method N) = 0.89 minutes. LCMS MH+ 204.1.

According to the analysis of related databases, 116557-46-1, the application of this compound in the production field has become more and more popular.

116557-46-1, name is 3-Bromo-2-methoxyaniline, belongs to ethers-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 116557-46-1

To a solution of 3-bromo-2-methoxyaniline (20 g) in 1N hydrochloric acid (400 mL) was added a solution of sodium nitrite (7.2 g in 720 mL of water) at about 0 C. to about 5 C. under stirring. The reaction mixture was stirred for about 15 minutes at about 5 C. Then ethyladetoacetate (12.9 g) was added to the reaction mixture and stirred for about 15 minutes at about 0 C. to about 5 C. Sodium bicarbonate solution (27.5 g in 300 mL water) and ethanol (400 mL) was then added to the reaction mixture. The reaction mixture was allowed to warm to about room temperature and stirred for about 2 hours. The mixture was filtered, washed with water (200 mL) and dried to get yellowish solid. Yield: 33 g; Melting point: 75.9-77.1 C.; Purity (HPLC): 99.12% IR: 3421, 1706, 1684, 1517, 1215, 1093, 980 cm-1; Mass: m/z 342.88 [M+] and 344.86 [M+2] 1H NMR (300 MHz in CDCl3): delta 12.86 (s, 1H), 7.58-7.61 (d, 1H), 7.30-7.33 (d, 1H), 7.02-7.07 (m, 1H), 4.31-4.43 (q, 2H), 3.95 (s, 3H), 2.5 (s, 3H), 1.38-1.43 (t, 3H)

The synthetic route of 116557-46-1 has been constantly updated, and we look forward to future research findings.

Adding a certain compound to certain chemical reactions, such as: 116557-46-1, name is 3-Bromo-2-methoxyaniline, belongs to ethers-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 116557-46-1, Recommanded Product: 116557-46-1

[00239] 3-Bromo-2-methoxyaniline (500 mg, 2.47 mmol), bis(pinacolato)diboron (755 mg,2.97 mmol) and potassium acetate (728 mg, 7.42 mmol) were mixed in 1,4-dioxane (8 mL) and nitrogen gas was blown through for 5 minutes. 1,1-Bis(diphenyl-phosphino)ferrocene- palladium(ll)dichloride DCM adduct (173 mg, 0.21 mmol) was added and nitrogen blown through again. The mixture was heated under reflux conditions for 2.5 hours then allowed to cool (black mixture). Dl water and DCM were added (35mls of each) and the mixture wasstirred vigourously for 30 minutes then passed through a hydrophobic frit. The DCM phase was concentrated down to remove excess Dioxane then redissolved in minimum DCM and was purified by flash chromatography eluting with 0-100% ethyl acetate/isohexane over 40 minutes. Product containing fractions were concentrated down to give 2-methoxy-3-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)aniline as an off-white solid 358mg. [00240] 1H NMR (DMSO-d6): O 6.88 (m, 3H), 4.80 (bs, 2H), 3.64 (5, 3H), 1.29 (5, 12H).

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

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; GOLDBERG, Kristin; HAMILTON, Niall; JONES, Stuart; JORDAN, Allan; LYONS, Amanda; NEWTON, Rebecca; OGILVIE, Donald; WASZKOWYCZ, Bohdan; WO2015/79251; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 116557-46-1, 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. 116557-46-1, name is 3-Bromo-2-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 3 A solution of 3-bromo-2-methoxyaniline from Step 2 (1.94 g, 9.60 mmol), 4,4,445,5,55′-octamethyl-2,2′-bi(l,3,2-dioxaborolane) (3.66 g, 14.40 mmol), PdCl2(dppf)-CH2Cl2 complex (0.392 g, 0.480 mmol) and potassium acetate (2.83 g, 28.8 mmol) in dioxane (32 mL) in a flask was heated to reflux (-100 C) overnight then cooled to room temperature, concentrated in vacuo on CELITE. This crude product was purified by flash chromatography using a 120g silica gel column (solid loading) eluting with 0-50% ethyl acetate/hexanes. Appropriate fractions (eluted near 25% EtOAc/hexanes) were collected and concentrated in vacuo to give 2-methoxy-3-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)aniline (1.47 g, 5.78 mmol, 60.2% yield) as a crystalline off-white solid. LCMS MH+ 250.1.

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-Bromo-2-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MOSLIN, Ryan M.; WEINSTEIN, David S.; WROBLESKI, Stephen T.; ZHANG, Yanlei; TOKARSKI, John S.; MERTZMAN, Michael E.; LIU, Chunjian; WO2015/69310; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 116557-46-1, A common heterocyclic compound, 116557-46-1, name is 3-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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.

Preparation 10 To a reaction vial charged with 3-bromo-2-methoxyaniline (from Step 4 of Preparation 9, 1.12 g, 5.54 mmol), l-methyl-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)-lH-pyrazole (1.499 g, 7.21 mmol) in dioxane (6 mL) was added aqueous potassium phosphate (2.0 M) (5.54 ml, 11.09 mmol). The resulting mixture was deoxygenated by bubbling argon through the mixture for ~5 min. PdCl2(dppf) (0.122 g, 0.166 mmol) was then added and the mixture was heated at 110 C for 2h. The reaction was cooled, diluted with EtOAc (200 mL), washed with water, brine, dried over anhyd sodium sulfate, filtered and concentrated to afford tan oil as the crude product mixture. This material was purified by silica gel flash chromatography using hexanes/ethyl acetate mixtures as the eluant. Fractions containing the desired product were collected, combined, and concentrated under vacuum to afford 0.87 g (77%) of the desired product (Preparation 10) as an oil which solidified upon standing. HPLC (method N) = 0.89 min. LCMS MH+ 204.1.

The synthetic route of 116557-46-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MOSLIN, Ryan M.; WEINSTEIN, David S.; WROBLESKI, Stephen T.; ZHANG, Yanlei; TOKARSKI, John S.; MERTZMAN, Michael E.; LIU, Chunjian; WO2015/69310; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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 116557-46-1 as follows. category: ethers-buliding-blocks

(E)-N-(3-Bromo-2-methoxyphenyl)-3-ethoxyacrylamide (3c); A mixture of 3-bromo-o-anisidine (2c) (4.50 g, 22.3 mmoles) and pyridine (15 mL) was placed in an icebath. (E)-3-ethoxy-2-propenoyl chloride (1) (3.75 g, 27.9 mmol) was added dropwise as the solution stirred continuously for one hour. The mixture was concentrated to remove the pyridine and was transferred to a seperatory funnel where AcOEt and water were added. Concentrated HCl was added until the aqueous layer was pH 1. The water layer was extracted twice with AcOEt and the organic layers were washed with saturated NaCl (25 mL) containing 1 M HCl (2 mL). The procedure was followed by a second wash of saturated NaCl (25 mL) containing saturated NaHCO3 (5 mL). The organic layer was finally washed with saturated NaCl (25 mL). The product layer was dried and filtered through silica gel (2) using a solvent system of 1:1 followed by 2:1 hexanes-AcOEt. The product was chromatographed (2:1 1:1 hexanes:AcOEt) and recrystalized from 10:1 hexanes-AcOEt to afford light brown-orange crystals (3.35 g, 50% yield): mp 102-104 C; 1H NMR (400 MHz, CDCl3) 8.35 (dd, J=8.4, 1.6 Hz, 1H), 7.65 (d, J=12.4 Hz, 1H), 7.52 (bs, 1H), 7.21 (dd, J=8.4, 1.6 Hz, 1H), 6.98 (t, J=8.4 Hz, 1H), 5.36 (d, J=12.0 Hz, 1H), 3.97 (q, J=7.2 Hz, 2H), 3.86 (s, 3H), 1.37 (t, J=7.2 Hz, 3H).

According to the analysis of related databases, 116557-46-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Horwitz, Jerome P.; Polin, Lisa; US2007/60612; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem