Author: Jessica.F

Electric Literature of 10103-06-7,Some common heterocyclic compound, 10103-06-7, name is 2,3-Dimethoxynaphthalene, molecular formula is C12H12O2, 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) 2,3-Dimethoxy-naphthalene-1-carbaldehyde n-Butyl lithium in hexane (1.6 N, 31.3 ml) was gradually added to a solution of 2,3-dimethoxynaphthalene (9.4 g) and N,N,N’,N’-tetramethylethylenediamine (7.4 ml) in ether (150 ml) under argon at 0 C. The reaction mixture was stirred at room temperature for two hours, cooled to 0 C. and DMF (7.3 g) in ether (20 ml) added. The reaction mixture was stirred at room temperature overnight and poured in ice water. The product was extracted with ether, washed with water, dried, evaporated and recrystallized from ether. Yield: 4.2 g. 1H-NMR (DMSO-d6, 400 MHz): 10.68 (s,1H, CHO), 8.95-8.97 (m, 1H), 7.87-7.89 (m,1H), 7.80 (s,1H), 7.49-7.51 (m,2H), 4.00 (s,6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,3-Dimethoxynaphthalene, its application will become more common.

Reference:
Patent; Baeckstroem, Reijo; Pystynen, Jarmo; Lotta, Timo; Ovaska, Martti; Taskinen, Jyrki; US2004/34011; (2004); A1;,
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Reference of 702-24-9, These common heterocyclic compound, 702-24-9, name is 4-Methoxy-N-methylbenzylamine, 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.

Place ethyl 6,8-dichloroimidazo[ 1 ,2-bj pyridazine-3 -carboxylate (3 g, 11.54mmol), 1-(4-methoxyphenyl)-N-methylmethanamine (2.267 g, 15.00 mmol), and N,NDiisopropylethylamine (DIPEA) (4.03 mL, 23.07 mmol) in a 100 mL round bottle flask along with THF (15 mL). It was sealed and heated to 80¡ãC for 6 hours. The reactionmixture was concentrated and purified with silica gel chromatography. The product came out when eluting with 35percent ethyl acetate in hexane. The fractions containing product was collected and concentrated to provide the product (3.7 g, 9.87 mmol, 86percent yield, 100percentpurity). LC retention time 1.06 mm [Al. MS (ES+) m/z: 375 (MH). ?H NMR (400MHz, CHLOROFORM-d):8.14 – 8.09 (m, 1H), 7.20 – 7.13 (m, 2H), 6.89 – 6.83 (m, 2H), 6.11 (s, 1H), 5.49 (s, 2H),4.44 (q, J=7.2 Hz, 2H), 3.84 – 3.77 (m, 3H), 3.17 (s, 3H), 1.42 (t, J=7.2 Hz, 3H)

Statistics shows that 4-Methoxy-N-methylbenzylamine is playing an increasingly important role. we look forward to future research findings about 702-24-9.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WEINSTEIN, David S.; DUNCIA, John V.; SPERGEL, Steven H.; (76 pag.)WO2018/93968; (2018); A1;,
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Related Products of 74137-36-3, 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. 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

Step 3: Pd(PPh3)4 (600 mg, 0.53 mmol, 0.1 eq.) and Cs2CO3 (3.40 g,10.52 mmol, 2.0 eq.) were added to a stirred solution of N-(5-(4,4,5,5- tetramethyl-1 ,3,2-d ioxaborolan-2-yl)-pyridi n-2-yl)-2-methylpyri midi ne-5-carboxamide (1 .78 g, 5.26 mmol, 1 .0 eq.) and dibromoanisole (1 .40 g, 5.26 mmol, 1.0 eq.) in dioxane (14 ml) at RT under a nitrogen atmosphere. The reaction mixture was heated to 100 ¡ãC for 16 h after which time it was allowed to cool to RT. The reaction mixture was then filtered and the filtrate was concentrated under reduced pressure. The residue was diluted withethyl acetate (100 mL) and washed with water and brine (100 mL each). The organic layer was dried over Na2504 and concentrated under reduced pressure to give crude product. This material was purified by flash chromatography (over silica gel 230-400 mesh) eluting with 2 percent methanol in DCM to afford pure N-[5-(3-bromo-5-methoxyphenyl)pyridin-2-yl]-2-methylpyrimidine-5-carboxamide (1.20 g; 57percent).

The chemical industry reduces the impact on the environment during synthesis 1,3-Dibromo-5-methoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; FROST BIOLOGIC, INC.; SIDDIQUI-JAIN, Adam; WO2015/127284; (2015); A2;,
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Adding a certain compound to certain chemical reactions, such as: 321-28-8, name is 1-Fluoro-2-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 321-28-8, Recommanded Product: 321-28-8

Step 1: Preparation of 3′-fluoro-4′-methoxy-acetophenone. Acetyl chloride (51.0 g, 0.65 mol) was added dropwise to a stirred solution of aluminum chloride (80.0 g, 0.6 mol) and chloroform (750 mL), maintaining the temperature between 5-10 C. The mixture was stirred for 10 minutes at 5 C before the dropwise addition of 2-fluoroanisole (62.6 g, 0.5 mol). The mixture was stirred at 0-10 C. for 1 hour and poured into ice (1 L). The resultant layers were separated and the aqueous layer was extracted with dichloromethane (2*250 mL). The combined organic layers were washed with water (2*150 mL), dried over anhydrous MgSO4, filtered and concentrated in vacuo to a volume of 300 mL. Hexanes were added and a white solid formed which was isolated by filtration and air dried. This material was recrystallized from a mixture of dichloromethane and hexanes to afford material suitable for use in the next step (77.2 g, 92%): mp 92-94 C.

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; G.D. Searle & Co.; US6407140; (2002); B1;,
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Synthetic Route of 53087-13-1, The chemical industry reduces the impact on the environment during synthesis 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, I believe this compound will play a more active role in future production and life.

General procedure: Under a nitrogen gas atmosphere, 3-bromoanisole(35 mL, 277 mmol) was added dropwise to a mixtureof magnesium (7.1 g, 292 mmol) and a catalytic amount ofiodine in tetrahydrofuran (THF) (270 mL), and the mixturewas stirred for 2 h. This reaction solution was added dropwiseto a solution of tert-butyl (2S)-2-{[methoxy(methyl) amino]-carbonyl}piperidine-1-carboxylate (8, 50.0 g, 184 mmol) inTHF (300 mL) under ice cooling, and the mixture was stirredat room temperature for 2 h. Ten percent aqueous NH4Cl solutionwas added, followed by extraction with EtOAc. Theorganic layer was washed with water and brine, dried overanhydrous Na2SO4, filtered, and concentrated in vacuo. Theresidue was purified using silica gel column chromatography(11% EtOAc in hexane) to yield 9c (32.7 g, 56%) as a pale yellowoil.

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-(Benzyloxy)-3-bromobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Yamamoto, Shuji; Shibata, Tsuyoshi; Abe, Kumi; Oda, Koji; Aoki, Takeshi; Kawakita, Yasunori; Kawamoto, Hiroshi; Chemical and Pharmaceutical Bulletin; vol. 64; 9; (2016); p. 1321 – 1337;,
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Synthetic Route of 104197-14-0, 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. 104197-14-0, name is 4-Bromo-2,6-difluoroanisole belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Preparation 14. 2-r3,5-difluoro-4-(methyloxy)phenylH,4,5,5-tetramethyl-1.3,2- dioxaborolane; A solution of 4-bromo-2,6-difluoroanisole (223mg, 1 mmole), bis(pinacaolato)diboron (275 mg, 1.09 mmole), [1 ,1 ‘-bis(diphenylphosphino)ferrocene]dichloropalladium(ll) (40 mg) and KOAc (300 mg) in 5 ml of dioxane was heated in the microwave at 150 for 20 minutes. The reaction was diluted with H2O and extracted with Et2O. The extracts were washed with H2O, dried and evaporated. The residue was chromatographed on a Florisil column, and the titled compound was eluted with Et20, 158 mg (58%). 1H NMR (400 MHz, CDCI3) delta 7.32 (d, J=8Hz, 2H), 4.05 (s, 3H), 1.35 (s, 12H).

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-2,6-difluoroanisole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/63167; (2006); A1;,
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Reference of 944317-92-4,Some common heterocyclic compound, 944317-92-4, name is 1-Bromo-4-fluoro-5-isopropyl-2-methoxybenzene, molecular formula is C10H12BrFO, 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.

Argon gas is continuously fed into a 2L three-neck flask equipped with a mechanical stirrer, a Y-shaped tube, and a thermometer.10-0.9 g of 1-bromo-4-fluoro-5-isopropyl-2-methoxybenzene, 324 mL of tetrahydrofuran, 324 mL of toluene, and 130 mL of triisopropyl borate. The system was cooled down to -80 to -70C, and 253 mL of 2mol/L n-butyllithium was added dropwise to the system. The temperature drop was -80 to -70C. The addition was completed.After the incubation -80 ~ -70 C reaction 3h.The reaction solution was slowly poured into 1000 mL of dilute hydrochloric acid with a concentration of 1.2 M, and methyl tert-butyl ether (300 mL) was added. After stirring for 10 min, the mixture was allowed to stand for 5 min, and the aqueous phase was extracted with 500 mL of methyl tert-butyl ether. 10 min, stand for 5 min, and combine the organic phases. Add 1.0 L of 1M aqueous sodium hydroxide solution while stirring the organic phase, stirring10min, let stand 5min liquid.The organic phase obtained by liquid separation was further added with 300 mL of aqueous sodium hydroxide solution, stirred for 10 minutes, and allowed to stand for 5 minutes to separate liquids, and the organic phase was temporarily stored.Combine the aqueous phase, temperature control 0 ~ 15 C, with concentrated hydrochloric acid about 160mL adjust the system to pH = 1 ~ 2, temperature 0 ~ 15 C stirring 0.5h, filtration, filter cake rinse with water, bake to constant weight to give a white solid 4-(4-Fluoro-5-isopropyl-2-methoxyphenyl)boronic acid, 71.63 g (yield of 82.71%,4-Fluoro-5-isopropyl-2-methoxyphenyl)boronic acidLC = 99.68%,

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-4-fluoro-5-isopropyl-2-methoxybenzene, its application will become more common.

Reference:
Patent; Xi’an Ruilian New Materials Co., Ltd.; Yan Longjia; Yu Xinmin; Wang Xiaoming; Wang Xiaowei; He Hanjiang; (9 pag.)CN107365324; (2017); A;,
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Synthetic Route of 18800-30-1, These common heterocyclic compound, 18800-30-1, name is 1-Bromo-4-(2-bromoethoxy)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.

Example IX b) 52.0 g (186 mmol) of 1-bromo-4-(2-bromoethoxy)benzene is added to 300 mL THF and cooled down to 0 C. Within 30 min 25.0 g (223 mmol) KOtBu are added to this mixture in several portions. Cooling is removed and the reaction mixture is stirred at r.t. over night. The reaction is quenched by the addition of water. The resulting mixture is extracted with EtOAc (2¡Á). The org. phases are combined, washed with sat. aq. NaCl solution, dried with MgSO4, filtered and the solvent is removed in vacuo. The resulting product is used without further purification.

Statistics shows that 1-Bromo-4-(2-bromoethoxy)benzene is playing an increasingly important role. we look forward to future research findings about 18800-30-1.

Reference:
Patent; FLECK, Martin; NOSSE, Bernd; ROTH, Gerald Juergen; US2013/172316; (2013); A1;,
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Related Products of 126-38-5,Some common heterocyclic compound, 126-38-5, name is 1-Bromo-2,2-dimethoxypropane, molecular formula is C5H11BrO2, 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 solution of 3j (0.360?g, 2.00?mmol) and 1-bromo-2,4-dimethoxypropane (11, 0.330?mL, 2.44?mmol) in acetic acid (4.0?mL) was stirred at reflux for 3?h. After the solution was cooled to room temperature and concentrated, it was diluted with EtOAc and washed with water and saturated NaHCO3(aq). The organic layer was dried over MgSO4(s), filtered, and concentrated to afford a residue, which was purified by Isco Combi-Flash Companion column chromatography (0-20% EtOAc in n-hexane) to give 12 (0.114?g, 26%) as a yellow solid. 1H NMR (CDCl3, 300?MHz) delta 7.57 (d, 1H), 7.27-7.20 (m, 2H), 7.11 (dd, 1H), 7.05 (br s, 1H), 6.13 (s, 1H), 2.66 (q, 2H), 2.28 (s, 3H), 1.23 (t, 3H); 13C NMR (CDCl3, 75?MHz) delta 167.32, 148.57, 138.25, 136.07, 129.23, 127.04, 125.08, 121.85, 101.53, 24.32, 17.23, 14.25; HPLC Purity?=?100%, tR?=?29.20?min; LC-MS (ESI) m/z: 219.0 [M + H]+; HRMS (ESI): m/z calculated for C12H15N2S [M + H]+: 219.0956 Found: 219.0950.

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

Reference:
Article; Lin, Shu-Yu; Kuo, Yu-Hsien; Tien, Ya-Wen; Ke, Yi-Yu; Chang, Wan-Ting; Chang, Hsiao-Fu; Ou, Li-Chin; Law, Ping-Yee; Xi, Jing-Hua; Tao, Pao-Luh; Loh, Horace H.; Chao, Yu-Sheng; Shih, Chuan; Chen, Chiung-Tong; Yeh, Shiu-Hwa; Ueng, Shau-Hua; European Journal of Medicinal Chemistry; vol. 167; (2019); p. 312 – 323;,
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Some common heterocyclic compound, 41365-75-7, name is 1-Amino-3,3-diethoxypropane, molecular formula is C7H17NO2, 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

3,3-diethoxypropan-1-amine (6 g, 40.76 mmol, 1.00 equiv) was dissolved in 1,4- dioxane (30 mL) in the presence of TEA (4.45 g, 43.98 mmol, 1.08 equiv), then cooled to0C. (Boc)20 (9.6 g, 43.99 mmol, 1.08 equiv) diluted in 20 mL of 1,4-dioxane was added drop-wise. The solution was agitated 2 hours at 0C then overnight at ambient temperature before being neutralised with 10 mL of water. The pH was adjusted to 5 with HC1 (1 %). The solution was extracted 3 times with 50 mL of EtOAc. The organic phases were combined, dried over sodium sulfate, filtered and concentrated to yield 8.21 g (81 %) of compound 1ZDin the form of a pale yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 41365-75-7, its application will become more common.

Reference:
Patent; PIERRE FABRE MEDICAMENT; JOUHANNEAUD, Alexandra; GOETSCH, Liliane; BROUSSAS, Matthieu; BEAU-LARVOR, Charlotte; CHAMPION, Thierry; ROBERT, Alain; HAEUW, Jean-Francois; RILATT, Ian; PEREZ, Michel; (244 pag.)WO2017/72196; (2017); A1;,
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