Tag: M.W=200-300

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. 25245-34-5, name is 2-Bromo-1,4-dimethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Safety of 2-Bromo-1,4-dimethoxybenzene

EXAMPLE 214 [1,2-Dihydro-9-methoxy-2,2,4-trimethyl-5-coumarino3,4-f]quinoline (Compound 314, structure 41 of Scheme XI, where R1 =H, R2 =methoxy) 2,5-Dimethoxyphenylboronic acid (structure 37 of Scheme XI, where R1 =H, R2 =methoxy) This compound was prepared in a manner similar to that of 5-fluoro-2-methoxyphenylboronic acid (EXAMPLE 107) from 1-bromo-2,5-dimethoxybenzene (2.00 mL, 13.3 mmol), n-BuLi (2.5M in hexanes; 5.34 mL, 13.3 mmol), and trimethylborate (4.5 mL, 40 mmol) to afford 2.43 g (99%) of 2,5-dimethoxyphenylboronic acid which was used without further purification.

According to the analysis of related databases, 25245-34-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5693647; (1997); A;,
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Synthetic Route of 54314-84-0,Some common heterocyclic compound, 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, molecular formula is C10H13BrO, 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.

26.1.N-[3-(benzyloxy)propyl]-6-chloro-N-cyclopentylpyridine-3-sulfonamideA mixture of 1 g (3.84 mmol) of 6-chloro-N-cyclopentylpyridine-3-sulfonamide, 1.32 g (9.59 mmol) of K2CO3 and 0.88 mL (4.99 mmol) of [(3-bromopropoxy)methyl]benzene in 8 mL of anhydrous DMF is heated for 12 hours at 40° C.After cooling to room temperature, the medium is taken up in 300 mL of EtOAc, washed successively with water (2*100 mL), saturated NaHCO3 solution (100 mL) and brine (100 mL), dried over Na2SO4 and then concentrated under reduced pressure and purified by chromatography on a column of silica gel, eluting with a cyclohexane/EtOAc gradient of 0 to 10percent EtOAc.1.65 g of N-[3-(benzyloxy)propyl]-6-chloro-N-cyclopentylpyridine-3-sulfonamide are thus obtained in the form of an oil.Yield=99percent.1H NMR, CDCl3, 400 MHz, delta (ppm): 8.85 (s, 1H); 8.1 (d, 1H); 7.5 (d, 1H); 7.4-7.3 (m, 5H); 4.5 (s, 2H); 4.2 (m, 1H); 3.6 (t, 2H); 3.2 (dd, 2H); 2.1 (m, 2H); 1.6-1.3 (m, 8H)

The synthetic route of 54314-84-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI; US2011/294788; (2011); A1;,
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Application of 36449-75-9, 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. 36449-75-9, name is 1-(2-Bromoethyl)-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

Example 76 3-(1-((3,5-Dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)-1-(2-methoxyphenethyl)imidazolidine-2,4-dione Prepared as in example 52 from 3-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)imidazolidine-2,4-dione (example 1) and 2-methoxyphenethyl bromide. Yield: 52%. 1H NMR (DMSO-d6, 400 MHz): delta2.11 (s, 3H), 2.38 (s, 3H), 2.80 (t, J=7.2 Hz, 2H), 3.51 (t, J=7.2 Hz, 2H), 3.75 (s, 3H), 4.03 (s, 2H), 5.17 (s, 2H), 6.85 (t, J=7.2 Hz, 1H), 6.95 (d, J=8.4 Hz, 1H), 7.16-7.21 (m, 2H), 7.73 (s, 1H), 8.13 (s, 1H). MS M+H calculated 410.2. found 410.1. Melting point: 97-98 C. The title compound was shown to inhibit hT2R08 bitter receptor and had an IC50 of 0.14 muM. Example 52 3-(1-((3,5-Dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)-1,5,5-trimethylimidazolidine-2,4-dione 3-(1-((3,5-Dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)-5-methylimidazolidine-2,4-dione (example 41) (50 mg, 0.173 mmol) and 60% NaH (8 mg, 0.190 mmol) were mixed in DMF (1 mL) for 30 minutes. MeI (0.04 mL, 0.190 mmol) was added and the reaction was stirred an additional 4 hours. The reaction was acidified with 1N HCl and diluted with ethyl acetate (2 mL). The organic phase was dried, filtered and solvent was removed under a stream of nitrogen. The crude product was re-suspended in MeOH (1 mL) and purified by reversed phase HPLC (5 to 95% acetonitrile in H2O: 16 minutes gradient). The pure fractions were combined and solvent removed under vacuum to afford 3-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)-1,5,5-trimethylimidazolidine-2,4-dione as a white solid (25 mg, 50%). 1H NMR (CDCl3, (CDCl3, 400 MHz): delta 1.45 (s, 6H), 2.19 (s, 3H), 2.42 (s, 3H), 2.94 (s, 3H), 5.05 (s, 2H), 7.92 (s, 1H), 8.08 (s, 1H). The title compound was shown to inhibit hT2R08 bitter receptor and had an IC50 of 0.80 muM.

The chemical industry reduces the impact on the environment during synthesis 1-(2-Bromoethyl)-2-methoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SENOMYX, INC.; PATRON, Andrew; TACHDJIAN, Catherine; SERVANT, Guy; DITSCHUN, Tanya; (257 pag.)US2016/376263; (2016); A1;,
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Electric Literature of 175278-17-8,Some common heterocyclic compound, 175278-17-8, name is 2-Bromo-4-(trifluoromethoxy)aniline, molecular formula is C7H5BrF3NO, 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 mixture of 2-bromo-4-(trifluoromethoxy)aniline 17 (Maybridge, 2.048 g, 8.00 mmol), methyl acrylate (1.80 mL, 20.0 mmol), Pd(OAc)2 (215.5 mg, 0.960 mmol), tri-o-tolylphosphine (1.169 g, 3.84 mmol), and dry Et3N (4.30 mL, 30.9 mmol) in dry CH3CN (16.0 mL) was stirred under reflux conditions under N2 for 4 h, then concentrated in vacuo. The residue was partitioned between H2O (30 mL) and AcOEt (30 mL). The organic layer was separated and the aqueous layer was extracted with AcOEt (30 mL × 2). The organic layers were combined, dried over anhydrous MgSO4, filtered, and concentrated in vacuo to afford 3.630 g of the title product 21 (crude). This compound was used for the next step without further purification. 1H NMR (270 MHz, CDCl3) delta 7.74 (1H, d, J = 15.8 Hz), 7.23-7.02 (2H, m), 6.68 (1H, d, J = 8.72 Hz), 6.36 (1H, d, J = 15.8 Hz), 4.00 (2H, br s), 3.81 (3H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-4-(trifluoromethoxy)aniline, its application will become more common.

Reference:
Article; Hayashi, Shigeo; Ueno, Naomi; Murase, Akio; Nakagawa, Yoko; Takada, Junji; European Journal of Medicinal Chemistry; vol. 50; (2012); p. 179 – 195;,
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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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

To a mixture of 1-(2-hydroxyethyl)-4-[2-(4-hydroxyphenyl)ethyl]-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyloxy)-1H-indazole (2 g), cesium carbonate (1.64 g) and sodium iodide (0.38g) in N,N-dimethylformamide (10 mL) was added benzyl 3-bromopropyl ether (0.86 g), and the mixture was stirred at room temperature overnight. The reaction mixture was poured into water, and the resulting mixture was extracted with diethyl ether. The extract was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was dissolved in dichloromethane (15 mL). To the solution were added triethylamine (1.22 mL) and pivaloyl chloride (0.93 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was poured into 0.5 mol/L hydrochloric acid, and the resulting mixture was extracted with diethyl ether. The extract was washed with water, a saturated aqueous sodium hydrogen carbonate solution and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate = 3/1) to give 4-{2-[4-(3-benzyloxypropoxy)phenyl]ethyl}-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyloxy)-1-(2-pivaloyloxyethyl)-1H-indazole (2.11 g). This material was dissolved in ethyl acetate (20 mL). To the solution was added 10percent palladium-carbon powder (0.5 g), and the mixture was stirred at room temperature under a hydrogen atmosphere for 2 hours. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate = 2/1 – 1/1) to give the title compound (1.59 g). 1H-NMR (CDCl3) delta ppm: 1.02 (9H, s), 1.03 (9H, s), 1.13 (9H, s), 1.15 (9H, s), 1.17 (9H, s), 2.0-2.1 (2H, m), 2.8-2.9 (1H, m), 2.9-3.0 (1H, m), 3.0-3.15 (1H, m), 3.2-3.3 (1H, m), 3.8-3.9 (2H, m), 3.9-4.0 (1H, m), 4.05-4.2 (3H, m), 4.21 (1H, dd, J=12.4Hz, 1.6Hz), 4. 3-4. 5 (4H, m), 5.2-5.3 (1H, m), 5.35-5.55 (2H, m), 6.05 (1H, d, J=7.8Hz), 6.64 (1H, d, J=6.9Hz), 6.75-6.85 (2H, m), 7.0-7.1 (3H, m), 7.15-7.2 (1H, m)

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; Kissei Pharmaceutical Co., Ltd.; EP1724278; (2006); A1;,
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Synthetic Route of 5111-65-9, These common heterocyclic compound, 5111-65-9, name is 2-Bromo-6-methoxynaphthalene, 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.

Reference Example 22 Preparation of 2-formyl-6-methoxynaphthalene n-BuLi in hexane (1.59M, 125 ml) was added dropwise to a solution of 2-bromo-6-methoxynaphthalene (42.27 g) in THF (600 ml) at -78 C. and was stirred at -78+ C. for 30 minutes. To the mixture was added DMF (28 ml), and the whole was allowed to warm to room temperature. The reaction mixture was acidified with HCl and extracted with ethyl acetate. The extract was dried and concentrated to give the titled compound (32.31 g) as a colorless solid. 1H-NMR (CDCl3) delta: 3.96 (3H, s), 7.15-7.30 (2H,m), 7.75-7.97(3H,m), 8.26 (1H,s), 10.10 (1H,s). IR (KBr): 2841, 1688, 1624, 1480, 1269, 1028, 856 cm-1.

The synthetic route of 5111-65-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6420375; (2002); B1;,
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Related Products of 25245-34-5, The chemical industry reduces the impact on the environment during synthesis 25245-34-5, name is 2-Bromo-1,4-dimethoxybenzene, I believe this compound will play a more active role in future production and life.

Example 7: Preparation of 4,4′-dibromo-2,2′,5,5′- tetramethoxybiphenyl (7); [00113] In a 100 ml round-bottom flask, 3.0 g of FeCI3 in 20 ml of CH2CI2 was added to a solution of 5.0 g of 2,5-dimethoxybromobenzene in 50 ml of CH2CI2. The reaction mixture was stirred overnight, and then it was washed with water and brine and dried with magnesium sulfate. The solvent was removed on a rotary evaporator and the residue was purified by column chromatography eluted by hexane/CH2CI2 (3:1) to obtain 3.4 g of 4,4′- dibromo-2,2′,5,5′-tetramethoxybiphenyl (yield 68%) 1HNMR (CDCI3) 57.194 (s, 2 H), 6.841 (s, 2 H), 3.877 (s 3 H), 3.757 (s, 3 H).

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, 2-Bromo-1,4-dimethoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; NATIONAL UNIVERSITY OF SINGAPORE; WO2006/93467; (2006); A1;,
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Synthetic Route of 36942-56-0,Some common heterocyclic compound, 36942-56-0, name is 2-Bromo-4-methoxy-1-methylbenzene, molecular formula is C8H9BrO, 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: To a solution of compound 11 (100 mg, 0.21 mmol) and 3-methoxybenzeneboronic acid (49 mg, 0.32 mmol) in dioxane (5 mL) and H2O (0.5 mL) was added Na2CO3 (44 mg, 0.42 mmol) and LiCl (18 mg, 0.42 mmol). Under Ar, Pd(PPh3)4 (24 mg, 0.021 mmol) was added. The mixture was stirred for 12 h at 85C. Water was added. The resulting solution was extracted with ethyl acetate and washed with water and brine. The organic solution was dried over sodium sulfate, concentrated in vacuo. The residue was purified by silica gel chromatography (petroleum/ethyl acetate 5:1) to give 67 mg of 12 (yield: 75%) as a colorless liquid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-4-methoxy-1-methylbenzene, its application will become more common.

Reference:
Article; Huang, Jing; Guo, Bin; Chu, Wen-Jing; Xie, Xin; Yang, Yu-She; Zhou, Xian-Li; Chinese Chemical Letters; vol. 27; 1; (2016); p. 159 – 162;,
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Application of 59557-91-4, A common heterocyclic compound, 59557-91-4, name is 4-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.

Step A:To a round bottom flask at room temperature, containing formic acid (85%, 27 rrsL, 624.4 mmoi) was added acetic anhydride (16 mL, 169.5 mmoi) dropwise. The reaction stirred for 45 min. followed by the dropwise addition of a solution of 4-bromo- 2-methoxyaniline (9.01 g, 44.6 mmoi) in THF (56 mL). The reaction mixture was quenched with ice-water after 23 h and the resulting precipitate was filtered to afford compound 100.1 (9.20 g, 90%) as a brown 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; SCHERING CORPORATION; WO2009/76352; (2009); 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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, A new synthetic method of this compound is introduced below., Recommanded Product: 54314-84-0

The reaction mixture of 28 (0.50 g, 1.5 mmol) and [(3-bromopropoxy)methyl]benzene (32) (0.44 ml, 2.5 mmol) in dry 1,4-dioxane (16 ml) was stirred for 5 days to afford the title compound as a white solid in 73% yield (0.62 g). mp: 228-229 C; 1H-NMR (400 MHz, DMSO-d6): delta = 7.27-7.40 (m, 15H), 6.76 (s, 1H), 5.21 (br, 1H), 4.46 (s, 2H), 3.85 (m, 1H), 3.46 (t, J = 5.8 Hz 2H), 3.21-3.39 (m, 6H), 3.03 (m, 1H), 2.25 (m, 1H), 1.49-1.95 (m, 6H); 13C-NMR (500 MHz, DMSO-d6): delta = 172.8, 158.9, 143.6, 143.5, 130.1, 128.5, 128.4, 128.2, 128.1, 127.6, 127.5, 121.1, 115.0, 81.3, 69.1, 67.0, 63.0, 59.8, 54.1, 53.2, 26.2, 23.9, 20.9, 19.0, 18.1; HRMS calcd. for C31H36N1O4 [M]+: 486.2644; found: m/z = 486.2663; HPLC (Method B): tR (min) = 15.2 (98%).

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; Yamashita, Yasunobu; Tanaka, Ken-ichiro; Yamakawa; Asano; Kanda, Yuki; Takafuji; Kawahara, Masahiro; Takenaga, Mitsuko; Fukunishi, Yoshifumi; Mizushima; Bioorganic and Medicinal Chemistry; vol. 27; 15; (2019); p. 3339 – 3346;,
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