Tag: M.W=200-300

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 31804-36-1 as follows. Recommanded Product: 1-Bromo-3-methoxy-2-methylbenzene

A solution of 7g3, (9.3 g, 46 mmol), N-bromosuccinimide (8.2 g, 46 mmol) and benzoyl peroxide (450 mg, 1.8 mmol) in CCI4 (100 mL) is heated to reflux and stirred for 6 h. The reaction mixture is cooled to RT, and then filtered. The filtrate is diluted with DCM and washed successively with 2.0 N NaOH, water and brine. The organic layer is dried over MgS04, filtered and concentrated under vacuum to give 7g4.

According to the analysis of related databases, 31804-36-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; SIMONEAU, Bruno; DEROY, Patrick; FADER, Lee; FAUCHER, Anne-Marie; GAGNON, Alexandre; GRAND-MAITRE, Chantal; KAWAI, Steven; LANDRY, Serge; MERCIER, Jean-Francois; RANCOURT, Jean; WO2011/100838; (2011); A1;,
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Application of 867288-00-4, These common heterocyclic compound, 867288-00-4, name is 3,5-Difluoro-3′-methoxy-[1,1′-biphenyl]-4-amine, 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.

Procedure -1A solution of an anhydride (1.3 eq.) and an amine (1 eq) were dissolved in dioxane and refluxed overnight. Dioxane was evaporated and the resultant residue dissolved in AcOEt and extracted into aq. 2N NaHC03 solution. The aqueous layer was acidified with aq. 2 HC1 to obtain a solid, which was filtered and dried to give the desired amide.Example 12-(3^-Difluoro-3′-methoxybiphenyl-4-yIcarbainoyI)berizoic acid:The title compound (52 mg) was obtained from intermediate 1 (150 mg, 0.64 mmol) and phthalic anhydride (189 mg) as a white solid. MJ: 168-173G te-NMR (delta ppm, DUSO- k, 400 MHz): 13.05 (s, 1H), 10.19 (s, 1H), 7.83 (d, J 7.4, 1H), 7.69-7.63 (m, 1H), 7.62-7.52 (m, 4H), 7.39 (t, / 7.9, 1H), 7.34-7.27 (m, 2H), 6.98 (d, / 6.8, 1H), 3.83 (s, 3H). MS (m z): 381.55 ([itf-H]”).

The synthetic route of 867288-00-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INCOZEN THERAPEUTICS PVT. LTD.; RHIZEN PHARMACEUTICALS SA; MUTHUPPALANIAPPAN, Meyyappan; BHAVAR, Prashnant, Kashinath; VISWANADHA, Srikant; VAKKALANKA, Swaroop, Kumar, V.S.; MERIKAPUDI, Gayatri, Swaroop; WO2011/138665; (2011); A1;,
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Some common heterocyclic compound, 19056-40-7, name is 4-Bromo-3-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. category: ethers-buliding-blocks

Example 57A (102mg, 0.50 mmol) was treated with concentrated HCl (10 mL), cooled to 0 C, treated with a solution OF NAN02 (45MG, 0.65 mmol) in H20 (5 mL), stirred at 0 C for 1 hour, treated with a solution of KI (249mg, 1.5 mmol) in H20 (5 mL), stirred overnight while warming to room temperature, and extracted with ethyl acetate. The extract was washed with H20 and 10% Na2S203, dried (MGS04), filtered, and concentrated to provide 147mg (94%) of the desired product. MS (ESI) m/e 332 (M+20) + ; LH NMR (300 MHz, DMSO-d6) 8 7.39 (d, J = 1. 87 Hz, 1H), 7.34 (d, J = 8. 11 HZ, 1H), 7.24 (dd, J = 8. 11,1. 87 HZ, 1H), 3.86 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19056-40-7, its application will become more common.

Reference:
Patent; ABBOTT LABORATORIES; WO2004/76424; (2004); A1;,
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Some common heterocyclic compound, 35896-58-3, name is 1,2,3,4-Tetramethoxy-5-methylbenzene, molecular formula is C11H16O4, 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: 1,2,3,4-Tetramethoxy-5-methylbenzene

Step 3a: Synthesis of 1-Bromo-2,3,4,5-tetramethoxy-6-methyl benzeneTo a stirred solution of l,2,3,4-tetramethoxy-5-methylbenzene (obtained in Step 2a) (1.60 g, 7.54 mmol) in DCM (50 mL), a solution of bromine (0.41 mL, 7.92 mmol) in DCM (15 mL) was slowly added, and the resulting mixture was stirred at room temperature for 1 h. Water was added, the organic layer was separated and washed with 1 M NaOH and brine. The combined organic layers were dried over sodium sulphate and concentrated to dryness to give the product as yellow oil (2.00 g, 91%).Yield: 91%. TLC: R/= 0.80 petroleum ether:EtOAc 90:10 v/v. Spectroscopic data were as those reported in the literature by Tremblay, M. S. et al, Org. Lett. 2005, 7, 2417

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 35896-58-3, its application will become more common.

Reference:
Patent; NICOX SCIENCE IRELAND; BLANGETTI, Marco; FRUTTERO, Roberta; GASCO, Alberto; GIORGIS, Marta; LAZZARATO, Loretta; ROLANDO, Barbara; ALMIRANTE, Nicoletta; STORONI, Laura; WO2015/155234; (2015); A1;,
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Application of 19056-40-7, These common heterocyclic compound, 19056-40-7, name is 4-Bromo-3-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.

To a stirred solution of 4-bromo-3-methoxyaniline (1 g, 4.98 mmol) in 3:2 toluene/water (10 mL) was added cyclopropylboronic acid (514 mg, 5.98 mmol), Pd(OAc)2 (56 mg, 0.25 mmol), PCy3 (140 mg, 0.5 mmol) and K3PO4 (3.18 g, 15 mmol) at room temperature. The mixture was stirred at 100° C. for 10 h. The solid was filtered and the filtrate concentrated in vacuo. Purification by silica gel chromatography (2-10percent ethyl acetate/hexanes) provided 4-cyclopropyl-3-methoxyaniline (200 mg, 25percent) as a brown solid. 1H NMR (300 MHz, CDCl3) delta 6.67 (d, J=7.8 Hz, 1H), 6.24-6.20 (m, 2H), 3.82 (s, 3H), 3.50 (brs, 2H), 2.02-1.95 (m, 1H), 0.85-0.79 (m, 2H), 0.57-0.51 (m, 2H)

The synthetic route of 19056-40-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; US2010/168094; (2010); A1;,
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Related Products 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 4 4-bromo-2-methoxy-5-nitroaniline (compound 12-6) Potassium nitrate (217 mg, 2.25 mmol) was added to a solution of compound 12-5 (400 mg, 2.0 mmol) in 3.5 ml of concentrated sulfuric acid at -20 C., and vigorously stirred at -20 C. for 5 min. After completion of the reaction, the reaction mixture was diluted with water, extracted with EA/water system, washed with water for three times, and dried, and the organic layer was concentrated under reduced pressure to give the crude product compound 12-6 (300 mg) which was used directly in the next step. MS m/z (ESI): 246.9 [M+H]+.

The synthetic route of 59557-91-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHANGHAI HAIYAN PHARMACEUTICAL TECHNOLOGY CO. LTD.; YANGTZE RIVER PHARMACEUTICAL GROUP CO., LTD.; LAN, Jiong; JIN, Yunzhou; ZHOU, Fusheng; XIE, Jing; SHEN, Sida; HU, Yi; LIU, Wei; LV, Qiang; (96 pag.)US2017/8889; (2017); A1;,
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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. 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C13H11BrO

A degassed mixture of 3-benzyloxy-phenyl bromide (28) (0.176 g, 0.67 mmol), 3- methoxycarbonylphenylboronic acid (0.18 g, 1 mmol), barium hydroxide (0.25 g, 1.47 mmol), Pd(PPh3)4 (0.077 g, 0.067 mmol), DME (5 mL) and H2O (3 mL) was microwaved with vigorous stirring using a CEM-discover system (ram time: 2min, hold time: 5min, temperature: 120C, pressure: 200 psi, power: 250 W). The crude reaction mixture filtered through a plug of celite and concentrated in vacuo. The residue obtained was purified by flash column chromatography (25% diethyl ether-hexane) to give the title compound (29) (0.118 g, 60% yield) as a viscous liquid.[0280] 29 was confirmed as follows: 1H NMR (500 MHz, CDCl3) delta 8.27 (t, J = 1.5 Hz, 1H), 8.20 (dd, J = 8.0 Hz, J = 1.5 Hz, 1H), 7.76 (dd, J = 8.0 Hz, J = 2.0 Hz, 1H), 7.50 (t, J = 8.0 Hz, 1H), 7.47 (d, J = 7.5 Hz, 2H), 7.42-7.32 (m, 4H), 7.25-7.22 (m, 2H), 7.00 (dd, J = 8.2 Hz, J = 2.0 Hz, 1H), 5.13 (s, 2H), 3.95 (s, 3H).

The synthetic route of 53087-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NORTHEASTERN UNIVERSITY; WO2009/52319; (2009); A1;,
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Adding a certain compound to certain chemical reactions, such as: 22094-18-4, name is 1,3-Dibromo-2,2-dimethoxypropane, 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 22094-18-4, name: 1,3-Dibromo-2,2-dimethoxypropane

A suspension of NaH (110 g, 4580.1 mmol) in DMF (1.6 Lit) was cooled to 0 C, prior to the dropwise addition of 2-(3-fluorophenyl)acetonitrile (206 g, 1526.7 mmol) over 2 h. Reaction mixture was brought to rt and stirred for 45 min. To this mixture was added l,3-dibromo-2,2-dimethoxypropane (200 g, 763.3 mmol) in one portion at RT and stirring was continued at RT for 16 h, before heating at 80 C for 3 h. The reaction mixture was cooled to 0 C and quenched with crushed ice water (500 mL) and diluted with water (2.5 L), extracted with ethyl acetate (2×2 L). The combined organic layer was washed with brine solution (3×3 L), dried over Na2S04, filtered and the filtrate was concentrated. The crude compound was purified by silica gel column chromatography (100-200 mesh), eluting with 2-3% ethyl acetate in pet-ether to afford 114 g (63%) of l-(3- fluorophenyl)-3,3-dimethoxycyclobutanecarbonitrile (INT-27) as a colorless liquid (TLC system: 15%o ethyl acetate in pet ether; Rf: 0.4).

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, 1,3-Dibromo-2,2-dimethoxypropane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GRUeNENTHAL GMBH; RATCLIFFE, Paul; KONETZKI, Ingo; SITNIKOV, Nikolay; KOCH, Thomas; JOSTOCK, Ruth; (121 pag.)WO2019/12037; (2019); A1;,
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Synthetic Route of 36805-97-7,Some common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, molecular formula is C11H25NO2, 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 of ferf-butyl l-(3-chloropropy arboxylate; [0248] Indole-2-carboxylic acid (1 g, 3.71 mmol, 1 equiv) was suspended in toluene and the mixture was heated to refluxing temperatures. NN-dimethylformamide di-teri-butyl acetal (5.476 ml, 22.84 mmol, 4 equiv) was added dropwise to the refluxing mixture within 30 minutes.Refluxing was continued for an additional 30- 45 minutes after which it was cooled and stirred at ambient temperature for 16 h. The reaction was diluted with ether and the organic layer was washed with sodium bicarbonate (sat), water and brine. The ether layer was dried over MgSO i, filtered, concentrated in vacuo and purified using the Biotage flash chromatography system (SNAP 50g cartridge, R/= 0.4, gradient – 1 %-10% ethyl acetate in hexanes) to afford the tert-butyl lH-indole-2- carboxylate as a white powder (1.15 g, 86.8%); MS for Ci3H15N02 m/z 217.99 (M+H)+.

The synthetic route of 36805-97-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALTOS THERAPEUTICS, LLC; LUEHR, Gary, W.; SUNDARAM, Arathi; JAISHANKAR, Priyadarshini; PAYNE, Philip, W.; DRUZGALA, Pascal; WO2011/160084; (2011); A1;,
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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 332-48-9 as follows. HPLC of Formula: C8H8BrFO

Synthesis of example SC-51:Step 1: [3-(4-Chlorophenyl)-1 -[2-(4-fluoro-phenoxy)-ethyl]-4-methyl-5-(trifluoromethyl)-1 Hpyrrol-2-yl]-morpholin-4-yl-methanone (SC-51)(3-(4-Chlorophenyl)-4-methyl-5-(trifluoromethyl)-1 H-pyrrol-2-yI)(morpholino)methanone [for synthesis see SC-25] (130 mg, 0.349 mmol) was dissolved in dry MeCN (4 mL). The solution was mixed with K2C03 (120 mg, 0.872 mmol) and KI (8.7 mg, 0.052 mmol), followed by addition of 4-fluorophenoxy- ethylbromide (153 mg, 0.697 mmol). The reaction mixture was stirred vigorously at 80 C for 2 d. The temperature was lowered to room temperature; the reaction mixture was combined with the reaction mixture of another identical reaction (starting from 20 mg or 0.054 mmol (3-(4-chlorophenyl)-4-methyl- 5-(trifluoromethyl)-1 H-pyrrol-2-yl)(morpholino)methanone), followed by concentration in vacuo. The residue was used for flash chromatography (silica, gradient heptane/EtOAc, 1:0 -* 1:1). The product was purified by preparative TLC (silica, DCM twice) to result in 60 mg (29%) of SC-51.

According to the analysis of related databases, 332-48-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GRUeNENTHAL GMBH; SCHUNK, Stefan; REICH, Melanie; STEINHAGEN, Henning; DAMANN, Nils; SKONE, Philip; HAMLYN, Richard; KIRBY, Robert; ROGERS, Marc; SUTTON, Kathy; WO2014/32801; (2014); A1;,
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