Author: Jessica.F

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. 65896-11-9, name is 2-Bromo-6-fluoroaniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Bromo-6-fluoroaniline

Preparation of intermediate 3A:N-(4-bromophenyl)-4-fluorobenzothiazol-2-ylamine2-Bromo-6-fluoroaniline (500 mg, 2.63 mmol) and potassium carbonate (5726 mg, 5.26 mmol) were placed in a flask, to which was added 10 mL of DMSO. l-Bromo-4-thiocyanato-benzene (845 mg, 3.95 mmol) was added under nitrogen protection and resulting mixture was stirred at room temperature for 30 min. Cuprous iodide (50 mg, 0.263 mmol) was added and then heated to 120 C under nitrogen protection, and reacted overnight. The mixture was cooled to room temperature, poured into water to give a precipitate, which was filtered to give 383 mg of compound 3 A, which was used directly in the next step without further purification. Yield: 45.2%.MS (ESI, m/z): [M+H]+: 324.0

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; BEIJING HANMI PHARMACEUTICAL CO., LTD; ZHANG, Bo; YANG, Jun; LIU, Jinming; HUANG, Hai; WU, Yong; TAO, Ran; XU, Jiangcheng; SHEN, Ning; MOON, Sunghwan; KIM, Maengsup; WO2013/56679; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 937046-98-5, 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. 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a stirred suspension of 7-bromopyrrolo[2,1-f][1,2,4]triazin-4-ylamine (0.372 g, 1.745 mmol) in THF (8mL) was added TMS-Cl (0.446 ml, 3.49 mmol) and the mixture was stirred at room temperature for 2 hours. The reaction was then cooled to -78 C. and n-BuLi (2.79 ml, 6.98 mmol) was added dropwise. The mixture was stirred at -78 C. for 1 hour and then Int 21h (0.69 g, 1.745 mmol) dissolved in THF (2 mL) was added dropwise. After 10 min at -78 C., the reaction mixture was allowed to warm up to 0 C. over 40 minutes. The reaction was quenched with aqueous ammonium chloride (15 mL) and then extracted with ethyl acetate (3×30 mL). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography using a gradient of 10-70% EtOAc in hexane to provide Int 21i as a mixture of isomers (240 mg).

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, 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck Sharp & Dohme Corp.; Girijavallabhan, Vinay; Njoroge, F. George; Bogen, Stephane; Bennett, Frank; Verma, Vishal; Arasappan, Ashok; Chen, Kevin X.; Huang, Ying; Kerekes, Angela; Nair, Latha; Pissarnitski, Dimitri; Dang, Qun; Davies, Ian; Olsen, David B.; Stamford, Andrew; Vacca, Joseph P.; US2014/206640; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 3814-30-0, These common heterocyclic compound, 3814-30-0, name is (Bromomethyl)cyclopentane, 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 2-1 -1 Preparation of 4-({2-[1 -(cyclopentylmethyl)-1 H-indazol-3-yl]-5-methoxypyrimidin-4- yl}amino)pyridine-3-carboxamide 100 mg of 4-{[2-(1 H-lndazol-3-yl)-5-methoxypyrimidin-4-yl]amino}pyridine-3- carboxamide 1 -8-1 (277 muiotaetaomicronIota, 1 .0 eq.), 34 muIota_ (bromomethyl)cyclopentane (300 muetaiotaomicronIota, 1 .1 eq.) and 50 muIota_ 1 ,8-Diazabicyclo(5.4.0)undec-7-en (330 muiotaetaomicronIota, 1 .2 eq.) were dissolved in 2.1 mL DMF and stirred at rt for 3 days. The reaction mixture was diluted with water and ethyl acetate and extracted three times. The organic layers were washed once with water and brine, filtered through a silicon coated filter and concentrated in vacuo. The crude product was purified by HPLC-chromatography under basic conditions to provide the 96% pure target compounds: 12 mg, 30 muiotaetaomicronIota, 10% 1 H-NMR (400MHz, DMSO-d6) : delta [ppm]= ]= 1 .37 – 1 .49 (m, 2H), 1 .49 – 1 .62 (m, 2H), 1 .63 – 1 .76 (m, 4H), 2.54 – 2.63 (m, 1 H), 4.07 (s, 3H), 4.47 (d, 2H), 7.23 – 7.33 (m, 1 H), 7.42 – 7.52 (m, 1 H), 7.78 (d, 1 H), 7.89 (br. s, 1 H), 8.42 – 8.51 (m, 3H), 8.56 (d, 1 H), 8.97 (S, 1 H), 9.32 (d, 1 H), 12.17 (s, 1 H).

The synthetic route of 3814-30-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; HITCHCOCK, Marion; MENGEL, Anne; MUeLLER, Thomas; BAeRFACKER, Lars; CLEVE, Arwed; BRIEM, Hans; SIEMEISTER, Gerhard; BONE, Wilhelm; FERNANDEZ-MONTALVAN, Amaury, Ernesto; SCHROeDER, Jens; MOeNNING, Ursula; HOLTON, Simon; PREUSSE, Cornelia; (165 pag.)WO2017/157991; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

1647-26-3, name is 1-Bromo-2-cyclohexylethane, belongs to bromides-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 1647-26-3

General procedure: To a solution of the corresponding hydroxyl indanone compound 7b-g (1.67mmol) in DMF (10mL), K2CO3 (3.35mmol) and appropriate alkyl or phenyl bromide (1.84mmol) were added. The resulting solution was stirred at 60C until complete conversion of the starting material (3h). After cooling to ambient temperature, the reaction mixture was concentrated under reduced pressure and diluted with ethyl acetate. The organic phase was washed with water, brine solution, dried over anhydrous Na2SO4, and then concentrated under reduced pressure. The residue was subjected to flash silica gel (230-400 mesh) column chromatography (eluting with 0-20% ethyl acetate in hexanes) to afford the title compounds.

The synthetic route of 1647-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Boggu, Pulla Reddy; Cho, Jungsuk; Kim, Youngsoo; Jung, Sang-Hun; European Journal of Medicinal Chemistry; vol. 152; (2018); p. 65 – 75;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 10016-52-1, These common heterocyclic compound, 10016-52-1, name is 2,8-Dibromodibenzo[b,d]furan, 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 1 L reaction flask was added toluene solvent (450 ml), 2,8-dibromodibenzofuran (11.74 g, 36 mmol),Intermediate I-11 (32.62 g, 90 mmol), Pd2 (dba) 3 (990 mg, 1.08 mmol),BINAP (1.65 g, 16.5 mmol) and sodium tert-butoxide (9.9 g, 100.8 mmol),Dissolved by stirring, and refluxed under nitrogen for 24 hours.After completion of the reaction, the reaction solution was washed with dichloromethane and distilled water and then evaporated.The organic layer was dried over anhydrous magnesium sulfate and filtered and evaporated.Separation and purification by column chromatography using cyclohexane:ethyl acetate=10:1 as eluent.Finally, solid compound 11 (24.00 g, yield 75%) was obtained, and the solid purity was determined to be 99.5% by HPLC.

Statistics shows that 2,8-Dibromodibenzo[b,d]furan is playing an increasingly important role. we look forward to future research findings about 10016-52-1.

Reference:
Patent; Changchun Hai Purunsi Technology Co., Ltd.; Zhao Qian; Liu Hui; Han Chunxue; (55 pag.)CN110407829; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 38573-88-5, 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. 38573-88-5, name is 1-Bromo-2,3-difluorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

4.2.1. First-generation strong base process. A mixture of toluene (14.9 L), 2 (3.50 kg, 18.1 mol), 1 (4.92 kg, 14.8 mol), palladium acetate (0.132 kg, 0.588 mol), tri-tert-butylphosphonium tetrafluoroborate (0.174 kg, 0.600 mol), and sodium tert-butoxide (1.88 kg, 19.6 mol) was heated to 95 °C for 4 h. The resulting dark mixture was cooled to 25 °C and diluted with ethyl acetate (44.5 L), washed with saturated ammonium chloride solution (224.7 L), phase split, and concentrated the organic to ~25 L under vacuum. The dark solution was absorbed onto a packed bed of alumina (19.8 kg) and eluted with toluene (203 L). The fractions containing 3 were combined and solvent swapped to IPA and concentration to 3 L/kg of 3. The IPA solution brought to 45 °C and water (1.5 L/kg) was added to the solution over 10 min, and the mixture seeded with 5 wt percent 3. The mixture was cooled to 40 °C over 2.5 h and water (1.5 L/kg) was added to the solution over 50 min. The resulting slurry was cooled to 25 °C over 1 h and aged for an additional 1 h followed by filtration. The cake was washed with a solution of IPA/water (1:1, 9.17 L) and dried under vacuum (at atmospheric pressure, 50 °C) for 24 h to afford 3 (4.15 kg, 63percent, 12:1 dr).

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-2,3-difluorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Desai, Lopa V.; Hay, Michael B.; Leahy, David K.; Wei, Carolyn; Fanfair, Dayne; Rosner, Thorsten; Hsiao, Yi; Tetrahedron; vol. 69; 27-28; (2013); p. 5677 – 5684;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 1347736-74-6,Some common heterocyclic compound, 1347736-74-6, name is 4,7-Dibromo-5-fluoro-2,1,3-benzothiadiazole, molecular formula is C6HBr2FN2S, 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 dried flask was charged with 4,7-Dibromo-5-fluoro-2,1,3-benzothiadiazole (3.0 g, 9.6 mmol), compound 5(3.83 g, 9.58 mmol), Pd2dba3 (0.174 g, 0.19 mml), PPh3 (0.202 g,0.77 mmol) and 100ml of toluene. The reaction mixturewas heatedto 80 C for 48 h. Upon cooling, 30 mL of 2 M HCl was added andthen stirred for 1 h. After extract with dichloromethane, the solventwas removed by vacuum evaporation, and then recrystallized withchloroform/methanol and filtered. The solid was washed withcopious methanol, and dried under vacuum for 24 h. Compound 6was a red solid.Yield: 40.9% (1.67 g). 1H NMR (CDCl3, 500 MHz, [ppm]): delta 9.904(s, 1H), 8.066 (d, 1H, J 4 Hz), 7.764 (m, 2H), 7.458 (d, 1H, J 4 Hz),7.392 (d, 1H, J 4 Hz); APCI: m/z 425.0, calcd 423.88.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4,7-Dibromo-5-fluoro-2,1,3-benzothiadiazole, its application will become more common.

Reference:
Article; Lim, Bogyu; Sun, Huabin; Noh, Yong-Young; Dyes and Pigments; vol. 146; (2017); p. 520 – 528;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 2695-48-9,Some common heterocyclic compound, 2695-48-9, name is 8-Bromo-1-octene, molecular formula is C8H15Br, 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: The alkyl bromide (1.0 equiv) was added to a solution of mercaptoaceticacid (1.0 equiv) in methanol (10.0 mL) and the resultingsolution stirred. Then a solution of NaOH (2.0 equiv) in methanol(5.0 mL)was added slowly, and the final mixturewas stirred at roomtemperature or heated to reflux until absence of the alkyl bromide(checked by TLC). The reaction mixture was concentrated in vacuo,diluted with H2O, and neutralized with 1 N HCl. Then the obtainedreaction mixture was extracted with EtOAc. The combined organicfractions were washed with brine, dried with Na2SO4, and concentratedin vacuo. Purification of the crude residue by column chromatography(petroleum ether/EtOAc) afforded the title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 8-Bromo-1-octene, its application will become more common.

Reference:
Article; Chen, Ying; Wu, Bolin; Hao, Yameng; Liu, Yunqi; Zhang, Zhili; Tian, Chao; Ning, Xianling; Guo, Ying; Liu, Junyi; Wang, Xiaowei; European Journal of Medicinal Chemistry; vol. 171; (2019); p. 420 – 433;,
Bromide – Wikipedia,
bromide – Wiktionary

59907-13-0, name is 2-Bromo-1-fluoro-3-methylbenzene, belongs to bromides-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. HPLC of Formula: C7H6BrF

General procedure: To a mixture of the appropriate amine E (1 eq), the appropriate halide (1.05 to 1.2 eq) and sodium ferf-butoxide (2 eq) in toluene (3 mL/mmol) under N , was added BINAP (0.2 eq) and Pd2(dba)3 (0.1 eq). The rxn mixture was flushed with N , heated to a given temperature in a sealed vial and stirred for a given time (see Table 27). It was partitioned between water and EtOAc and the org. phase was washed with brine, dried over MgSCh and concentrated in vacuo. The crude was purified by CC using Hept/EtOAc.

The synthetic route of 59907-13-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IDORSIA PHARMACEUTICALS LTD; FROIDEVAUX, Sylvie; HUBLER, Francis; MURPHY, Mark; RENNEBERG, Dorte; STAMM, Simon; (266 pag.)WO2019/137927; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 399-94-0,Some common heterocyclic compound, 399-94-0, name is 1-Bromo-2,5-difluorobenzene, molecular formula is C6H3BrF2, 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 2-bromo-1,4-difluorobenzene (186 g) in THF (1.0 L) was added 2.0M isopropylmagnesium chloride solution in THF (482 mL) at -40C, and continuously stirred at 5C for 1 h. To the above reaction mixture was added a solution of tert-butyl 2-oxopyrrolidine-1-carboxylate (215.5 g) in THF (250 mL) dropwise, and continuously stirred at 10C for 2h. The reaction mixture was quenched with a saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure to afford a crude product of the title compound (323.4 g), which was used in a next step without purification.

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-2,5-difluorobenzene, its application will become more common.

Reference:
Patent; Chia Tai Tianqing Pharmaceutical Group Co., Ltd.; Centaurus BioPharma Co., Ltd.; Lianyungang Runzhong Pharmaceutical Co., Ltd.; ZHU, Li; HU, Yuandong; WU, Wei; DAI, Liguang; DUAN, Xiaowei; YANG, Yanqing; SUN, Yinghui; HAN, Yongxin; PENG, Yong; KONG, Fansheng; LUO, Hong; YANG, Ling; XU, Hongjiang; GUO, Meng; ZHONG, Zhaobai; WANG, Shanchun; (80 pag.)EP3533796; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary