Tag: M.W=100-200

Electric Literature of 53078-85-6,Some common heterocyclic compound, 53078-85-6, name is 2-Bromo-5-methylaniline, molecular formula is C7H8BrN, 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 5.0 g of 2-bromo-5-methylaniline in 17 ml of hydrochloric acid (37%) was added dropwise, at 0 C. within 30 minutes, a solution of 1.9 g of sodium nitrite in 9.6 ml of water. Subsequently, at 0 C., a solution of 16.6 g of tin chloride in 15 ml of hydrochloric acid (37%) was added dropwise, and the mixture was stirred at this temperature for a further 1.5 hours. After adding 60 ml of sodium hydroxide solution (50%) and 30 ml of ice-water (pH>10), the mixture was extracted three times with 500 ml each time of ether. The combined organic phases were washed with semisaturated sodium chloride solution and dried over sodium sulphate. The filtrate was acidified with 4.0M hydrochloric acid in 1,4-dioxane solution and the resulting precipitate was then filtered off and dried. Yield: 5.85 g of the title compound.NMR (300 MHz, DMSO-d6): delta=2.22 (3H), 6.70 (1H), 6.93 (1H), 7.39 (1H), 7.78 (1H), 10.29 (2H).

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-5-methylaniline, its application will become more common.

Reference:
Patent; Bayer Schering Pharma AG; US2010/29598; (2010); A1;,
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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;,
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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;,
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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;,
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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;,
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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;,
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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;,
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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. 108-85-0, name is Bromocyclohexane, A new synthetic method of this compound is introduced below., Formula: C6H11Br

General procedure: A mixture of organic halide or epoxide (1.0 mmol), sodium azide(1.2 mmol), and alkyne (1.0 mmol) was stirred in water (3.0 mL) assolvent. Then, Cu(Bb)(PCy3) (5 mg) was added to the reaction mixtureand it was further stirred at 60 C for a period of time. After completionof the reaction (monitored by TLC), the reaction mixture was extractedby ethyl acetate (5 mL, 3 times) and dried over anhydrous Na2SO4 andthe procedure was followed by concentration under reduced pressure.The crude products were purified by column chromatography on silicagel (silica gel, n-hexane-EtOAc) to give the pure products.

The synthetic route of 108-85-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Khalili, Dariush; Evazi, Roya; Neshat, Abdollah; Aboonajmi, Jasem; Osanlou, Farzane; Inorganica Chimica Acta; vol. 506; (2020);,
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Related Products of 51376-06-8,Some common heterocyclic compound, 51376-06-8, name is 5-Bromobenzo[c][1,2,5]oxadiazole, molecular formula is C6H3BrN2O, 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.

5-bromo-2,1,3-benzoxadiazole (0.17 g) (which can be prepared according to Org. Proc. Res. Dev., (2003), 7, 436-445 at page 437), triethylamine (0.11 g) and dichlorobistriphenyl-phosphine palladium (II) (0.12 g) were added to a solution of N- ({(5S)-3-[3-fluoro-4-(trimethylstannyl)phenyl]-2-oxo-1,3-oxazolidin-5- yl}methyl)acetamide (0.18 g) (which can be prepared according to Example 8 of WO 01/94342, page 52) in dry dimethyl formamide (15 mL) and the reaction mixture was heated at 100 C for about 3 hours, cooled and diluted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and concentrated. The crude product was purified by column chromatography using 2 % methanol in dichloromethane as eluent to yield the title compound (0.14 g). Melting point: 156-165 C; EMS (m/z): 388 (M+H); 1HNMR(CDCB): delta 7.91 (m, 2H), 7.62 (m, 2H), 7.52 (t, 1H), 7.35 (dd, 1H), 6.10 (t, 1H), 4.84 (m, 1H), 4.12 (t, 1H), 3.87 (t, 1H), 3.71 (m,2H), 2.02 (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 5-Bromobenzo[c][1,2,5]oxadiazole, its application will become more common.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; WO2006/35283; (2006); A1;,
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Related Products of 10485-09-3, The chemical industry reduces the impact on the environment during synthesis 10485-09-3, name is 2-Bromoindene, I believe this compound will play a more active role in future production and life.

A solution of (pS)-9 (2.00g, 4.04mmol) in THF (70mL) was cooled to -78C, treated with nBuLi (1.6M in hexanes, 3.03mL, 4.85mmol) and stirred at -78C for 30min. A solution of ZnCl2 (0.5M in THF, 9.70mL, 4.85mmol) was added dropwise, the solution warmed to rt over 30min and stirred at rt for 1h. Next, Pd(PPh3)2Cl2 (0.140g, 0.200mmol) in THF (5mL) was treated with DIBAL (1M in THF, 0.400mL, 0.440mmol), stirred for 5min and added dropwise via cannula to the reaction. The resultant solution was heated at reflux and a solution of 2-bromoindene42 (1.56g, 8.08mmol) in THF (5mL) added dropwise over 30min. After refluxing for 4d the solution was cooled to rt, quenched with NH4Cl(aq) (10mL), washed with water (2×40mL), brine (40mL), dried over MgSO4 and concentrated in vacuo. Purification was achieved using flash column chromatography (pet. ether) to give the title compound as an orange oil (1.47g, 75%). Rf=0.31 (pet. ether); [alpha]25D=+235.3[alpha]D25=+235.3 (c 1.02, CHCl3); IR numax 2943, 2866, 1461, 1391, 1130, 1105, 1057, 999, 908, 882cm-1; 1H NMR (400MHz) delta 1.18-1.70 (21H, m, Si(iPr)3), 3.72 (1H, d, J=22.8, IndCH2), 3.79 (1H, d, J=22.8, IndCH2), 4.07 (5H, s, Cpunsub), 4.26 (1H, app t, J=2.5, Cpsub), 4.42 (1H, dd, J=2.5, 1.5, Cpsub), 4.48 (1H, dd, J=2.5, 1.5, Cpsub), 4.74 (1H, d, J=11.6, CpCH2), 4.95 (1H, d, J=11.6, CpCH2), 7.08 (1H, s, IndCH), 7.16 (1H, app dt, J=7.2, 0.8, ArH), 7.25 (1H, app t, J=7.2, ArH), 7.31 (1H, d, J=7.2, ArH), 7.45 (1H, d, J=7.2, ArH); 13C NMR (100MHz) delta 12.2 (CH), 18.2 (CH3), 41.0 (CH2), 61.4 (CH2), 67.3 (CH), 69.0 (CH), 69.7 (CH), 70.9 (CH), 81.4 (C), 85.0 (C), 120.1 (CH), 123.4 (CH), 123.8 (CH), 126.4 (CH), 126.6 (CH), 142.7 (C), 145.5 (C), 146.2 (C); m/z (EI+) 510 (10%, M++HNa), 509 (26%, M++Na), 314 (23%, M++H-OTIPS), 313 (100%, M+-OTIPS), 301 (15%, M+-COTIPS), 269 (7%); HRMS C29H38FeNaOSi calcd 509.1934, found 509.1903; Anal. Calcd for C29H38FeOSi: C, 71.59; H, 7.87. Found: C, 71.10; H, 7.81.

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-Bromoindene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Anderson, James C.; Grounds, Helen; Szaloki, Gyoergy; Tetrahedron Asymmetry; vol. 24; 17; (2013); p. 1023 – 1034;,
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