Tag: M.W=100-200

A common heterocyclic compound, 55289-36-6, name is 3-Bromo-2-methylaniline, molecular formula is C7H8BrN, 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. 55289-36-6.

Example lOld Methyl 3-((3-Bromo-2-methylphenylamino)methyl)-5-ieri- xylate lOldA 250-mL single-necked round-bottomed flask equipped with a magnetic stirrer was purged with nitrogen and charged with 101c (1.09 g, 4.68 mmol), 3-bromo-2-methyl-aniline (2.61 g, 14.0 mmol) and acetonitrile (25 mL). Cesium carbonate (1.67 g, 5.15 mmol) was added and the mixture was stirred at room temperature for 16 h. The reaction mixture was then concentrated under reduced pressure. Purification of the resulting residue by column chromatography afforded a 70% yield (1.30 g) of lOld as a yellow oil: ]H NMR (300 MHz, CDCI3) delta 6.92 (m, 2H), 6.85 (s, 1H), 6.57 (dd, 1H, / = 4.8, 2.1 Hz), 4.60 (s, 2H), 3.86 (s, 3H), 2.29 (s, 3H), 1.37 (s, 9H); MS (ESI+) mJz 396.2 (M+H).

The synthetic route of 3-Bromo-2-methylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD CONNECTICUT, INC.; GENENTECH, INC.; CURRIE, Kevin S.; WANG, Xiaojing; YOUNG, Wendy, B.; WO2012/30990; (2012); 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. 1073-39-8, name is 3-Bromobicyclo[4.2.0]octa-1,3,5-triene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 1073-39-8

To a mixture of 3-bromobicyclo[4.2.0]octa-1,3,5-triene (80 g, 437.05 mmol, 1.05 equiv) in THF (800 mL) was added n-BuLi (2.5M in hexane, 180 mL, 1.10 equiv) dropwise at -78C, and the reaction mixture was stirred at – 78C for 30 min. 5-Bromo-2-methoxybenzaldehyde (89.5 g, 416.19 mmol, 1.00 equiv) in THF (800 mL) was then added to the solution dropwise at -78C. The reaction mixture was stirred at -78C for 2 h. NH4CI/H20 was added and the mixture was extracted with EtOAc thrice. The combined extracts were washed with brine and dried over Na2S04, then concentrated and purified by chromatography on silica gel (10: 1 PE/EA) to yield (5-bromo-2- methoxyphenyl)(1,2-dihydrocyclobutabenzen-4-yl)methanol as a colorless oil.

The synthetic route of 1073-39-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; GAUL, Micheal; KUO, Gee-Hong; XU, Guozhang; LIANG, Yin; (218 pag.)WO2018/89449; (2018); A1;,
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2270-59-9, name is 5-Bromo-2-methylpent-2-ene, 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. 2270-59-9

A dry Schlenk tube equipped with a stirring bar was charged with dimethyl oxalate(0.5 g, 4.2 mmol, 1.0 equiv.) and then the flask was evacuated and refilled with N2 (x3). Dry THF (0.7 M) was added and the mixture was cooled to -78 C. A freshlyprepared solution of 4-methylpent-3-en-1-yl)magnesium bromide (1.05 equiv.) wasadded by dropwise [Grignard preparation: a dry Schlenck tube equipped with astirring bar was charged with Mg turnings (1.1 equiv.) and then the flask wasevacuated and refilled with N2 (x 3). The minimum amount of THF was added andthen 5-bromo-2-methylpent-2-ene (0.3 equiv.) was added neat. Once the Grignardreaction started the remaining 5-bromo-2-methylpent-2-ene (0.75 equiv.) were addedas a solution in THF (2 M). The corresponding mixture was stirred for 1 additional hour]. The mixture was allowed to warm to room temperature overnight. NH4Cl was added and the mixture was diluted with Et2O. The layers were separated and the organic layer was dried (MgSO4), filtered and evaporated. Purification by columnchromatography on silica gel, eluting with petrol-Et2O 95:5, gave S7 (0.2 g, 25%) asan oil. 1H NMR (400 MHz, CDCl3) delta 5.07 (1H, t, J = 7.2 Hz), 3.86 (3H, s), 2.87 (2H,t, J = 7.3 Hz), 2.32 (2H, q, J = 7.3 Hz), 1.67 (3H, s), 1.62 (3H, s); 13C NMR (101 MHz, CDCl3) delta 194.1, 161.6, 133.7, 121.9, 53.0, 39.7, 25.8, 21.9, 17.8; HRMS (ESI): Found MNH4+ 188.1280 C9H18O3N requires 188.1281.

Statistics shows that 2270-59-9 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2-methylpent-2-ene.

Reference:
Article; Davies, Jacob; Angelini, Lucrezia; Alkhalifah, Mohammed A.; Sanz, Laia Malet; Sheikh, Nadeem S.; Leonori, Daniele; Synthesis; vol. 50; 4; (2018); p. 821 – 830;,
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A common heterocyclic compound, 553-94-6, name is 2,5-Dimethylbromobenzene, molecular formula is C8H9Br, 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. 553-94-6.

1) Add 1 mol of 2-bromo-p-xylene or chloroacetyl chloride to the reaction kettle.The catalyst and DMSO were heated to 100 C under stirring for 5 h.Then a mixture of sodium sulfite and water was added dropwise to control the dropping time to 45 min.After the completion of the dropwise addition, the reaction temperature was raised to 135 C, and the reaction was continued for 7.5 h; The ratio of 2-bromo-p-xylene to chloroacetyl chloride is 1:1.14,The ratio of 2-bromo-p-xylene to catalyst is 1:0.07, and the ratio of 2-bromo-p-xylene to DMSO is 1g: 13ml.The ratio of 2-bromo-p-xylene to sodium sulfite was 1:1.18, and the ratio of sodium sulfite to water was 1:4.5. The preparation process of the catalyst is: Mix ruthenium oxide and 10% palladium carbon in a weight ratio of 1:20. Then soaked in 4% concentration of hydrochloric acid for 6 minutes,Then, a solid was obtained by filtration, and the solid was washed and then placed at 280 C for 2.5 h to obtain a catalyst. 2) cooling the system, filtering to remove insoluble matter to obtain a filtrate, and adding the filtrate to about 5 volumes of water.Then, the filtrate is added twice the volume of toluene, and the layer is allowed to stand, and the organic phase is washed with water.After drying with anhydrous sodium sulfate,Concentration gave the product in a molar yield of 98.1% and a HPLC purity of 97.5%.

The synthetic route of 2,5-Dimethylbromobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong Nong Pharmaceutical Xue Institute; Jinan Kehai Co., Ltd.; Fu Hongxin; Yang Chaohui; Wang Ling; (6 pag.)CN109369378; (2019); 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. 3814-30-0, name is (Bromomethyl)cyclopentane, This compound has unique chemical properties. The synthetic route is as follows., 3814-30-0

EXAMPLE 65 1-Cyclopentylmethyl-3-methyl-6-(4-pyridyl)pyrazolo[3,4-d]pyrimidin-4-amine To a solution of 3-methyl-6-(4-pyridyl)-pyrazolo[3,4-d]pyrimidin-4-amine (6.0 g, 0.027 mol) in DMF (50 ml) at 0 C. was added 60% NaH/mineral oil dispersion (1.06 g, 0.027 mol) in one portion. The reaction mixture was warmed to room temperature and stirred for 1 hour. The reaction mixture was cooled to 0 C. and cyclopentylmethyl bromide (4.3 g, 0.027 mol) was added dropwise over 5 minutes. The reaction mixture was warmed to room temperature and stirred for 50 hours. The solvent was removed in vacuo, the yellow slurry was added to water (100 ml) and acidified with acetic acid. The resulting paste was stripped to dryness and the residue was slurried with ethanol. A tan solid was collected by filtration and purified by column chromatography on silica eluding with ether/ethanol/water (97.5/2/0.5) followed by recrystallization from cyclohexane to afford 2.2 g (26%) of 1-cyclopentylmethyl-3-methyl-6-(4-pyridyl)-pyrazolo[3,4-d] -pyrimidin-4-amine, m.p. 177-178 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; Sterling Winthrop Inc.; US5294612; (1994); A;,
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A common heterocyclic compound, 1647-26-3, name is 1-Bromo-2-cyclohexylethane, molecular formula is C8H15Br, 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. 1647-26-3.

60% sodium hydride (526 mg, 0.013 mol) were added portion wise to a mixture of isatin (1.75 g, 0.012 mol) dissolved in 35 mL of dimethylformamide. The reaction medium was stirred at room temperature for 2 hours. A solution of l-Bromo-2- cyclohexylethane (2.5 g, 0.013 mol) dissolved in dimethylformamide (3 mL) was then added drop wise. The reaction medium was stirred at room temperature overnight. After extraction with ethyl acetate, the organic layer was washed with hydrochloric acid (0.4 N) and water. The organic fraction was dried over MgSO4 and concentrated under vacuum. The title compound was prepared as an orange solid following Method A. The resulting solid was washed with a mixture of heptane/AcOEt. Yield: 100%. 1H NMR (CDCl3): delta 0.92-1.05 (m, 2H), 1.12-1.41 (m, 4H), 1.57 (q, J = 6.9Hz, 2H), 1.63-1.82 (m, 5H), 3.74 (t, J = 7.6 Hz, 2H), 6.88 (d, J = 7.8 Hz, IH), 7.11 (t, J = 7.5 Hz, IH), 7.56 – 7.61 (m, 2H). 13C NMR (CDCl3): delta 26.09 (CH2), 26.4 (CH2), 33.08 (CH2), 34.42 (CH2), 35.42 (CH), 38.21 (CH2), 110.12 (CH), 117.66 (C), 123.57 (CH), 125.41 (CH), 138.3 (CH), 151.01 (C), 158.03 (C=O). 178.71 (C=O).

The synthetic route of 1-Bromo-2-cyclohexylethane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; WO2009/12227; (2009); 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. 3814-30-0, name is (Bromomethyl)cyclopentane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 3814-30-0

To a solution of 3-cyclopropylimidazo[1 ,5-a]pyrazin-8(7H)-one (300 mg, 1.71 mmol) in anhydrous DMF (5 mL) was added K2CO3 (355 mg, 2.57 mmol) and (bromomethyl)cyclopentane (335 mg, 2.05 mmol). The reaction was stirred at 65C for 16 hours. The mixture was filtered and the filtrate was purified by preparative LC- MS to yield 7-(cyclopentylmethyl)-3-cyclopropylimidazo[1 ,5-a]pyrazin-8(7/-/)-one 210 mg (47%). NMR (DMSO-ds, 400 MHz): delta 7.53 (s, 1 H), 7.51 (d, J = 6.0 Hz, 1 H), 6.90 (d, J = 6.0 Hz, 1 H), 3.69 (d, J = 7.6 Hz, 2H), 2.29-2.24 (m, 2H), 1.58-1.45 (m, 6H), 1.22-1.19 (m, 2H), 1.00- 0.89 (m, 4H). LC-MS: (m/z) 258.2 (MH+) tR (minutes, method 3) = 2.24 minutes

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

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; (157 pag.)WO2018/78038; (2018); A1;,
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A common heterocyclic compound, 766-81-4, name is 3-Bromophenylacetylene, molecular formula is C8H5Br, 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. 766-81-4.

In a 100 mL roundbottom flask, LiHMDS (1.0 M in THF, 3.0 mL, 3.0 mmol, 1.1 equiv) was dissolved in 22 mL anhyd hexanes and cooled to 0 C. 1-bromo-3- ethynylbenzene (415 muL, 3.3 mmol, 1.2 equiv) was added and the reaction removed from the cold bath and stirred for 15 min. The reaction was recooled to 0 C, and (R,E)-N-(3-((tert- butyldiphenylsilyl)oxy)propylidene)-2-methylpropane-2-sulfinamide (1.15 g, 2.77 mmol, 1.0 equiv) was transferred via cannula into the reaction in 5.5 mL anhyd hexanes. The reaction was allowed to warm to room temperature with stirring for 12 h. Equal volumes of saturated aqueous NH4Cl and Et2O (20 mL each) were added to the reaction mixture. The layers were separated and the aq layer extracted with Et2O (3 ¡Á 20 mL) then EtOAc (1 ¡Á 20 mL). The combined organic extracts were washed with brine (1 ¡Á 20 mL), dried (Na2SO4), filtered, and concentrated by rotary evaporation. 1H NMR analysis of the crude sample indicated the product was produced in >20:1 d.r. Purification by silica flash chromatography (2:1 hexanes/EtOAc) yielded the N-propargyl sulfinamide as a sticky brown foam (1.05 g, 63%). TLC: Rf 0.47 (40% EtOAc/hexanes). [alpha] D :-10.4 (c 0.55, CHCl3). IR (ATR): 2958, 2931, 2858, 1590, 1556, 1473, 1428, 1111, 1073, 762, 703. 1H-NMR (600 MHz,): delta 7.67 (ddd, J = 8.1, 2.7, 1.4 Hz, 4H), 7.52 (t, J = 1.7 Hz, 1H), 7.44 (ddd, J = 8.0, 2.0, 1.0 Hz, 1H), 7.43- 7.39 (m, 2H), 7.39- 7.33 (m, 4H), 7.32 (dt, J = 7.7, 1.3 Hz, 1H), 7.16 (t, J = 7.9 Hz, 1H), 4.59 (q, J = 6.9 Hz, 1H), 3.91 (ddd, J = 10.5, 6.6, 5.1 Hz, 1H), 3.86 (ddd, J = 10.5, 6.4, 5.1 Hz, 1H), 3.61 (d, J = 7.4 Hz, 1H), 2.11- 1.96 (m, 2H), 1.21 (s, 9H), 1.06 (s, 9H). 13C- NMR (151 MHz,): delta 135.5, 134.4, 133.3, 133.3, 131.5, 130.4, 129.7, 129.6, 127.7, 127.7, 124.6, 122.0, 90.2, 83.6, 60.3, 56.3, 45.6, 39.5, 26.8, 22.5, 19.2. HRMS m/z calcd for C31H38NO2NaSiSBr ([M+Na]+) 618.1474; found 618.1462.

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

Reference:
Patent; MEMORIAL SLOAN-KETTERING CANCER CENTER; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; THE BROAD INSTITUTE, INC.; UNIVERSITY OF CENTRAL FLORIDA RESEARCH FOUNDATION, INC.; MCKERROW, James; DANDAPANI, Sivaraman; EDWANKAR, Rahul; TAN, Derek, Shieh; FOLEY, Corinne, N.; MOURA-LETTS, Gustavo; VERANO, Alyssa; CHAKRABARTI, Debopam; ROBERTS, Bracken; (258 pag.)WO2017/124087; (2017); A1;,
Bromide – Wikipedia,
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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. 407-97-6, name is 1-Bromo-5-fluoropentane, This compound has unique chemical properties. The synthetic route is as follows., 407-97-6

To a solution of N-cyclopropyl-1-{4-[(ethylamino)carbonyl]-2-hydroxyphenyl}-1H-1,2,3-triazole-4-carboxamide (0.16 g) obtained in Example 139 in DMF (5 ml) were added 1-bromo-5-fluoropentane (0.11 g) and potassium carbonate (0.07 g), and the mixture was stirred at 50¡ãC overnight. The reaction mixture was allowed to cool to room temperature, and water was added to the reaction mixture. The deposited precipitate was collected by filtration, washed with water, and recrystallized from ethanol-water to give the title compound as a pale-brown powder (0.12 g, 60percent). NMR (CDCl3) delta: 0.68-0.72 (2H, m), 0.86-0.93 (2H, m), 1.29 (3H, t, J = 7.2), 1.52-1.90 (7H, m), 2.93-2.96 (2H, m), 3.51-3.58 (2H, m), 4.19 (2H, t, J = 6.6), 4.45 (2H, td, J = 6.0, 47.3), 6.15 (1H, brs), 7.36 (1H, dd, J = 1.7, 8.3), 7.65 (1H, d, J = 1.7), 7.88 (1H, d, J = 8.3), 8.68 (1H, s).

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; Takeda Pharmaceutical Company Limited; EP1867331; (2007); A1;,
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1647-26-3,Some common heterocyclic compound, 1647-26-3, name is 1-Bromo-2-cyclohexylethane, 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.

Dissolve (2-bromo-ethyl) -cyclohexane (10.0 g, 52.3 mmol) in 500 mL acetone, add sodium iodide (15.6 g, 104.6 mmol) and reflux over night. Filter the reaction mixture, add water to the filtrate and extract with hexane. Dry the organic phases over sodium sulfate, filter and concentrate to an oil. Further purify this material by distillation to afford the title compound (10.6 G). 1H-NMR (CDC13) 8= 0.83-1. 00 (M, 2H), 1.07-1. 48 (M, 4H), 1.61- 1.80 (M, 7H), 3.16-3. 27 (M, 2H).

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-cyclohexylethane, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; WO2004/63179; (2004); A1;,
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