Category: 102170-53-6

These common heterocyclic compound, 102170-53-6, name is 4-Bromo-5-chloro-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. Product Details of 102170-53-6

A 500-mL round-bottom flask was charged with (E)-/er/-butyl 3-(3-methoxy-3-oxoprop-l-en-l-yl)-4-(((trifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-l(2H)-carboxylate (Preparation 3a, (10.8 g, 26.0 mmol), xantphos (1.88 g, 3.25 mmol), cesium carbonate (25.4 g, 78.0 mmol), 4-bromo-5-chloro-2-methoxyaniline (6.15 g, 26.0 mmol), tris(dibenzylideneacetone)dipalladium (0) (1.19 g, 1.30 mmol) and 1,4-dioxane (130 mL) then sparged with nitrogen for 15 min. The reaction mixture stirred vigorously for 20 h at ambient temperature. The reaction mixture was subsequently vacuum filtered through a 1.0 cm plug of silica gel and the pad was rinsed with EtOAc (3 x 150 mL). The filtrate was concentrated under reduced pressure to give a brown foam that was used immediately without further purification.[00562] The product was diluted with MeOH (260 mL) and transferred to a 350-mLpressure vessel equipped with a stir bar. The reaction vessel was subsequently charged with sodium methoxide (25 wt. % in MeOH, 2.97 ml, 13.00 mmol) and sealed with a Teflon cap equipped with a pressure-relief valve. The reaction vessel was placed in a 70 C oil bath and stirred vigorously. After 5 h, the reaction mixture was allowed to cool to ambient temperature, transferred to a 1-L round-bottom flask with additional MeOH and concentrated under reduced pressure. The brown oil was redissolved in DCM (150 mL) and filtered through a pad of Celite (3 cm) to facilitate loading the material onto a column. The Celite pad was rinsed with DCM (3 x 50 mL). The brown filtrate was concentrated under reduced pressure and purified by flash column chromatography (340-g Biotage column, eluent: gradient, 5 to 35% 3:1 EtOAc/EtOH in heptane with DCM as a 10% additive) to afford (Rac)-tert-butyl 1-(4-bromo-5-chloro-2-methoxyphenyl)-2-oxo-1,2,7,8-tetrahydro-1,6-naphthyridine-6(5H)-carboxylate (9.12 g, 19.4 mmol, 74.7 % yield) as a tan solid.

The synthetic route of 4-Bromo-5-chloro-2-methoxyaniline 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;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 102170-53-6, name is 4-Bromo-5-chloro-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. HPLC of Formula: C7H7BrClNO

A 500-mL round-bottom flask was charged with (E)-/er/-butyl 3-(3-methoxy-3-oxoprop-l-en-l-yl)-4-(((trifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-l(2H)-carboxylate (Preparation 3a, (10.8 g, 26.0 mmol), xantphos (1.88 g, 3.25 mmol), cesium carbonate (25.4 g, 78.0 mmol), 4-bromo-5-chloro-2-methoxyaniline (6.15 g, 26.0 mmol), tris(dibenzylideneacetone)dipalladium (0) (1.19 g, 1.30 mmol) and 1,4-dioxane (130 mL) then sparged with nitrogen for 15 min. The reaction mixture stirred vigorously for 20 h at ambient temperature. The reaction mixture was subsequently vacuum filtered through a 1.0 cm plug of silica gel and the pad was rinsed with EtOAc (3 x 150 mL). The filtrate was concentrated under reduced pressure to give a brown foam that was used immediately without further purification.[00562] The product was diluted with MeOH (260 mL) and transferred to a 350-mLpressure vessel equipped with a stir bar. The reaction vessel was subsequently charged with sodium methoxide (25 wt. % in MeOH, 2.97 ml, 13.00 mmol) and sealed with a Teflon cap equipped with a pressure-relief valve. The reaction vessel was placed in a 70 C oil bath and stirred vigorously. After 5 h, the reaction mixture was allowed to cool to ambient temperature, transferred to a 1-L round-bottom flask with additional MeOH and concentrated under reduced pressure. The brown oil was redissolved in DCM (150 mL) and filtered through a pad of Celite (3 cm) to facilitate loading the material onto a column. The Celite pad was rinsed with DCM (3 x 50 mL). The brown filtrate was concentrated under reduced pressure and purified by flash column chromatography (340-g Biotage column, eluent: gradient, 5 to 35% 3:1 EtOAc/EtOH in heptane with DCM as a 10% additive) to afford (Rac)-tert-butyl 1-(4-bromo-5-chloro-2-methoxyphenyl)-2-oxo-1,2,7,8-tetrahydro-1,6-naphthyridine-6(5H)-carboxylate (9.12 g, 19.4 mmol, 74.7 % yield) as a tan solid.

The synthetic route of 4-Bromo-5-chloro-2-methoxyaniline 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;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 102170-53-6, A common heterocyclic compound, 102170-53-6, name is 4-Bromo-5-chloro-2-methoxyaniline, molecular formula is C7H7BrClNO, 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.

Example 20: Preparation of N-[4-(5-chloro-2-methylbenzoxazol-6-yl)phifluorophenyl)carboxamide (57):; Preparation of 2-amino-5-bromo-4-chlorophenol (53): To a suspension of 4- bromo-3-chloro-6-methoxyaniline (52) (5g, 21.1 mmol) in 50 ml DCM was added 1 M BBr3 in DCM (43 ml, 43 mmol) at 0C. The reaction mixture was stirred at r.t. for 3h, which turned to a light brown solution and back to a light brown suspension. After quenched with aq. sodium bicarbonate solution, the mixture was extracted with EA. The org. phase was washed with brine, dried over sodium sulfate, concentrated to dryness to give 4.746g 53 as light brown solid. Yield: 100%, purity > 95%.

The synthetic route of 102170-53-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CALCIMEDICA, INC.; WHITTEN, Jeffrey P.; PEI, Yazhong; CAO, Jianguo; WANG, Zhijun; ROGERS, Evan; DYCK, Brian; GREY, Jonathan; WO2011/139765; (2011); A2;,
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. 102170-53-6, name is 4-Bromo-5-chloro-2-methoxyaniline, A new synthetic method of this compound is introduced below., Quality Control of 4-Bromo-5-chloro-2-methoxyaniline

This compound was prepared using a method analogous to that of 4-amino-2,5- dimethylbenzonitnle, 4-bromo-5-chloro-2-methoxyaniline replacing 4-bromo-2,5-dimethyl aniline except that the reaction mixture was stirred ON at 110C. LC-MS (A): tR = 0.76 min, [M+H]+: 183.19

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; ACTELION PHARMACEUTICALS LTD; HILPERT, Kurt; HUBLER, Francis; RENNEBERG, Dorte; STAMM, Simon; WO2014/97140; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 102170-53-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 102170-53-6 name is 4-Bromo-5-chloro-2-methoxyaniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Preparation of 2-amino-5-bromo-4-chlorophenol (29): To a suspension of 4-bromo-3-chloro-6-methoxyaniline (28) (944 mg, 4 mmol) in 10 ml DCM was added 1 M BBr3 in DCM (8 ml, 8 mmol). The reaction mixture was stirred at r.t. for 2 h, which turned to a brown solution and back to a brown suspension. After quenched with aq. sodium bicarbonate solution, the mixture was extracted with EA. The org. phase was washed with brine, dried over sodium sulfate, concentrated to dryness to give 865 mg of 29 as a brown solid. Yield: 97.2%, purity>95%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-5-chloro-2-methoxyaniline, and friends who are interested can also refer to it.

Reference:
Patent; CalciMedica, Inc.; US2011/263612; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 102170-53-6, name is 4-Bromo-5-chloro-2-methoxyaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 4-Bromo-5-chloro-2-methoxyaniline

Preparation of 2-(5-chloro-2-methylbenzoxazol-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4) Preparation of 2-amino-5-bromo-4-chlorophenol (2): To a suspension of 4-bromo-3-chloro-6-methoxyaniline (1) (944 mg, 4 mmol) in 10 ml DCM was added 1 M BBr3 in DCM (8 ml, 8 mmol). The reaction mixture was stirred at r.t. for 2 h, which turned to a brown solution and back to a brown suspension. After quenched with aq. sodium bicarbonate solution, the mixture was extracted with EA. The org. phase was washed with brine, dried over sodium sulfate, concentrated to dryness to give 865 mg 2 as brown solid. Yield: 97.2%, purity>95%.

The synthetic route of 102170-53-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CalciMedica, Inc.; US2012/53210; (2012); 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. 102170-53-6, name is 4-Bromo-5-chloro-2-methoxyaniline, A new synthetic method of this compound is introduced below., SDS of cas: 102170-53-6

Intermediate 7: 2-Amino-5-bromo-4-chlorophenol 4-Bromo-5-chloro-2-methoxyaniline (Intermediate 6, 10g, 42.3 mmol) in DCM (200 mL) was cooled to 0 C. Boron tribromide (21 .2 g, 84.6 mmol) was added drop-wise over 30 min, the reaction mixture was stirred at 0 C for 1 h and then at room temperature for 14 h. The reaction mixture was poured into ice water, sodium hydrogen carbonate was added until pH >7 and aqueous layer was extracted with ethyl acetate (300 mL x 3). The organic phase was dried over magnesium sulphate and the solvent removed under vacuum to give 2-amino-5-bromo-4-chlorophenol as a red solid (8.4 g, 89%, used without further purification for the next step). LCMS (A): Rt 1.46 min, MH+ 222/224.

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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; BOUILLOT, Anne Marie Jeanne; MIRGUET, Olivier; LIDDLE, John; WALKER, Ann, Louise; WO2015/91647; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

102170-53-6, name is 4-Bromo-5-chloro-2-methoxyaniline, 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. category: chlorides-buliding-blocks

To each of 2 ice/water cooled flasks, containing 4-bromo-5-chloro-2-methoxyaniline (120 g, 507.42 mmol) in DCM (1000 mL) was added boron tribromide (382 g, 1522.26 mmol). After addition, the mixture was warmed to room temperature and stirred for 2 h. The reactionmixtures were poured into ice/water (2L), basified with solid sodium bicarbonate to pH 7 and extracted with ethyl acetate (l000mL x 6). The combined organics were dried over sodium sulphate and the solvent removed to give 2-amino-5-bromo-4-chlorophenol as a brown solid (220 g).LCMS: Rt 1.35 mi MH 222/224.

The synthetic route of 102170-53-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; BOUILLOT, Anne Marie Jeanne; DENIS, Alexis; LIDDLE, John; MIRGUET, Olivier; WALKER, Ann, Louise; (64 pag.)WO2016/188827; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics