Category: 112734-22-2

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. 112734-22-2, name is (4-Bromo-2-fluorophenyl)methanamine, A new synthetic method of this compound is introduced below., category: bromides-buliding-blocks

1000ml three-necked bottle, in the case of nitrogen 50.0 g of starting material A (211 mmol), 50.7 g of sodium t-butoxide (527 mmol), 0.97 g of Pd2(dba)3 (1.05 mmol),0.87g of S-phos (2.04mmol) and 150ml of xylene, heated to 130 C ~ 140 C, temperature control 130 C ~ 140 C slowly added 43.0g of raw material B (211mmol) and 400ml of xylene mixed solution, add dropwise, Keep warm for 15h, TLC detects the completion of the reaction; cools to room temperature, Filter and filter the cake with xylene. The column liquid was steamed to a non-fraction, and the crude yellow solid was purified with toluene. Drying to obtain 53.2 g of intermediate A, yield: 70%,

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; Yantai Jiu Mu Chemicals Co., Ltd.; Liu Kai; Song Sisi; Wang Peng; Sang Hongjian; Cai Qinggong; Tang Renmao; (23 pag.)CN109369557; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 112734-22-2, 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 112734-22-2 as follows.

A solution of 5-chloro-2-hydroxy-benzoyl chloride (4.00 g, 23.2 mmol) in dichloromethane (46 mL, 0.5 M) was treated with triethylamine (6.46 mL, 46.4 mmol) and 4-bromo-2-fluorobenzylamine (6.10 g, 30.1 mmol). After stirring at room temperature for 16 h, the solution was washed successively with 2 N HCl and saturated aq NaCl. The organic layer was dried over Na2SO4, filtered and concentrated. Purification by MPLC (10-50% ethyl acetate in heptane, 23 mL/min, 70 min) gave N-(4-bromo-2-fluoro-benzyl)-4-chloro-2-hydroxy-benzamide as a white crystalline solid (4.4 g, 53%): mp 159-161 C.; Rf 0.49 (30% ethyl acetate in heptane); 1H NMR (DMSO-d6, 300 MHz) delta 12.56 (br s, 1H), 9.28 (br t, J=5.4 Hz, 1H), 7.88 (d, J=6.0 Hz, 1H), 7.50 (dd, J1=9.9 Hz, J2=1.8 Hz, 1H), 7.37 (dd, J1=8.4 Hz, J2=1.8 Hz, 1H), 7.33 (dd, J1=15.9 Hz, J2=8.1 Hz, 1H), 6.99-6.93 (m, 2H), 4.50-4.46 (m, 2H). ESI-LC/MS m/z calcd for C14H10BrClFNO2: 358.6; found 360.0 (M+1)+. Anal. calcd for C14H10BrClFNO2: C, 46.89; H, 2.81; N, 3.91; Cl, 19.78. Found C, 46.89; H, 2.81; N, 3.90; Cl, 19.73.

According to the analysis of related databases, 112734-22-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; The Institute for Pharmaceutical Discovery LLC; US6420426; (2002); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 112734-22-2, 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. 112734-22-2, name is (4-Bromo-2-fluorophenyl)methanamine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of (4-bromo-2-fluoro-phenyl)methanamine (5.00mmol) in THF (4 mL), a propylphosphonic anhydride solution(50 wt% in EtOAc, 7.50 mmol) in THF (6 mL), 2-methoxy-5-methylbenzoic acid (6.04 mmol), and N,Ndiisopropylethylamine (8.88 mmol) was stirred at 80 C for 18 h. The reaction was cooled to RT and partitioned between EtOAc and a saturated aqueous solution of NH4CI. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified to give the titled compound (3.51 mmol). UPLC-MS (ES, Short acidic): 2.05 mi m/z 353.9 [M+2]

The synthetic route of (4-Bromo-2-fluorophenyl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; REDX PHARMA PLC; GUISOT, Nicolas; (266 pag.)WO2017/103611; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 112734-22-2, name is (4-Bromo-2-fluorophenyl)methanamine, 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 112734-22-2, Product Details of 112734-22-2

(2) To a solution of 4-bromo-2-fluorobenzylamine (0.93 g) and triethylamine (1.3 ml) in N,N-dimethylformamide (5 ml) was added a solution of ethyl (R)-2,5-dioxo-3-(2-trichloroacetylpyrrol-1-yl)pyrrolidine-3-carboxylate (1.16 g) in N,N-dimethylformamide (3 ml) dropwise at room temperature. This mixture was stirred at room temperature for 8 hours. This reaction mixture was diluted with ethyl acetate, then washed with 1M hydrochloric acid (three times), water (four times), and saturated brine successively, dried over magnesium sulfate, filtered and concentrated to give a crude product as yellow oil. This was purified by flash column chromatography (n-hexane:ethyl acetate=2:1) to give (3R)-2′-(4-bromo-2-fluorobenzyl)spiro[pyrrolidine-3,4′(1’H)-pyrrolo[1,2-a]pyrazine]-1′,2,3′,5(2H’)-tetraone (831 mg, 65%). This product was further crystallized from n-hexane-ethyl acetate to give the desired product (385 mg) as crystal.Mp: 189-191 C. 1H NMR (400 MHz, DMSO-d6, 22 C.) delta: 12.2 (br s, 1H), 7.73 (dd, 1H, J=2.0, 3.2 Hz), 7.55 (dd, 1H, J=2.0, 9.6 Hz), 7.36 (dd, 1H, J=2.0, 8.4 Hz), 7.17-7.12 (m, 2H), 6.53 (dd, 1H, J=2.8, 4.0 Hz), 5.04 (d, 1H, J=15.2 Hz), 4.96 (d, 1H, J=15.6 Hz), 3.57 (s, 2H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Tanaka, Daisuke; US2009/253917; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 112734-22-2, These common heterocyclic compound, 112734-22-2, name is (4-Bromo-2-fluorophenyl)methanamine, 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.

Step 1 : To a stirred solution of (4-bromo-2-fluorophenyl)methanamine (2.5 g, 12.25 mmol) in pyridine (10 mL) at 0 C in a protective gas atmosphere was added methanesulfonyl chloride (1 .422 mL, 18.38 mmol) slowly in portions. After addition, the suspension was stirred at 0 C for 1 h. The reaction mixture was diluted with ice cold water (20 mL) and pH was adjusted to ~1 using 16 % aqueous HCI solution. The resulting precipitation was filtered off, washed with ethyl acetate (3 x 20 mL) and dried overnight. The crude N-(4-bromo-2-fluorobenzyl)- methanesulfonamide (3.14 g, 91 %) was used as such without further purification.

The synthetic route of 112734-22-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUeNENTHAL GMBH; FRANK, Robert; BAHRENBERG, Gregor; CHRISTOPH, Thomas; LESCH, Bernhard; LEE, Jeewoo; WO2013/45451; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 112734-22-2, 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. 112734-22-2 name is (4-Bromo-2-fluorophenyl)methanamine, 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.

Example 12 Preparation of (3R)-2′-(4-bromo-2-fluorobenzyl)spiro[pyrrolidin-3,4′(1’H)-pyrrolo[1,2-a]pyrazin]-1′,2,3′,5(2’H)-tetraone 2,5-Dimethoxytetrahydrofuran (7.4 g) and 2.5% aqueous acetic acid (50 g) were added to ethyl (2R)-2-amino-2-ethoxycarbonylsuccinimide (10 g)and the mixture was stirred at 70C for 1.5 hours. The reaction solution was cooled and insoluble materials were dissolved by addition of ethyl acetate (50 ml) and stirring. The mixture was placed for a while and the organic layer was separated from the aqueous layer, washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo, diisopropylether (37 g) and ethyl acetate (9.2 g) were added to the residue and diisopropylamine (6.2 g) was added and the mixture was stirred at 0-5C of inner temperature. The precipitated crystals were filtered, washed with diisopropylether and dried to give (2R)-2-ethoxycarbonyl-2-(pyrrol-1-yl)succinimide diisopropylamine salt(yield 88%). To a suspension of (2R)-2-ethoxycarbonyl-2-(pyrrol-1-yl)succinimide diisopropylamine salt (20.0 g) in ethyl acetate (100 ml), was added 20% aqueous sulfuric acid (16 ml) and the salt was dissolved. The solution was placed after stirring and the organic layer was separated with the aqueous layer. The organic layer was separated with the aqueous layer again after brine was added to the organic solution, and the mixture was stirred and placed. The organic layer was concentrated in vacuo, ethyl acetate (50 ml) and trichloroacetyl chloride (32.3 g) were added to the residue and the mixture was stirred under reflux for 6 hours. The reaction solution was cooled, ethyl acetate (134 ml) was added thereto and it was washed with brine, aqueous solution of sodium bicarbonate, 5% aqueous sulfuric acid and brine successively. The organic layer was concentrated in vacuo, N-methyl pyrrolidone (26 ml) and ethyl acetate(6.7 ml) were added and the residue was dissolved. The solution was cooled and diisopropylamine (9 g) was added thereto and the mixture was stirred. 4-Bromo-2-fluorobenzylamine (24.2 g) was added dropwise under ice-cooling and the mixture was stirred at 0-5C for 18 hours. Ethyl acetate (266 ml) was added to the reaction solution and it was washed with 5% aqueous sulfuric acid, aqueous solution of sodium bicarbonate, 5% aqueous sulfuric acid and brine successively. The organic layer was concentrated in vacuo, ethanol (100 ml) was added to the residue and it was dissolved under heating to reflux. Ethanol (33 ml) was evaporated, the concentrated solution was cooled with ice-water and the precipitated crystals were filtered and washed with ethanol. The resulting wet crystals were recrystallized from isopropanol (124 ml and 180 ml) twice to give (3R)-2′-(4-bromo-2-fluorobenzyl)spiro[pyrrolidin-3,4′(1’H)-pyrrolo[1,2-a]pyrazin]-1′,2,3′,5(2’H)-tetraone (yield 58%).

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

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; Katayama Seiyakusyo Co. Ltd.; EP2058300; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 112734-22-2, These common heterocyclic compound, 112734-22-2, name is (4-Bromo-2-fluorophenyl)methanamine, 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.

Boc20 (106.96 mg, 490.10 muiotaetaomicron) and DMAP (5.99 mg, 49.01 muiotaetaomicron) were added to a solution of Compound BD2-2 (100.00 mg, 490.10 muiotaetaomicron) and TEA (148.78 mg, 1.47 mmol) in DCM (4.00 mL). The mixture was stirred at 15C for 12 hours. LCMS showed the reaction was completed. The mixture was concentrated to get crude residue. The residue was purified by prepatory-TLC (S1O2, Petroleum ether:Ethyl acetate mixture with a ratio of 5: 1) to afford Compound BD2-3 (90.00 mg, crude) as a yellow oil.

Statistics shows that (4-Bromo-2-fluorophenyl)methanamine is playing an increasingly important role. we look forward to future research findings about 112734-22-2.

Reference:
Patent; THE BROAD INSTITUTE, INC.; VACCA, Joseph, P.; (103 pag.)WO2018/75871; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 112734-22-2, name is (4-Bromo-2-fluorophenyl)methanamine, 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 112734-22-2, Product Details of 112734-22-2

Step 1 : 4-Bromo-2-fluorobenzylamine (924 mg, 4.53 mmol) was dissolved in pyridine and ethane sulfonyl chloride (0.82 mL, 8.60 mmol) was added to the solution at O C. The mixture was stirred for 1 h at O C. Then, the mixture was quenched with 1 N HCl and extracted with ethyl acetate (EtOAc). Drying (MgSO4) and evaporation of the ethyl acetate followed and the residue was purified by CC (eluent EtOAc/n-hexane) to yield N-(4-bromo-2- fluorobenzyl)ethanesulfonamide in pure form (1 .06 g, 79 %).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; GRUeNENTHAL GMBH; FRANK, Robert; CHRISTOPH, Thomas; DAMANN, Nils; LESCH, Bernhard; BAHRENBERG, Gregor; SAUNDERS, Derek John; STOCKHAUSEN, Hannelore; KIM, Yong-Soo; KIM, Myeong-Seop; LEE, Jeewoo; WO2013/68462; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 112734-22-2, These common heterocyclic compound, 112734-22-2, name is (4-Bromo-2-fluorophenyl)methanamine, 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.

Step c) 2-[(4-Bromo-2-fluorophenyl)methyl]-1,2,3,4-tetrahydro-1,3-dioxo-4-isoquino-linecarboxylic Acid Methyl Ester To a solution of 3-methoxy-1-oxo-1H-2-benzopyran-4-carboxylic acid methyl ester (5.0 g, 21.37 mmol) in DMF (100 mL) were added 4-bromo-2-fluorobenzylamine (4.36 g, 21.37 mmol) and Et3 N (5.96 mL, 42.74 mmol). The mixture was stirred at 80 C. for 30 minutes, poured into H2 O (1500 mL), acidified with HCl (2N) and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and crystallization from acetone/hexane (after cooling to -20 C.) gave a white solid (7.6 g, 87.7%, m.p. 149-150 C.). 1 H NMR (DMSO-d6, 400 MHz): delta [3.67 (s), 4.0 (s), 3H, –CO2 Me, tautomeric], [5.06 (q), J=15.4 Hz, 5.30 (s), 2H, –NCH2 –, tautomeric], 5.4 (s), 1H, CH–CO2 Me, tautomeric], 7.07-8.43 (m, 7H, Ar–H, tautomeric) IR (KBr, cm-1): 1670 (CO), 1605 (CO) MS (+FAB): 406 (80, M+ +H), 374 (470, M+ –OCH3) Anal. Calcd.: C, 53.22; H, 3.23; N, 3.45; Found: C, 53.19; H, 2.98; N, 3.40.

The synthetic route of 112734-22-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Home Products Corporation; US5102886; (1992); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 112734-22-2, 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 112734-22-2 as follows.

General procedure: To a stirred solution of N-(t-butoxycarbonyl)glycine (1 mmol) in CH2Cl2 (10 mL) was added CDI (1.1 mmol), and the resulting mixture was stirred at room temperature for 1 h. To the resulting mixture was added amine (1 mmol), and the reaction mixture was stirred at room temperature for 24 h. The solvent was removed under reduced pressure, and the residue was chromatographed on silica gel (20 g, hexane : acetone = 6 : 1 ~ 3 : 1) to give the corresponding amide.

According to the analysis of related databases, 112734-22-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Mori, Hisashi; Wada, Ryogo; Li, Jie; Ishimoto, Tetsuya; Mizuguchi, Mineyuki; Obita, Takayuki; Gouda, Hiroaki; Hirono, Shuichi; Toyooka, Naoki; Bioorganic and Medicinal Chemistry Letters; vol. 24; 16; (2014); p. 3732 – 3735;,
Bromide – Wikipedia,
bromide – Wiktionary