Tag: M.W=200-300

Electric Literature of 202865-80-3, 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 202865-80-3 as follows.

To a mixture of 2-amino-5-[3-(t-butyl)dimethyl-silanoxypropyloxy]-1-(4-methylbenzyl)benzene (54 mg, 0.14 mmol), 4-bromo-2-fluoro-1-isopropoxybenzene (32.6 mg, 0.14 mmol), dicyclohexylphosphino-2′,6′-diisopropoxy-1,1′-biphenyl (3.3 mg, 0.007 mmol), potassium t-butoxide (28.3 mg, 0.29 mmol) and toluene (2 mL) was added palladium acetate(II) (1.6 mg, 0.007 mmol) under nitrogen atmosphere, and the resulting mixture was stirred at 100C for 1 hour. The reaction mixture was concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give 1-(4-chlorobenzyl)-3-[3-(t-butyl)dimethyl-silanoxypropyloxy]-6-(3-fluoro-4-isopropoxy phenylamino)benzene (69 mg, Yield: 92%) as brown oil. 1H-NMR (delta ppm TMS/DMSO-d6): 0.00(6H, s), 0.84 (9H, s), 1.21 (6H, d, J = 6.0 Hz), 1.84 (2H, q, J = 6.0 Hz), 2.22 (3H, s), 3.70 (2H, t, J = 6.0 Hz), 3.80 (2H, s), 3.92 (2H, t, J = 6.0 Hz), 4.27 (1H, q, J = 6.0 Hz), 6.32-6.42 (2H, m), 6.62 (1H, d, J = 3.0 Hz), 6.75 (1H, dd, J = 2.4 Hz, 8.4 Hz), 6.84-6.94 (1H, m), 6.97-7.08 (5H, m), 7.25 (1H, s).

According to the analysis of related databases, 202865-80-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shionogi & Co., Ltd.; KAI, Hiroyuki; ENDOH, Takeshi; JIKIHARA, Sae; ASAHI, Kentaro; HORIGUCHI, Tohru; EP2604260; (2013); A1;,
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Some common heterocyclic compound, 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene, molecular formula is C7H5BrF2O, 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. name: 1-Bromo-4-(difluoromethoxy)benzene

A mixture of 1-bromo-4-(difluoromethoxy)benzene (230 mg, 1.05 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (402 mg, 1.58 mmol), PdCl2 (dppf) (20 mg), and Cs2CO3 (682 mg, 2.1 mmol) in dioxane was sealed in a microwave reaction cube and reacted at 180 C. for 2 hours in a microwave reactor. Then it was purified by flash column chromatography (PE/EA) to give the crude compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5905-69-1, its application will become more common.

Reference:
Patent; HUTCHISON MEDIPHARMA LIMITED; Su, Wei-Guo; Deng, Wei; Ji, Jianguo; US2014/121200; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1663-61-2, name is (Triethoxymethyl)benzene, 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 1663-61-2, Application In Synthesis of (Triethoxymethyl)benzene

To a suspension of triol 11 (3.0 g, 9.2 mmol) in dry MeCN (100 mL), camphor-10-sulfonic acid (880 mg, 3.7 mmol) and triethylorthobenzoate (8.2 mL, 38.6 mmol), were added. The mixture was stirred at rt for 12 h and Et3N (1.5 mL) was added to neutralize the solution. The mixture was then evaporated to dryness and the residue was diluted with DMF (100 mL). NaH (60percent dispersion in mineral oil, 542 mg, 18.4 mmol) was added at 0 °C followed by dropwise addition of BnBr (1.8 mL, 16.6 mmol). The reaction mixture was stirred at rt for 2 h and the excess of sodium hydride was neutralized by dropwise addition of MeOH (20 mL) at 0 °C. The mixture was then evaporated to dryness and the residue was dissolved with EtOAc. The organic phase was washed with water and then with 2 M aqueous HCl (.x.3). The opening of the orthoester was checked by TLC. The organic phase was dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography using cyclohexane/EtOAc (98:2–>9:1) as eluent to give 5 (2.2 g, 46percent) and its beta-anomer 2-methyl-5-tert-butylphenyl 2-O-benzoyl-4-O-benzyl-1-thio-beta-l-rhamnopyranoside (340 mg, 7percent) as colorless oils. (alpha anomer) Rf 0.42 (cyclohexane/EtOAc 8:2); [alpha]D -93 (CHCl3, c 0.7); 1H NMR (300 MHz, CDCl3) delta 8.24-7.27 (m, 13H, SC6H3C(CH3)3CH3, OCH2C6H5, OCOC6H5), 5.82 (dd, 1H, J1,2 = 1.3 Hz, J2,3 = 3.3 Hz, H-2), 5.66 (br s, 1H, H-1), 5.11 (d, 1H, JA,B = 11.2 Hz, A part of an AB system, OCHHC6H5), 4.93 (d, 1H, JA,B = 11.2 Hz, B part of an AB system, OCHHC6H5), 4.55-4.43 (m, 2H, H-3, H-5), 3.78 (t, 1H, J3,4 = J4,5 = 9.2 Hz, H-4), 2.59 (s, 3H, SC6H3C(CH3)3CH3), 1.59 (d, 3H, J5,6 = 5.9 Hz, H-6), 1.46 (s, 9H, SC6H3C(CH3)3CH3); 13C NMR (75 MHz, CDCl3) delta 166.4 (OCOC6H5), 149.8, 138.4, 137.0, 133.5, 133.0, 132.9, 130.2, 130.1, 130.0, 129.7, 128.7, 128.6, 128.5, 128.3, 128.1, 127.6, 125.2, 124.0, (SC6H3C(CH3)3CH3, OCOC6H5, OCH2C6H5) 85.8 (C-1), 81.8 (C-2), 75.6 (C-4), 75.3 (OCH2C6H5), 71.3 (C-3), 69.0 (C-5), 34.6 (SC6H3C(CH3)3CH3) 31.5 (SC6H3C(CH3)3CH3), 20.5 (SC6H3C(CH3)3CH3), 18.3 (C-6); HR-ESI-MS m/z calcd for C31H36O5S 543.2175 [M+Na]+, found 543.2160.

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, (Triethoxymethyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Conference Paper; Milhomme, Ophelie; Dhenin, Sandrine G.Y.; Djedaini-Pilard, Florence; Moreau, Vincent; Grandjean, Cyrille; Carbohydrate Research; vol. 356; (2012); p. 115 – 131;,
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Adding a certain compound to certain chemical reactions, such as: 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, 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 74137-36-3, Application In Synthesis of 1,3-Dibromo-5-methoxybenzene

2 mmol 3,5-dibromoanisole were dissolved in 10 ml THF and cooled to -78C. 2.4 mmol of n- BuLi were added dropwise and stirring was continued for 15 min. 3 mmol of methyl iodide were added and the mixture was allowed to slowly warm to ca. -200C over a period of ca. 2 h. IM HCl and dichloromethane were added and the phases were separated. 1.65 mmol of crude 3-bromo-5- methylanisole were taken to the next step without further purification.

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; KARO BIO AB; WO2008/43567; (2008); A1;,
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Related Products of 17061-62-0, A common heterocyclic compound, 17061-62-0, name is Bis(4-methoxybenzyl)amine, molecular formula is C16H19NO2, 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 solution of bis(4-methoxybenzyl)amine 30.1 (900 g, 3.49 mol, 1 eq) in DCM (9 L) was added TEA (634 mL, 4.55 mol, 1.3 eq), followed by dropwise addition of ethanesulfonyl chloride (399 mL, 4.19 mol, 1.2 eq). (The internal temperature was kept between 5-10 C during the addition of the ethane sulfonyl chloride). Once the addition was complete, the cooling bath was removed. After 1.5 h, TLC showed complete loss of starting material. The reaction was quenched by the addition of water (4 L) to the reaction mixture. The layers were separated and the aqueous layer was extracted with DCM (2x 2 L). The combined organic layers were washed with brine (2x 1 L), dried over Na2SO4, and concentrated in vacuo. The material thus obtained was adsorbed onto a plug of silica gel and purified by chromatography (silica gel (60-120 mesh) eluting with a gradient of 10- 80% EtOAc in hexanes) to provide the title compound 30.0 (1125 g, 3.22 mol, 92%) as a white solid. 1H-NMR (400 MHz, CDCl3) delta 7.23 (dd, J = 2.08, 6.62 Hz, 4H), 6.90 (dd, J = 2.12, 6.60 Hz, 4H), 4.29 (s, 4H), 3.83 (m, 6H), 2.92 (q, J = 7.40 Hz, 2H), 1.33 (t, J = 7.40 Hz, 3H). GC-LCMS (ESI pos. ion) m/z: = 372.2 (M+Na)+.

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; AMGEN INC.; CHEN, Yinhong; CHENG, Alan C.; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; HARVEY, James S.; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; LAI, Su-Jen; MA, Zhihua; PATTAROPONG, Vatee; SWAMINATH, Gayathri; KREIMAN, Charles; MOEBIUS, David C.; SHARMA, Ankit; (543 pag.)WO2018/93580; (2018); A1;,
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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. 16618-68-1, name is 3-Bromo-5-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 3-Bromo-5-methoxyaniline

To a solution of 5-bromo-3-(2-fluoropyridin-4-yl)-4-methyl-1-tosyl-1H-pyrrolo[2,3-b]pyridine from step 3 (258 mg, 0.56 mmol) in 1,4-dioxane (5 mL) was added potassium acetate (165 mg, 1.68 mmol), bis(pinacolato) diboron (569 mg, 2.24 mmol) and bis(diphenylphosphino)ferrocene]dichloropalladium(II).DCM (23 mg, 0.028 mmol). The solution was treated with microwave radiation at 130 C. for 3.5 hours. To this solution was added 3-bromo-5-methoxyaniline (113 mg, 0.56 mmol), potassium carbonate (232 mg, 1.68 mmol) and bis(diphenylphosphino)ferrocene]dichloropalladium(II).DCM (23 mg, 0.028 mmol). The solution was treated with microwave radiation at 120 C. for one hour. After cooling the resulting solution was partitioned between ethyl acetate and water. The organic layer was washed with water, brine and dried over magnesium sulfate. The mixture was filtered and concentrated in vacuo. The crude material was purified using normal phase chromatography (ethyl acetate/heptane) to provide 3-(3-(2-fluoropyridin-4-yl)-4-methyl-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-5-methoxyaniline (154 mg, 55% yield): MS (ES) m/z 503 (M+H).

According to the analysis of related databases, 16618-68-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jacobsen, Eric Jon; Blinn, James Robert; Springer, John Robert; Hockerman, Susan L.; Anderson, David Randolph; (120 pag.)US2018/208594; (2018); A1;,
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Application of 20469-65-2,Some common heterocyclic compound, 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, molecular formula is C8H9BrO2, 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.

The Pd-catalyzed cross-coupling reaction of 5-Bromo-l,3-dimethoxybenzene with allyl boronic acid pinacol ester produced 5-allyl~l,3-dimethoxybenzene 1 in excellent yield; Example 20 Synthesis of 5-AUyl-l,3-dimethoxybenzene5-Bromo-l,3-dimethoxybenzene (2.13 g, 9.8 mralphaol), CsF (2.88 g, 19.0 mmol), and Pd(Ph3)4 (0.57-1.13 g, 0.5-1.0 mmol) were weighed into a flame-dried Schlenk flask and put under a flow of argon. THF (80 mL) was added to the flask via syringe, and the resulting suspension was stirred for 30 min at room temperature. AHyI boronic acid pinacol ester (2.96 g, 17.6 mmol) in THF (40 ml) was added and the resulting mixture was heated to reflux for 30 h. Another portion of CsF (2.88 g, 19.0 mmol) and Pd(Ph3)4 (0.57-1.13 g, 0.5-1.0 mmol) were added and the reaction was continued to reflux for 24 h. The reaction mixture was diluted with petroleum ether (100 ml) followed by H2O (100 ml). The layers were separated and the aqueous layer was extracted with petroleum ether (2 x 80 ml). The combined organic layers were washed with H2O (100 ml), and brine (100 ml). The solution was dried over MgSO4 and evaporated to dryness. The crude product was purified by column chromatography (silica, eluent: hexanes/benzene = 3:2) to give 1.60 g (92%) of 5-Allyl-l,3- dimethoxybenzene. 1H NMR (CDCl3): delta 3.33 (d, J = 6.7 Hz, 2H, CH2CH=CH2), 3.77 (s, 6H, OCHi), 5.02-5.11 (m, 2H5. CH2CH=CH2), 5.89-5.99 (m, 1Eta, CH2CH=CH2), 6.33-6.38 (m, 3H).

The synthetic route of 20469-65-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; RUTERGS UNIVERSITY; WO2007/8847; (2007); A2;,
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Electric Literature of 29578-83-4, These common heterocyclic compound, 29578-83-4, name is 1-Bromo-3-methoxy-5-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.

To a vigorously stirred mixture of 1 -Bromo-3-methoxy-5-methylbenzene (1 g, 4.97 mmol), Pyridine (3.22 mL, 39.8 mmol) and Water (8 ml) was added in small portions KMn04 (3.14g, 19.89 mmol) at 105C. The mixture which turned to a black suspension was stirred 24 hours at 105C, then cooled down to RT and filtered over Hyflo. The black residue was washed several times with EtOAc. The filtrate was then diluted in EtAOc and washed with a 2M solution of HCI. The organic layer was dried over sodium sulfate, filtered and concentrated to afford the title compound (281 mg, 24% yield) as a white solid. MS: 229.1 [M+H]+, Rt (1 ) = 1 .18 min.

Statistics shows that 1-Bromo-3-methoxy-5-methylbenzene is playing an increasingly important role. we look forward to future research findings about 29578-83-4.

Reference:
Patent; NOVARTIS AG; COOKE, Nigel Graham; FERNANDES GOMES DOS SANTOS, Paulo Antonio; FURET, Pascal; HEBACH, Christina; HOeGENAUER, Klemens; HOLLINGWORTH, Gregory; KALIS, Christoph; LEWIS, Ian; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; STAUFFER, Frederic; STRANG, Ross; STOWASSER, Frank; TUFILLI, Nicola; VON MATT, Anette; WOLF, Romain; ZECRI, Frederic; WO2013/88404; (2013); A1;,
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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. 59557-91-4, name is 4-Bromo-2-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 59557-91-4

Intermediate 10 4-Bromo-2-methoxy-N /V-dimethylaniline [00406] Formaldehyde (3.7 mL, 49 mmol, 37% aqueous) and acetic acid (57 uL, 1 mmol) were added to a solution of 4-bromo-2-methoxyaniline (2.0 g, 9.9 mmol) in methanol (10 mL) at 25 C. The mixture was stirred for 2 h, and then sodium cyanoborohydride (3.11 g, 49.5 mmol) was added in portions. The resulting mixture was stirred for 12 h, poured into a saturated NaHC03 solution (40 mL), and then extracted with ethyl acetate (3 x20 mL). The combined organic phases were washed with brine (2×20 mL), dried over anhydrous Na2S04, filtered and concentrated. The residue was purified by column chromatography (Si02, petroleum ether/ethyl acetate; 15/1) to give 4-bromo-2-methoxy-N,N-dimethylaniline (2.0 g, 80%) as a brown oil. 1H MR (CDC13): delta 7.02 (dd, 1H), 6.95 (d, 1H), 6.78 (d, 1H), 3.87 (s, 3H), 2.76 (s, 6H); MS: 230.0 [M+H]+.

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 59557-91-4.

Reference:
Patent; METACRINE, INC.; SMITH, Nicholas D.; GOVEK, Steven P.; NAGASAWA, Johnny Y.; (228 pag.)WO2017/49172; (2017); A1;,
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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. 22094-18-4, name is 1,3-Dibromo-2,2-dimethoxypropane, This compound has unique chemical properties. The synthetic route is as follows., category: ethers-buliding-blocks

To a suspension of NaH (120 g , 3.0 mol) in DMF (1 L) was added dropwise diisopropyl malonate (507 g, 2.7 mol) under an Ar atmosphere, and the reactionwas stirred.Compound 29.2(360 g, 1.35 mol) was then added in portionsand the mixturewas heated to reflux for 48 hr.The reaction mixture was poured into water (2 L), and extracted with PE (6 x 1 L). The combinedorganic layers were dried, filteredand concentrated under reduced pressure 15 to give a yellow oil, which was purified by distillation under reduced pressureto yield compound 29.3 (150 g, 45%) as a colorless oil.

According to the analysis of related databases, 22094-18-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACHAOGEN, INC.; LINSELL, Martin Sheringham; AGGEN, James Bradley; DOZZO, Paola; HILDEBRANDT, Darin James; COHEN, Frederick; KASAR, Ramesh Annasaheb; KANE, Timothy Robert; GLIEDT, Micah James; MCENROE, Glenn A.; WO2014/165075; (2014); A1;,
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