Category: 6358-77-6

Synthetic Route of 6358-77-6, A common heterocyclic compound, 6358-77-6, name is 5-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.

General procedure: Preparation of (±)-12: A pressure glass tube charged with trifluoroborate (±)-10 (31 mg, 0.10 mmol), Cs2CO3 (98 mg, 0.30 mmol) and PdCl2(dppf)·CH2Cl2 (4 mg, 5 mol %) was alternatively evacuated and sparged with argon three times. A solution of 4-bromoanisol (21 mg, 0.11 mol) in toluene (1.5 mL) previously flushed with argon, then water (0.5 mL) were added by syringes. The reaction mixture was stirred at 100 C for 18 h and then cooled to room temperature. Water (5 mL) was added and the mixture extracted with EtOAc (5 mL × 2). The combined organic layers were washed with water (5 mL × 2), dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography (cyclohexane/EtOAc 9:1), affording 12 as a colorless oil (24 mg, 75%).

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; Ty, Nancy; Pontikis, Renee; Chabot, Guy G.; Devillers, Emmanuelle; Quentin, Lionel; Bourg, Stephane; Florent, Jean-Claude; Bioorganic and Medicinal Chemistry; vol. 21; 5; (2013); p. 1357 – 1366;,
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Reference of 6358-77-6, These common heterocyclic compound, 6358-77-6, name is 5-Bromo-2-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.

A solution of sodium bicarbonate (3.74 g, 44.5 mmol) in water (75 mL) was added to commercially available 5-bromo-2-methoxy-phenylamine (3 g, 14.8 mmol) in chloroform (75 mL). Thiophosgene (1.42 mL, 18.6 mmol) was then added. The biphasic solution was stirred at room temperature for 1 h. The phases were separated and the aqueous phase was extracted with CH2Cl2. The organic phase was dried (Na2SO4), filtered, and concentrated, yielding the crude title compound as an off-white solid.

The synthetic route of 6358-77-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WANG, Aihua; Zhang, Yan; Leonard, Kristi Anne; Hawkins, Michael; Tounge, Brett Andrew; Maharoof, Umar S.M.; Barbay, Joseph Kent; US2012/129811; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 6358-77-6, name is 5-Bromo-2-methoxyaniline, A new synthetic method of this compound is introduced below., SDS of cas: 6358-77-6

A 50-mL round-bottom flask was charged with 5-bromo-2-methoxy aniline(Alfa Aesar, 1.00 g, 4.95 mmol), 3-chloro-4-methylphenylboronic acid (Acros, 1.69 g, 9.90 mmol), 1,1 ‘-bis(diphenylphosphino)ferrocene palladium(II)dichloride dichloromethane adduct (0.81 g, 0.99 mmol), and purged with nitrogen. 1,4-Dioxane (37.1 ml) and an aqueous sodium carbonate solution (1.9 M, 12.4 mL) were introduced and the reaction mixture was warmed to 80 C. After 90 min, the reaction mixture was allowed to cool to ambient temperature and diluted with aqueous HCI solution (1.0 M, 25 mL) and EtOAc (25 mL). The layers were separated and the aqueous layer extracted with additional EtOAc (2 x 25 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure and purified by flash column chromatography (100-g silica gel Biotage column, eluent: gradient, 0 to 40% EtOAc in heptane with DCM as a 5% additive) to afford 3′-chloro-4-methoxy-4′-methyl-[l,l’-bipheny 1]-3-amine (1.03 g, 4.16 mmol, 84.0 % yield) as a tan solid.

The synthetic route of 6358-77-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; USA Anjin Corporation; M .weisi; B .C.miergelamu; T .dining; J .siteerwogen; A .gusiman-peileisi; A .beiqiao; I .E.makesi; (177 pag.)CN107531705; (2018); A;,
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Synthetic Route of 6358-77-6, A common heterocyclic compound, 6358-77-6, name is 5-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.

Intermediate 14: step a 4-Bromo-2-isothiocyanato-1-methoxy-benzene A solution of sodium bicarbonate (3.74 g, 44.5 mmol) in water (75 mL) was added to commercially available 5-bromo-2-methoxy-phenylamine (3 g, 14.8 mmol) in chloroform (75 mL). Thiophosgene (1.42 mL, 18.6 mmol) was then added. The biphasic solution was stirred at room temperature for 1 h. The phases were separated and the aqueous phase was extracted with CH2Cl2. The organic phase was dried (Na2SO4), filtered, and concentrated, yielding the crude title compound as an off-white solid.

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; JACKSON, Paul Francis; Manthey, Carl; Rhodes, Kenneth; Scannevin, Robert; Leonard, Kristi Anne; Barbay, Joseph Kent; Todd, Matthew; Springer, Barry A.; US2012/302573; (2012); A1;,
Ether – Wikipedia,
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Synthetic Route of 6358-77-6, A common heterocyclic compound, 6358-77-6, name is 5-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.

b. 4-(5-Bromo-2-methoxyanilino)-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine The title compound was prepared from a mixture of 4-chloro-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine (50 mg, 0.193 mmol) and 5-bromo-2-methoxyaniline (39 mg, 0.193 mmol) similar to Example 117 and isolated as a tan solid (26 mg, 32%). 1H NMR (CDCl3): 9.67-9.66 (m, 1H), 8.77-8.71 (m, 3H), 7.55 (s, 1H), 7.48-7.43 (m, 1H), 7.24 (dd, J=2.4, 8.7 Hz, 1H), 6.92 (s, 1H), 6.83 (d, J=9.0 Hz, 1H), 3.93 (s, 3H).

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; Cytovia, Inc.; US2003/69239; (2003); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 6358-77-6, name is 5-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. Recommanded Product: 6358-77-6

A 50-mL round-bottom flask was charged with 5-bromo-2-methoxy aniline(Alfa Aesar, 259 mg, 1.28 mmol), (3-chloro-2-methylphenyl)boronic acid (Combi-Blocks Inc., 240 mg, 1.41 mmol), 1,l’-bis(diphenylphosphino)ferrocene palladium(II)dichloride dichloromethane adduct (209 mg, 0.26 mmol), and purged with nitrogen. 1,4-Dioxane (9.60 ml) and an aqueous sodium carbonate solution (1.9 M, 3.20 mL) were introduced and the reaction mixture was warmed to 80 C. After 90 min, the reaction mixture was allowed to cool to ambient temperature and diluted with aqueous HCI solution (1.0 M, 25 mL) and EtOAc (25 mL). The layers were separated and the aqueous layer extracted with additional EtOAc (2 x 25 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure and purified by flash column chromatography (100-g silica gel Biotage column, eluent: gradient, 0 to 40% EtOAc in heptane with DCM as a 5% additive) to afford 3′-chloro-4-methoxy-2′-methyl-[1,1′-biphenyl]-3-amine (226 mg, 0.91 mmol, 71.3 % yield) as a tan solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6358-77-6, its application will become more common.

Reference:
Patent; USA Anjin Corporation; M .weisi; B .C.miergelamu; T .dining; J .siteerwogen; A .gusiman-peileisi; A .beiqiao; I .E.makesi; (177 pag.)CN107531705; (2018); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 6358-77-6, A common heterocyclic compound, 6358-77-6, name is 5-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.

Roundbottom flask is charged with 5-bromo-2-methylaniline ( 100.00 mg; 0.54 mmol; 1 .0 eq), methanol (1.5 mL), 37 % formaldehyde solution in methanol (289.18 mg; 3.56 mmol; 2.40 eqf.) and acetic acid (104.68 mg; 1.29 mmol; 2.40 eq.). RM is stirred at room temperature for 10 minutes. After this time RM is cooled down to 0C and sodiumcyanoborohydride (70.93 mg; 1 .13 mmol; 2.10 eqf.) is added. Reaction mixture is stirred in this temperature for 1 h. Then the solvent is evaporated and reaction is quenched with saturated aqueous solution of NaHC03 (5 mL) and extracted with DCM ( 3×5 mL). Combined organic extracts are washed with water (2×10 mL). Organic solvent is then evaporated and crude product is further purified by FCC(DCM/EtOAc, gradient) to 5-bromo-N,N,2-trimethylaniline (74.20 mg; yield 61.6 %; 95.5 % by UPLC) as a colorless oil.

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; SELVITA S.A.; FABRITIUS, Charles-Henry Robert Yves; NOWAK, Mateusz Oktawian; WIKLIK, Katarzyna Anna; SABINIARZ, Aleksandra Barbara; BIE?, Marcin Dominik; BUDA, Anna Ma?gorzata; GUZIK, Pawel Szczepan; JAKUBIEC, Krzysztof Roman; MACIUSZEK, Monika; KWIECI?SKA, Katarzyna; TOMCZYK, Mateusz Micha?; GA??ZOWSKI, Micha? Miko?aj; GONDELA, Andrzej; DUDEK, ?ukasz Piotr; (681 pag.)WO2016/180536; (2016); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 6358-77-6, name is 5-Bromo-2-methoxyaniline, A new synthetic method of this compound is introduced below., Formula: C7H8BrNO

Roundbottom flask is charged with 5-bromo-2-methylaniline( 400.00 mg; 2.15 mmol; 1 .0 eg.), triethylamine ( 330.76 mL; 2.36 mmol; 1.1 eq.) and anhydrous dichloromethane (12 mL). Acetyl chloride ( 185.64 mg; 2.36 mmol; 1.1 eq.) is then added dropwise and reaction mixture is stirred at room temperature for 24h. After this time diethyl ether (24 mL) is added and mixture is washed with saturated aqueous solution of ammonium chloride (2×20 mL) and brine (2×20 mL). Organic layer is then dried over anhydrous Na2SO4 overnight. The second organic solvent is evaporated to afford N-(5- bromo-2-methylphenyl)acetamide (513.20 mg; yield 93.5 %; 89.3 % by UPLC) as brown solid.

The synthetic route of 6358-77-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SELVITA S.A.; FABRITIUS, Charles-Henry Robert Yves; NOWAK, Mateusz Oktawian; WIKLIK, Katarzyna Anna; SABINIARZ, Aleksandra Barbara; BIE?, Marcin Dominik; BUDA, Anna Ma?gorzata; GUZIK, Pawel Szczepan; JAKUBIEC, Krzysztof Roman; MACIUSZEK, Monika; KWIECI?SKA, Katarzyna; TOMCZYK, Mateusz Micha?; GA??ZOWSKI, Micha? Miko?aj; GONDELA, Andrzej; DUDEK, ?ukasz Piotr; (681 pag.)WO2016/180536; (2016); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 6358-77-6, name is 5-Bromo-2-methoxyaniline, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H8BrNO

5-(Dimethylphosphoryl)-2-methoxyaniline (0456) To a solution of 5-bromo-2-methoxyaniline (0.404 g, 2.00 mmol) in 8 mL DMF was added dimethylphosphine oxide (0.171 g, 2.20 mmol), palladium acetate (22.4 mg, 0.0100 mmol), XANTPHOS (69.4 mg, 0.120 mmol), and potassium phosphate (0.467 g, 2.20 mmol). The mixture was purged with nitrogen, and subjected to microwaves at 150 C. for 20 minutes. The reaction mixture was concentrated and purified by silica gel chromatography (0-20% 7N ammonia in methanol:dichloromethane) to afford the desired product (0.365 g, 85% yield).

The synthetic route of 6358-77-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARIAD PHARMACEUTICALS, INC.; Wang, Yihan; Huang, Wei-Sheng; Liu, Shuangying; Shakespeare, William C.; Thomas, Ranny M.; Qi, Jiwei; Li, Feng; Zhu, Xiaotian; Kohlmann, Anna; Dalgarno, David C.; Romero, Jan Antoinette C.; Zou, Dong; US2015/225436; (2015); A1;,
Ether – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 6358-77-6, name is 5-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 6358-77-6, name: 5-Bromo-2-methoxyaniline

N, N-DIISOPROPYLETHYLAMINE (13.49 ml, 77.4 mmol) and methyl bromoacetate (0.95 eq, 49.0 mmol) were added to a solution of 5-bromo-2-methoxyaniline (1 eq, 51.6 mmol) in anhydrous DMF (100 ml) under nitrogen. The solution was heated for 16 hours at 60 C before cooling to ambient temperature. DMF was removed under reduced pressure. The residue was dissolved in 500 ml of DCM, washed with 2 x 200 ml of water, was dried over sodium sulfate and was filtered and concentrated under reduced pressure. The title compound was precipitated from DCM/hexanes as an off-white, brownish solid (10.34 G)

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Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/41799; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem