Tag: M.W=200-300

Application of 314084-61-2, A common heterocyclic compound, 314084-61-2, name is 2-Bromo-1,3-diethyl-5-methylbenzene, molecular formula is C11H15Br, 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.

Dihydro-1H-pyrazolo[1,2-d][1,4,5]oxadiazepine-7,9(2H,8H)-dione (3.4 g, 20 mmol) at 20 C Soluble in 40mL dimethylformamide,And added 2,6-diethyl-4-methylbromobenzene (4.09 g, 18 mmol) andPd(PPh3)2Cl2 (1.26 g, 1.8 mmol) was then stirred at 135 C for 6 hours. After cooling the above reaction system to room temperature, 200 mL of ethyl acetate and 200 mL of diethyl ether were added, and the reaction mixture was poured into a suction filter.100 mL of water and 100 mL of dichloromethane were added to the filtered residue.Acidified with hydrochloric acid. The organic phase was separated, dried and concentrated by evaporation.The residue was chromatographed on silica gel column (ethyl acetate / petroleum ether = 2:1 (V/V))8-(2,6-Diethyl-4-methylphenyl)tetrahydropyrazolo[1,2-d][1,4,5]oxazepine-7,9(2H,8H) -dione4.72 g, yield 82.9%.

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; Lanzhou Fine Chemical High Technology Development Corporation; Gansu Chemical Institute Co., Ltd.; Liu Rong; Wang Xiaoxia; Ji Pengyan; Wei Wanlei; He Kaiyu; Liu Yunli; (9 pag.)CN108864144; (2018); A;,
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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. 54962-75-3, name is 3-Bromo-5-(trifluoromethyl)aniline, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 3-Bromo-5-(trifluoromethyl)aniline

To a mixture of 3-amino-5-bromobenzotrifluoride (1.0 g, 4.17 mmol) in pyridine (10 mL) at 0- 5C was added dropwise methanesulfonyl chloride (0.389 mL, 5 mmol). The reaction mixture was stirred at rt for 4 days. As the reaction was not completed, the reaction mixture was then heated in a microwave oven at 150C for 15 min. There was no evolution, so the reaction was stopped. The reaction mixture was concentrated until dryness, and the residue was co- evaporated with toluene. The residue was then diluted with a saturated aqueous solution of NaHC03 and extracted with DCM. The organic layer was dried over MgS04 and evaporated. Purification by Flash chromatography using CombiFlash Companion ISCO system (Redisep silica 12g column, eluting with Cyclohexane/EtOAc 100:0 to 70:30) gave the title compound (1.05 g, 79% yield) as a white solid. 1H-NMR (400 MHz, DMSO-d6, 298 K): ? ppm 3.14 (s, 3H) 7.48 (s, 11-1) 7.64 (s, 11-1) 7.68 (s, 1 H) 10.42 (s, 1 H). MS(10): 316.3-318.2 [M-1]

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 54962-75-3.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; HEBACH, Christina; HOeGENAUER, Klemens; HOLLINGWORTH, Gregory; LEWIS, Ian; SMITH, Alexander, Baxter; SOLDERMANN, Nicolas; STAUFFER, Frederic; WOLF, Romain; ZECRI, Frederic; WO2013/57711; (2013); A1;,
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Related Products of 142808-15-9, 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. 142808-15-9, name is 4-Bromo-2-fluorobenzotrifluoride belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[00199] step 2: (R)-tert-butyl 2-(3 -fluoro-4-(trifluoromethyl)benzoyl)pyrrolidine- 1 -carboxylate. To a stirred solution of 4-bromo-2-fluoro-l-(trifluoromethyl)benzene (4.854 g, 19.98 mmol) and ether (50 mL) cooled to -78 C under nitrogen was added w-butyl lithium (7.99 mL, 19.98 mmol) slowly over 10 min. The reaction was transferred via cannula to a solution of 42b (4.30 g, 16.65 mmol) in THF (50 mL) cooled to -78 C. The reaction was stirred for 10 min after all aryl lithium was added. The reaction was quenched with water and extracted with DCM. The organic layer was dried (MgS04), concentrated and the crude product purified by Si02 chromatography eluting with an EtOAc/hexane gradient (1 to 5% EtOAc). A close running impurity was not removed by this purification. The compound was further purified on a SP4 reverse phase column chromatography eluting with MeCN/water gradient (65 to 100% MeCN) to afford 2.105 g (33.2%) of 44.

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

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; BLAKE, James, F.; CHEN, Huifen; CHICARELLI, Mark, Joseph; DEMEESE, Jason; GARREY, Rustam, Ferdinand; GAUDINO, John; GAZZARD, Lewis; KAUS, Robert J.; KINTZ, Samuel; MOHR, Peter J.; MORENO, David, A.; SCHWARZ, Jacob; SIEDEM, Christopher, S.; WALLACE, Eli, M.; WO2013/20062; (2013); 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. 615-55-4, name is 3,4-Dibromoaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C6H5Br2N

EXAMPLE 20 4-[(3,4-Dibromophenyl)amino]-6-nitro-3-quinolinecarbonitrile A mixture of 6.20 g (26.6 mmol)of 4-chloro-6-nitro-3-quinolinecarbonitrile and 8.00 g (31.9 mmol) of 3,4-dibromoaniline in 160 mL of ethanol was refluxed under N2 for 5 h. Saturated sodium bicarbonate was added and volatile material was removed. The residue was slurried with hexane, collected, washed with hexane and water and dried. The insoluble material was repeatedly extracted with boiling ethyl acetate and the solution was then filtered through silica gel. The solvent was removed to give 3.80 g of green solid: mass spectrum (electrospray, m/e): M+H 449.

The synthetic route of 615-55-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Cyanamid Company; US6002008; (1999); A;; ; Patent; American Cyanamid Company; US6384051; (2002); B1;,
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Reference of 15155-41-6, A common heterocyclic compound, 15155-41-6, name is 4,7-Dibromo-2,1,3-benzothiadiazole, molecular formula is C6H2Br2N2S, 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.

In two 250mL flask, followed by adding ethanol 150ml, 2,5- dibromo benzothiadiazole (5. 88g, 20mmol), the flask was placed in an ice-water bath, sodium borohydride was slowly added repeatedly (1. 52g, 40mmol after), 0 C reaction lOmin, room temperature, the reaction 3h, the reaction was completed. After rotary evaporation to dryness in vacuo purified by column chromatography, petroleum ether: dichloromethane = 1: 1 to giveOff-white product 5. 05g (95% yield).

The synthetic route of 15155-41-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NanjingFriend Photoelectric Technology Co., Ltd; MENG, HONG; ZHANG, XIAOTAO; YUAN, XIAO; YAN, LIJIA; (10 pag.)CN103450226; (2016); B;,
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Some common heterocyclic compound, 156682-52-9, name is 1,4-Dibromo-2,3-difluorobenzene, molecular formula is C6H2Br2F2, 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. HPLC of Formula: C6H2Br2F2

Preparation of iso-PrMgCl-LiCl-A sample of LiCl (4.56 g, 107.6 mmol) was dried under high vacuum with a heat gun for 10 min. To the dry solid under a N2 atmosphere at 23 C. was added iso-PrMgCl (53.8 mL, 107.6 mmol, 2M solution in THF) and the resulting mixture was stirred at 23 C. for 3 days.To a solution of D-1c (1.29 mL, 10 mmol) in THF (5 mL) at 40 C. was added the iso-PrMgCl-LiCl solution (5.5 mL, 11 mmol, 2.0M in THF) at a rate that maintained the reaction temperature below -30 C. Stirring was continued at -35 to -30 C. for 1 h then warmed to -7 C. for an additional 1 h. The reaction mixture was cooled to -30 C. and DMF (1.00 mL, 13 mmol) was added in one portion (temperature rose to -23 C.) and stirring continued for 3.5 h at -25 to +15 C. The reaction mixture was poured into 1M H2SO4 and ice and the resulting mixture was saturated with solid NaCl and twice extracted with MTBE. The combined extracts were dried (MgSO4), filtered and concentrated in vacuo to afford 2.17 g (98%) of D-1d as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 156682-52-9, its application will become more common.

Reference:
Patent; Roche Palo Alto LLC; US2008/249151; (2008); 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. 699-03-6, name is 1-(4-Bromophenyl)-N-methylmethanamine, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-(4-Bromophenyl)-N-methylmethanamine

A mixture of l-(4-bromophenyl)-N-methylmethanamine (14.0 g, 70.0 mmol), 2-(but- 3-yn-l-yl)isoindoline-l,3-dione (16.5 g, 83.0 mmol), Cul (3.33 g, 17.5 mmol) and CS2CO3 (114 g, 351 mmol) in deoxygenated dioxane (280 mL) was further deoxygenated by bubbling nitrogen gas for 1.25 h. through the mixture. PdCl2([l,r-bis(diphenylphosphino)ferrocene]) (5.71 g, 7.00 mmol) was added and the mixture further deoxygenated with nitrogen for 1 h before heating to 80C for 18 h under an atm. of N2. The reaction was allowed to cool to room temperature and filtered through celite with EtOAc. The organic mother liquor was washed with 1 molar NaOH, water, brine, dried with Na2S04, filtered and concentrated in vacuo. The residue was chromatographed on silica gel (330 g Isco column, 1 to 10% MeOH in DCM with 1% N Eh in the eluents over 36 min.) to give 23.3 g of 2-(4-(4- ((methylamino)methyl)phenyl)but-3- yn-l-yl)isoindoline-l,3-dione as a black oil that was 86% 74 by weight. The raw product was used as is in the next reaction. 1H NMR (400MHz, chloroform-d) d = 7.87 (dd, =3.0, 5.5 Hz, 2H), 7.73 (dd, J=3. l, 5.4 Hz, 2H), 7.31 – 7.28 (m, 2H), 7.23 – 7.19 (m, 2H), 3.97 (t, J=1 A Hz, 2H), 2.83 (t, J=1 A Hz, 2H), 2.43 (s, 3H), 1.19 (t, J=12 Hz, 2H). LC/MS RT = 0.49 min., 319.0 [M+H]+

The synthetic route of 699-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ADVITECH ADVISORY AND TECHNOLOGIES SA; BECK, Brent Christopher; PERALES, Joe B.; SPEAKE, Jason D.; FERRANDO, Ilaria; (28 pag.)WO2019/115000; (2019); A1;,
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Some common heterocyclic compound, 16518-62-0, name is 3-Bromo-N,N-dimethylaniline, molecular formula is C8H10BrN, 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. Computed Properties of C8H10BrN

It was prepared as outlined in Scheme 1 In an oven-dried 50 mL round bottom flask under an atmosphere of anhydrous argon, THF (10 mL) was added followed by 3-bromo-N,N-dimethylaniline (5.00 mmol, 1.00 g). This clear, colourless solution was cooled to -90 °C using a Juablo cooler with a cold finger and an isopropanol bath in an appropriate sized Dewar. The aniline reagent solution was stirred at this temperature for 15 min to ensure the solution was sufficiently cold. Butyl lithium (3.44 mL, 1.60 M in hexanes) was added dropwise at -90 °C over 20 min. The resulting clear light yellow solution was stirred for 15 min at -90 °C. To this 3-lithium N,N-dimethylaniline intermediate was added N-methoxy-N-methyl-2,2,2-trifluoroacetamide (5.50 mmol, 0.857 g) dissolved in anhydrous THF (4 mL), dropwise over 15 min. The resulting solution was stirred at -90 °C for 30 min then warmed to room temperature by removing the reaction flask from the cooling bath. The resulting reaction mixture was stirred for 16 h at room temperature then extracted with 1 M HCl (3 * 10 mL). The combined aqueous layers were added to a separatory funnel and solid NaHCO3 was added until the solution stopped bubbling. During this addition a yellow liquid formed on the top of the aqueous layer. The aqueous layer was extracted with diethyl ether (3 * 15 mL). The combined organic layers were dried over Na2SO4, gravity filtered and concentrated in vacuo. The crude viscous yellow liquid was purified by flash chromatography on silica gel (5percent ethyl acetate/94percent hexanes/1percent triethylamine, Rf: 0.38) to afford the desired product as a clear yellow liquid (0.854 g, 79percent): 1HNMR (CDCl3): d 3.02 (s, 6H), 7.02?7.05 (m, 1H), 7.36?7.38 (m,3H) (Supplementary Fig. S1). 13C NMR (CDCl3): d 40.0, 112.3,116.8 (q, JC,F = 298.2 Hz), 117.9, 119.1, 129.5, 130.4, 150.5, 181.0(q, JC,F = 34.3 Hz) (Supplementary Fig. S2). IR (Neat): 2898 (m),2814 (w), 1709 (s), 1600 (s), 1573 (s), 1503 (s), 1437 (m), 1363(m), 1105 (s), 1007 (s) cm1 (Supplementary Fig. S3). LRMS m/z: 218 (M+1, 11), 217 (M+, 100), 216 (74), 148 (24), 120 (24), 119(13), 118 (10), 104 (10), 77 (11), 74 (13) (Supplementary Fig. S4). HRMS (ESI): MH+ found 218.0786, calculated for C10H11F3-NO+ = 218.0787(Supplementary Fig. S5). HPLC: retention time 2.59 min; purity 96.1percent (Supplementary Fig. S6).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 16518-62-0, its application will become more common.

Reference:
Article; Jollymore-Hughes, Courtney T.; Pottie, Ian R.; Martin, Earl; Rosenberry, Terrone L.; Darvesh, Sultan; Bioorganic and Medicinal Chemistry; vol. 24; 21; (2016); p. 5270 – 5279;,
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Related Products of 29086-41-7,Some common heterocyclic compound, 29086-41-7, name is 1,1-Bis(bromomethyl)cyclopropane, molecular formula is C5H8Br2, 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 1 .78 g (4.80 mmol) of compound 2-1 and 2.2 g (9.7 mmol) of 1 ,1 -bis(bromomethyl)cyclopropane in 20 mL of DMSO was added 3.2 g (9.7 mmol) of CS2CO3. The mixture was stirred at rt for 3 h under argon atmosphere, then diluted with 50 mL of water and extracted with four 100 mL portions of ethyl acetate. The combined organic layers were washed with brine and dried over anhydrous Na2S04. After filtration, the filtrate was concentrated under reduced pressure to afford a residue, which was purified by silica gel column chromatography eluting with 0 to 15 % gradient of EtOAc in PE to afford compound 6-1. LC-MS: m/e = 324 [M+H]+.

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

Reference:
Patent; ANGEX PHARMACEUTICAL, INC.; WU, Wen-Lian; YANG, Zhiqiang; LEE, Francis; TAN, John Qiang; (112 pag.)WO2019/94143; (2019); A1;,
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22385-77-9, name is 1-Bromo-3,5-di-tert-butylbenzene, 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. COA of Formula: C14H21Br

Bromo-3,5-di-tert-butylbenzene (1.3 g, 5 mmole) was dissolved in THF (20 mL), to this solution was slowly added n-BuLi (1.6 M, 3.3 mL) at -78° C., the reaction was stirred at this temperature for 30 min, trimethyl borate (0.75 g, 7.5 mmole) was added all at once, stir over night while the reaction was allowed to slowly warm up to room temperature. Hydrochloric acid (6N, 5 mL) was added and stirred for 3 hrs at room temperature. Water (200 mL) was added, and the precipitate was collected, washed with water (10 mL.x.3), dried under vacuum to give titled compound.

The synthetic route of 22385-77-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Adams, Alan D.; Santini, Conrad; US2009/30012; (2009); A1;,
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