Category: 3814-30-0

3814-30-0, 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. 3814-30-0, name is (Bromomethyl)cyclopentane, A new synthetic method of this compound is introduced below.

Preparation 78: 6-Bromo-1 -(cyclopentylmethyl)-2-(1 -methyl-1 H-pyrazol-4-yl)-1 H- pyrrolo[3,2-c]pyridine; [00248] Sodium hydride (60% in mineral oil, 10.8mg, 0.271 mmol) was added to a solution of 6-bromo-2-(1 -methyl-1 H-pyrazol-4-yl)-1 H-pyrrolo[3,2-c]pyridine (Preparation 22, 50mg, 0.180mmol) in DMF (780ml_). The reaction mixture was then stirred for 15 minutes at room temperature before the addition of (bromomethyl)cyclopentane (44mg, 0.271 mmol). The reaction mixture was then stirred overnight at room temperature and for 24 hours at 60C. Sodium hydride (60% in mineral oil, 5mg, 0.125mmol) was added and the reaction was stirred for another 7 hours at 60C. The reaction mixture was then diluted with water and EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2S04), filtered and concentrated under reduced pressure. The crude was purified via Biotage silica gel column chromatography eluting with (DCM/EtOAc 99/1 to 80/20) to afford the title product as a colourless oil (45mg, 69%). 1 H NMR (500 MHz, CDCI3) d 1 .10-1 .19 (m, 2H), 1 .46-1 .64 (m, 6H), 2.24-2.33 (m, 1 H), 4.03 (s, 3H), 4.09 (d, J = 7.6Hz, 2H), 6.53 (d, J = 0.9Hz, 1 H), 7.45 (t, J = 0.9Hz, 1 H), 7.59 (s, 1 H), 7.68 (s, 1 H), 8.60 (d, J = 0.9Hz, 1 H). LC (Method B)-MS (ESI, m/z) fR 3.03 min, 359 [(M+H+), 100%].

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; CANCER RESEARCH TECHNOLOGY LIMITED; BAVETSIAS, Vassilios; ATRASH, Butrus; NAUD, Sebastien Gaston Andre; SHELDRAKE, Peter William; BLAGG, Julian; WO2012/123745; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 3814-30-0

EXAMPLE 136 4-(4-Chloro-3-cyclopentylmethylsulfamoylphenyl)-3-methyl-2-methylimino-1,3-thiazolidine-4-ole 6.7 g of 4-(4-Chloro-3-sulfamoylphenyl)-3-methyl-2-methylimino-1,3-thiazolidine-4-ole (Example 2) were introduced, while stirring, into a mixture of 10 ml of absolute dimethyl sulfoxide and 1.2 g of pulverized potassium hydroxide with the exclusion of nitrogen, the temperature being maintained between 8 C and 12 C by outward cooling. While cooling and stirring were maintained, 3.3 g of cyclopentylmethylbromide were added dropwise, the mixture was stirred for 10 hours at room temperature and precipitated with 100 ml of water. The oily residue was decanted, the amorphous product was solidified under 100 ml of fresh water, suction-filtered and washed with water several times. Yellow-brown solid substance, decomposition beginning at 72 C. The IR-spectrum was identical with that of Example 76.

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 3814-30-0.

Reference:
Patent; Hoechst Aktiengesellschaft; US4061761; (1977); A;,
Bromide – Wikipedia,
bromide – Wiktionary

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 3814-30-0 name is (Bromomethyl)cyclopentane, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 3814-30-0

EXAMPLE 51A Methyl 3-cyclopentyl-2-methyl-2-phenylpropanoate A solution of lithium bis(trimethylsilyl)amide (1M in tetrahydrofuran, 3.04 mL, 3.04 mmol, 1 equiv) under a N2 atmosphere was cooled to 0 C. and treated with a solution of methyl 2-phenylpropionate (0.500 g, 3.04 mmol, 1 equiv) in dry tetrahydrofuran (2 mL). The reaction was stirred at 0 C. for 2 hrs, then cooled to -78 C. and treated with hexamethylphosphoric triamide (0.4 mL) and bromomethylcyclopentane (0.745 g, 4.568 mmol, 1.5 equiv). Stirred the reaction at -78 C. and allowed the bath to slowly warm to room temperature overnight. After 15 hrs, the reaction mixture was quenched with 10% aq NH4Cl (50 mL) and extracted with ethyl acetate (100 mL). The organic extract was washed with H2O (50 mL) and brine, then dried over Na2SO4, filtered, and concentrated by rotary evaporation. The residue was purified by SiO2 flash chromatography with 2:3 dichloromethane/hexanes to give the product as colorless oil (1.38 g, 5.60 mmol, 92%). 1H NMR (300 MHz, DMSO-d6): delta ppm 0.90-1.12 (m, 2H) 1.32-1.72 (m, 10H) 1.97-2.12 (m, 2H) 3.58 (s, 3H) 7.19-7.35 (m, 5H); MS (APCI+) m/z 247 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (Bromomethyl)cyclopentane, and friends who are interested can also refer to it.

Reference:
Patent; Hutchinson, Douglas K.; Bellettini, John R.; Betebenner, David A.; Bishop, Richard D.; Borchardt, Thomas B.; Bosse, Todd D.; Cink, Russell D.; Flentge, Charles A.; Gates, Bradley D.; Green, Brian E.; Hinman, Mira M.; Huang, Peggy P.; Klein, Larry L.; Krueger, Allan C.; Larson, Daniel P.; Leanna, M. Robert; Liu, Dachun; Madigan, Darold L.; McDaniel, Keith F.; Randolph, John T.; Rockway, Todd W.; Rosenberg, Teresa A.; Stewart, Kent D.; Stoll, Vincent S.; Wagner, Rolf; Yeung, Ming C.; US2005/107364; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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;,
Bromide – Wikipedia,
bromide – Wiktionary

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;,
Bromide – Wikipedia,
bromide – Wiktionary