Category: 16618-68-1

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. 16618-68-1, name is 3-Bromo-5-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 3-Bromo-5-methoxyaniline

To a solution of 5-bromo-3-(2-fluoropyridin-4-yl)-4-methyl-1-tosyl-1H-pyrrolo[2,3-b]pyridine from step 3 (258 mg, 0.56 mmol) in 1,4-dioxane (5 mL) was added potassium acetate (165 mg, 1.68 mmol), bis(pinacolato) diboron (569 mg, 2.24 mmol) and bis(diphenylphosphino)ferrocene]dichloropalladium(II).DCM (23 mg, 0.028 mmol). The solution was treated with microwave radiation at 130 C. for 3.5 hours. To this solution was added 3-bromo-5-methoxyaniline (113 mg, 0.56 mmol), potassium carbonate (232 mg, 1.68 mmol) and bis(diphenylphosphino)ferrocene]dichloropalladium(II).DCM (23 mg, 0.028 mmol). The solution was treated with microwave radiation at 120 C. for one hour. After cooling the resulting solution was partitioned between ethyl acetate and water. The organic layer was washed with water, brine and dried over magnesium sulfate. The mixture was filtered and concentrated in vacuo. The crude material was purified using normal phase chromatography (ethyl acetate/heptane) to provide 3-(3-(2-fluoropyridin-4-yl)-4-methyl-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-5-methoxyaniline (154 mg, 55% yield): MS (ES) m/z 503 (M+H).

According to the analysis of related databases, 16618-68-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jacobsen, Eric Jon; Blinn, James Robert; Springer, John Robert; Hockerman, Susan L.; Anderson, David Randolph; (120 pag.)US2018/208594; (2018); A1;,
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Synthetic Route of 16618-68-1,Some common heterocyclic compound, 16618-68-1, name is 3-Bromo-5-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)..Prep aration o f .intermediate 34; A solution of butanoyl chloride (0.0292 mol) in DCM (10ml) was added dropwise to a solution of 3-bromo-5-methyloxybenzenamine (0.0292 mol) and Et3N (0.035 mol) in DCM (50ml) at 5C under N2 flow. The mixture was stirred at room temperature for 1 hour. K2CO3 10% was added and the organic layer was decanted, dried (MgSO4), filtered off and evaporated till dryness, yielding 8 g (100%) of intermediate 34.

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

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WO2009/53373; (2009); A1;,
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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 16618-68-1 as follows. HPLC of Formula: C7H8BrNO

c) A solution of the compound of Example 374(b) (1 g, 4.78 mmol, 1.2 eq.), 3-bromo-5-methoxyaniline (0.8 g, 3.98 mmol) and potassium fluoride (0.23 g, 3.98 mmol, 1 eq.) in DMF was heated at 120 C. for 12 h. The mixture was quenched and extracted as in Example 1(d). The solvent was distilled off to afford the crude residue which was purified by column chromatography (60-120 silica gel, 50% ethyl acetate in hexane) to give the product in 42% yield (0.81 g).

According to the analysis of related databases, 16618-68-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Linnanen, Tero; Wohlfahrt, Gerd; Nanduri, Srinivas; Ujjinamatada, Ravi; Rajagopalan, Srinivasan; Mukherjee, Subhendu; US2015/11548; (2015); A1;,
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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. 16618-68-1, name is 3-Bromo-5-methoxyaniline, A new synthetic method of this compound is introduced below., COA of Formula: C7H8BrNO

Step 1 : 4.0g (0.02 mol) of 3-Bromo-5-methoxy-aniline, 4.6 g (0.05 mol) of glycerol, 2.46g (0.02 mol) of nitrobenzene and 12 ml of 75% sulfuric acid were stirred for 3 h at 150C. After this dark solution was poured onto 100 g of crushed ice, 100 ml of ethylacetate (EtOAc) and 30 ml of 30% solution of NaOH. After 1 hour brown solid was filtered off and the organic layer was separated. After filtering through Si02 and evaporation of solvent 7-bromo-5- methoxy-quinoline and 5-bromo-7-methoxy-quinoline were separated as mixture approximately 60:40 (total 3.5g, 74%) This mixture was separated to individual 7-bromo-5- methoxy-quinoline and 5-bromo-7-methoxy-quinoline with column chromatography on silica-gel with benzene-EtOAc (3: 1) as eluent. Yield of pure 7-bromo-5-methoxy-quinoline was 950 mg (27% from mixture).

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; HOFFMANN, Matthias; BISCHOFF, Daniel; DAHMANN, Georg; KLICIC, Jasna; SCHAENZLE, Gerhard; WOLLIN, Stefan Ludwig Michael; CONVERS-REIGNIER, Serge Gaston; EAST, Stephen Peter; MARLIN, Frederic Jacques; MCCARTHY, Clive; SCOTT, John; WO2013/14060; (2013); A1;,
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Related Products of 16618-68-1,Some common heterocyclic compound, 16618-68-1, name is 3-Bromo-5-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.

Step 1 : Synthesis of N-(3-Bromo-5-methoxy-phenyl)acetamideTo a solution of 20 g of 3-bromo-5-methoxy-aniline in 200 mL DCM was added 27.44 mL triethylamine at 0 C .To the reaction mixture was added 7.06 mL acetyl chloride dropwise over 30 min. The reaction was stirred at 30C for 3 h, and then poured onto ice. The pH was adjusted to pH 7 with aqueous NaHC03 and the precipitated solids were removed by filtration. The aqueous was extracted with DCM and the combined organic extracts were dried over sodium sulfate, filtered and evaporated under reduced pressure to yield 20 g N-(3-bromo-5- methoxy-phenyl) acetamide as solid.Analysis: HPLC-MS: Rt = 2.44 min (method Q), M+H = 244 / 246

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; DAHMANN, Georg; HOFFMANN, Matthias; KLICIC, Jasna; LAMB, David James; MCCARTHY, Clive; NAPIER, Spencer; PARRISH, Karen; SCOTT, John; SWANTEK FITZGERALD, Jennifer L.; WALKER, Edward; WO2015/140054; (2015); A1;,
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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. 16618-68-1, name is 3-Bromo-5-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C7H8BrNO

To a mixture of aq. formaldehyde (37wt%, 4.47mL, 60.0mmol) in THF (15mL) and aq. H2SO4 (3.0molL-1, 4.00mL) in an open flask was added via dropping funnel a suspension of 3-bromo-5-methoxyaniline (3.03g, 15.0mmol) and NaBH4 (1.70g, 45.0mmol) in THF (15mL) over 1hat 15C±5C (inside temperature). After 30min of stirring, pH 8 was adjusted with aq. sat. Na2CO3 and concentrated in vacuo. The residue was diluted with water (80mL) extracted with CH2Cl2 (3×100mL). The combined organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was suspended with CH2Cl2, filtered and the filtrate was concentrated in vacuo to give 3-bromo-5-methoxy-N,N-dimethylaniline (7) as an orange oil (1.81g, 52%): Rf 0.81 (CH2Cl2 100%); numax (neat): 2935m, 2358w, 1604s, 1557s, 1495m, 1431m, 1358w, 1319w, 1276w, 1238m, 1149m, 1060m, 996m, 875w, 812w, 788m, 675w; 1H NMR (500MHz, CDCl3) delta=6.47 (1H, dd, 4J 2.2, 1.7, C2H); 6.42 (1H, dd, 4J 2.0, 1.7, C6H), 6.13 (1H, t, 4J 2.2, C4H), 3.77 (3H, s, OCH3), 2.92 (6H, s, N(CH3)2); 13C NMR (125MHz, CDCl3) delta=161.1 (C5), 152.3 (C3), 123.5 (C1), 108.6 (C2), 104.7 (C6), 97.7 (C4), 55.4 (OCH3), 40.4 (N(CH3)2); ESI-MS: m/z calcd. for C9H13NO+ 230.0175 found 230.0173 [M+H+].

The synthetic route of 16618-68-1 has been constantly updated, and we look forward to future research findings.

Adding a certain compound to certain chemical reactions, such as: 16618-68-1, name is 3-Bromo-5-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 16618-68-1, HPLC of Formula: C7H8BrNO

To a solution of 3-bromo-5-methoxyaniline (5.0 g, 25 mmol) stirred in acetone (100 mL) at room temperature, benzoyl isothiocyanate (3.95 mL, 27.2 mmol) was added. The reaction mixture was stirred for 1 hour before the acetone was removed by evaporation. The crude residue obtained was washed with hexanes and collected by filtration to give N-((3-bromo-5-ethoxyphenyl)carbamothioyl)benzamide as a yellow solid (8.0 g, 89 %). LC (Method B): 2.351 min. MS (APCI): calcd for Ci5Hi4BrN202S [M+H]+ m/z 365.0, 367.0, found 365.0, 367.0. 1H NMR (DMSO-d6, 400 MHz) 5 ppm 12.57 (br s, 1H), 11.64 (br s, 1H), 7.98 (d, J = 7.4 Hz, 2H), 7.67 (t, J = 7.4 Hz, 1H), 7.60 (br s, 1H), 7.55 (t, J = 7.8 Hz, 2H), 7.34 (br s, 1H), 7.08 (t, J = 2.0 Hz, 1H), 3.79 (s, 3H).

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

Related Products of 16618-68-1, 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. 16618-68-1, name is 3-Bromo-5-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 3-bromo-5-methoxyaniline (5.00 g, 24.746 mmol, 1.00 equiv) and K2CO3 (5.13 g, 37.119 mmol, 1.50 equiv) in acetone (100.00 ml_) was added ethyl bromoacetate (4.96 g, 29.695 mmol, 1.20 equiv). The resulting mixture was stirred at reflux for 3 days. The reaction mixture was filtered, and the filtrate was evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 30% EtOAc in petroleum ether. Pure fractions were evaporated to dryness to afford ethyl 2-[(3-bromo-5-methoxyphenyl)amino]acetate (1.8 g, 25.24%) as a yellow gum. LCMS (ESI) m/z: [M+H]+ = 288.

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

Reference:
Patent; FOGHORN THERAPEUTICS INC.; ZHOU, Qianhe; BOCKER, Michael; MILLAN, David, Simon; CHAN, Ho, Man; SOARES, Luis; NETHERTON, Matthew, Russell; RUPPEL, Sabine, K.; YANG, Zhaoxia; LOWE, Jason, T.; BRUCELLE, Francois; (220 pag.)WO2019/152440; (2019); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 16618-68-1, These common heterocyclic compound, 16618-68-1, name is 3-Bromo-5-methoxyaniline, 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.

In 50 ml by adding three-necked bottle 1.01g3-methoxy-5-bromoaniline(5mmol), 1.40g (5.5mmol) connecting boric acid frequency ester, 1.47g (15mmol) and potassium acetate PdCl2(dppf) catalyst (150 mg), vacuum pumping and nitrogen injection 6 times, the state of the protection of nitrogen by adding DMSO (25 ml), 80 C reaction 18h, in a water cooling retrodisplacement, precipitate after filtering, washing, drying to obtain the crude column chromatography separation (petroleum ether: ethyl acetate = 1:5) shall be 1.03g yellow powdery solid, yield 82.4%.The 0.99g the above-mentioned preparation of the compound (4mmol) by adding 100 ml round-bottom flask, add 30 ml of methanol is dissolved, add 0.56gNH4Cl (10mmol), constant voltage dropping funnel for slowly dripping 2.56gNaIO4(12mmol) of 7 ml aqueous solution, stirring the mixture at room temperature for reaction 18h, TLC detection, filtering to remove the inorganic salt, methanol filters after evaporation to dryness, drying to obtain the crude product purification column chromatography (petroleum ether: ethyl acetate = 1:5) shall be near white powdery solid 0.53g, yield 79.1%.

The synthetic route of 16618-68-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ocean University of China; Jiang, Tao; Yin, ruijuan; Zhang, Li Juan; (38 pag.)CN103497211; (2016); B;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 16618-68-1, 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 16618-68-1 as follows.

4.1.2. Synthesis of 5-hydroxy-7-bromo-quinoline from Scheme 2[0119]The title compound can be purchased by Shanghai Haoyuan Chemexpress Co., Ltd. CHINA or synthesized via known 3-bromo-5-methoxyaniline (Liedholm, Brita. Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry (1984), B38(10), 877-84 or Hodgson, H. H.; Wignall, J. S Journal of the Chemical Society (1926)) in two steps. 3-Bromo-5-methoxy-aniline, 4.6 g (0.05 mol) of glycerol, 2.46 g (0.02 mol) of nitrobenzene and 12 ml of 75% sulfuric acid were stirred for 3 h at 150??? C. After this dark solution was poured onto 100 g of crushed ice, 100 ml of ethylacetate (EtOAc) and 30 ml of 30% solution of NaOH. After 1 hour brown solid was filtered off and the organic layer was separated. After filtering through SiO2 and evaporation of solvent 7-bromo-5-methoxy-quinoline and 5-bromo-7-methoxy-quinoline were separated as mixture approximately 60:40 (total 3.5 g, 74%) This mixture was separated to individual 7-bromo-5-methoxy-quinoline and 5-bromo-7-methoxy-quinoline with column chromatography on silica-gel with benzene-EtOAc (3:1) as eluent. Yield of pure 7-bromo-5-methoxy-quinoline was 950 mg (27% from mixture).

According to the analysis of related databases, 16618-68-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HOFFMANN, Matthias; BISCHOFF, Daniel; DAHMANN, Georg; KLICIC, Jasna; SCHAENZLE, Gerhard; WOLLIN, Stefan Ludwig Michael; CONVERS-REIGNIER, Serge Gaston; EAST, Stephen Peter; MARLIN, Frederic Jacques; McCARTHY, Clive; SCOTT, John; US2013/29949; (2013); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem