Tag: M.W=200-300

Reference of 3401-47-6, A common heterocyclic compound, 3401-47-6, name is 1-Bromo-2-methoxynaphthalene, molecular formula is C11H9BrO, 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] Synthesis of 1-(2-Fluorophenyl)-2-methoxynaphthalene Into a 500 mL three-neck flask were placed 8.7 g (35 mmol) of 1-bromo-2-methoxynaphthalene, and 5.0 g (35 mmol) of 2-fluorophenylboronic acid. The air in the flask was replaced with nitrogen. To this mixture were added 120 mL of toluene, 60 mL of ethanol, and 40 mL of an aqueous solution of sodium carbonate (2.0 mol/L). While the pressure was reduced, this mixture was stirred to be degassed. To this mixture was added 2.0 g (1.7 mmol) of tetrakis(triphenylphosphine)palladium(0), and the mixture was stirred at 80 C. for 8 hours under a nitrogen stream. The aqueous layer of the obtained mixture was subjected to extraction with toluene, and the obtained solution of the extract and the organic layer were combined and washed with saturated brine. The organic layer was dried with magnesium sulfate, and this mixture was gravity-filtered. An oily substance obtained by concentration of the obtained filtrate was dissolved in about 30 mL of toluene. This solution was suction-filtered through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), alumina, and Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135). An oily substance obtained by concentration of the obtained filtrate was dried under reduced pressure, so that 5.3 g of a pale yellow oily substance of the object of the synthesis was obtained in 60% yield. The reaction scheme of Step 1 is illustrated in (E2-1).

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; Semiconductor Energy Laboratory Co., Ltd.; US2012/165550; (2012); A1;,
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Synthetic Route of 1462-37-9,Some common heterocyclic compound, 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, molecular formula is C9H11BrO, 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 83-Amino-6-(2-benzyloxy-ethoxy)-indazole-1-carboxylic acid tert-butyl esterScheme 1, Step Hb)A mixture of 3-amino-6-hydroxy-indazole-1-carboxylic acid tert-butyl ester (249 mg, 1 mmol), K2CO3 (152 mg, 1.1 mmol) and benzyl 2-bromoethyl ether (0.179 ml, 1.1 mmol) in dry DMF (5 ml) was stirred at 50°C for 12h. More benzyl 2-bromoethyl ether (30 muIota) was added and the mixture stirred at 50°C for additional 4h. The reaction mixture was poured into water (50 ml) and extracted with EtOAc (50 ml). The organic layer wad dried over sodium sulfate and evaporated to dryness. The crude residue was purified by flash chromatography over silica gel eluting with DCM / EtOAc 7:3 affording 274 mg (yield: 72percent) of the title compound.1H-NMR (400 MHz), delta (ppm, DMSO-cie): 7.71 (d, J=8.66 Hz, 1 H), 7.48 (bs, 1 H), 7.38 – 7.27 (m, 5H), 6.91 (dd, J=2.19, 8.66 Hz, 1 H), 6.19 (bs, 2H), 4.59 (s, 2H), 4.25 – 4.20 (m, 2H), 3.85 – 3.80 (m, 2H), 1.58 (s, 9H) ESI (+) MS m/z 384 (MH+)

The synthetic route of 1462-37-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.R.L.; LOMBARDI BORGIA, Andrea; CIOMEI, Marina; DONATI, Daniele; NESI, Marcella; WO2012/152763; (2012); A1;,
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1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, 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 1462-37-9

Step-1: 1-(2-(benzyloxy)ethyl)-4-iodo-lH-pyrazoleTo a stirred solution 4-iodo-lH-pyrazole (2.0 g, 10.3 mmol) in DMF (20 ml) was addedpotassium carbonate (3.5 g, 25 mmol) followed by drop wise addition of ((2-bromoethoxy)methyl)benzene (2.43 g, 11 mmol) and stirred the reaction at RT for 15 h. Thereaction was monitored by TLC (50percent ethyl acetate in hexane). The reaction mixture was dilutedwith ice water (150 ml) and extracted with ethyl acetate (2×50 ml). The organic layer was driedover Na2S04, and concentrated under reduced pressure to afford 3.1 g (91.7percent yield) of 1-(2-fluorobenzyl )-4-iodo-1 H-pyrazole.1H NMR (DMSO-d6, 300MHz): 8 7.29 (s, lH), 7.55 (s, lH), 7.37-7.22 (m, SH), 4.45 (s, 2H),4.34-4.30 (t, 2H), 3.77-3.74 (t, 2H); LCMS: rn/z = 329.1 (M+l).

The synthetic route of 1462-37-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; UM PHARMAUJI SDN. BHD; GUMMADI, Venkateshwar Rao; HOSAHALLI, Subramanya; NANDURI, Srinivas; AGGUNDA RENUKAPPA, Girish; WO2014/24077; (2014); A1;,
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Synthetic Route of 59557-91-4, The chemical industry reduces the impact on the environment during synthesis 59557-91-4, name is 4-Bromo-2-methoxyaniline, I believe this compound will play a more active role in future production and life.

4-(Dipropylphosphoryl)-2-methoxyaniline To a solution of 4-bromo-2-methoxyaniline (0.100 g, 0.495 mmol) in 2 mL DMF was added dipropylphosphine oxide (0.0730 g, 0.544 mmol), palladium acetate (5.6 mg, 0.025 mmol), XANTPHOS (17.2 mg, 0.030 mmol), and potassium phosphate (0.116 g, 0.544 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 (0-12% 7N ammonia in methanol:dichloromethane) and the fractions were concentrated. The residue was acidified with 2.5 M HCl in ethanol and the solution was concentrated to provide 4-(dipropylphosphoryl)-2-methoxyaniline as the hydrochloride salt (0.132 g, 91% yield).

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

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;,
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Electric Literature of 157869-15-3,Some common heterocyclic compound, 157869-15-3, name is 2-((4-Methoxyphenyl)ethynyl)aniline, molecular formula is C15H13NO, 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: A sealed tube was charged with the mixture of 2-alkynylaniline 1 (1 mmol), carbon disulfide (1.5 mmol), then stirred in a solution of DBUH+ in CH3CN (1.5 mL) at room temperature under nitrogen atmosphere for indicated time. After completion, then H2O (5 mL) was added and the mixture was extracted with EtOAc (5 mL x 3), dried by anhydrous Na2SO4. Evaporation of the solvent followed by purification on silica gel (petroleum ether/ethylacetate = 4/1) provided the corresponding product 2.

The synthetic route of 157869-15-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhao, Peng; Liao, Qian; Gao, Hongxin; Xi, Chanjuan; Tetrahedron Letters; vol. 54; 19; (2013); p. 2357 – 2361;,
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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. 886762-08-9, name is 5-Bromo-2-(trifluoromethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H5BrF3NO

General procedure: Compound (6) (0.38 g, 0.7 mmol), 1-[[(3,5-dimethyl phenyl)amino]carbonyl] (0.34 g, 0.92 mmol) was dissolved in anhydrousCH2Cl2 (10 mL), and HATU (0.63 g,1.66 mmol) was added, themixture was stirred on the ice-bath for 30 min, then 0.13 mLanhydrous triethylamine in anhydrous CH2Cl2 was slowly addeddropwise to the above mixture, after that, the ice bath wasremoved, and the mixturewas reacted at room temperature for 8 h.The product was extracted with CH2Cl2 (30 mL 3), washed withwater and brine (100 mL 3), and dried over Na2SO4. After filtrationand concentration in vacuo, the residues was purified by silicagel flash chromatogrphy gave (10k) (0.12 g, 25%).

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 886762-08-9.

Reference:
Article; Zhang, Lin; Shan, Yuanyuan; Li, Chuansheng; Sun, Ying; Su, Ping; Wang, Jinfeng; Li, Lisha; Pan, Xiaoyan; Zhang, Jie; European Journal of Medicinal Chemistry; vol. 127; (2017); p. 275 – 285;,
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These common heterocyclic compound, 36942-56-0, name is 2-Bromo-4-methoxy-1-methylbenzene, 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 36942-56-0

To a suspension of aluminum chloride (5.33 g)in dichloromethane (50 mL) was added a solution of 3-bromo-4-methylanisole (5.36 g)in dichloromethane (10 mL)under ice-cooling,and the mixture was stirred for 5 min. To the reaction mixture was added isobutyryl chloride,and the mixture was stirred under ice-cooling for 45 min. To the reaction mixture was added ice water,6N hydrochloric acid was added and the mixture was extracted with chloroform. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution,dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was purified by column chromatography (hexane:ethyl acetate)to give 1-(4-bromo-2-methoxy-5-methylphenyl)-2-methylpropan-1-one (4.86 g).

The synthetic route of 2-Bromo-4-methoxy-1-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; ISHIBUCHI, Seigo; SARUTA, Kunio; HAMADA, Maiko; MATOBA, Nobuatsu; MATSUDAIRA, Tetsuji; SEKI, Maki; TARAO, Akiko; HONJO, Takashi; OGATA, Shingo; KAWATA, Atsushi; MOROKUMA, Kenji; FUJIE, Naoto; AOYAMA, Yukio; (251 pag.)EP3321256; (2018); A1;,
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Synthetic Route of 24988-36-1, 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. 24988-36-1, name is 1,5-Dibromo-2,4-dimethoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Add to the dry three-necked flask with a magnetic rotor 1,3-dibromo-4,6-dimethoxybenzene (2.5000 g, 8.53 mmol, 1.0 eq.),4-tert-butylbenzeneboronic acid (3.1890 g, 17.92 mmol, 2.1 eq.),tetrakistriphenylphosphine palladium (0.9820 g, 0.85 mmol, 0.1 equivalent) and potassium carbonate (4.7160 g, 34.1 mmol, 4.0 eq.).Nitrogen gas was purged three times, then 1,4-dioxane (30 mL) and water (10 mL) were added under nitrogen.The three vials were then placed in a 110 C oil bath.After stirring for 48 hours, the reaction was monitored by thin layer chromatography. After cooling to room temperature, the organic phase was separated and aqueous was extracted with ethyl acetate (30mL×2). All the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and concentrated, and then the crude product was purified by silica gel column chromatography (eluent: petroleum ether / ethyl acetate = 20/1-10/1) to obtain A3 , white solid 3.4040 g, yield 99%.

The synthetic route of 1,5-Dibromo-2,4-dimethoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang University of Technology; Li Guijie; Dai Jianxin; Chen Shaohai; Feng Qi; (28 pag.)CN110183476; (2019); A;,
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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. 332-48-9, name is 1-(2-Bromoethoxy)-4-fluorobenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 1-(2-Bromoethoxy)-4-fluorobenzene

Dissolve methyl 4-((15)-l-(((2R)-pyrrolidin-2-carbonyl)amino)ethyl)benzoate hydrochloride (1.00 g, 3.2 mmol) in DMF (8.0 mL) at room temperature, then add K2CO3 (1.33 g, 9.6 mmol) and l-(2-bromoethoxy)-4-fluorobenzene (715 mg, 3.2 mmol), then heat the mixture to 100 C with stirring overnight. Dilute the mixture with EtOAc (100 mL), and wash with a saturated aqueous solution of NaCl (2 chi 75 mL). Discard the aqueous layers, and dry the organic layer over MgS04, filter, and concentrate under reduced pressure to a volume of ca. 10 mL. Add hexanes (100 mL, then collect the resulting precipitate by filtration and rinse with hexanes (25 mL) and air-dry to furnish the title compound as a white solid (750 mg, 57% yield). Mass spectrum (m/z): 415 (M + H)+.

The synthetic route of 332-48-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; FISHER, Matthew Joseph; KUKLISH, Steven Lee; MANNINEN, Peter Rudolph; SCHIFFLER, Matthew Allen; WARSHAWSKY, Alan M; YORK, Jeremy Schulenburg; WO2015/94902; (2015); A1;,
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Reference of 54314-84-0, These common heterocyclic compound, 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, 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.

Benzyl-3-bromopropyl ether(175 mL, 1.00 mmol) was dissolved in dimethylformamide(1 mL).N- (benzyloxycarbonyl) acetamide potassium salt(256 mg, 1.10 mmol), and the mixture was stirred at room temperature for 23 hours.The reaction was terminated by adding saturated aqueous ammonium chloride solution (about 3 mL)The reaction mixture was extracted with ethyl acetate.After washing the organic layer with water and saturated brine,And dried over anhydrous magnesium sulfate.Flash silica gel chromatography(10percent ethyl acetate / n-hexane)A colorless oil of N- (3- (benzyloxy) propyl) -N- (benzyloxycarbonyl) acetamide (311 mg, 91percent) was obtained.

Statistics shows that ((3-Bromopropoxy)methyl)benzene is playing an increasingly important role. we look forward to future research findings about 54314-84-0.

Reference:
Patent; School corporation Meijo University; Mori, Yuji; Sakai, Takeo; Fukuda, Ayumi; Kasai, Satomi; (28 pag.)JP2018/95576; (2018); A;,
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