Category: 1114546-30-3

Ahmed, Saleh et al. published their research in Journal of Medicinal Chemistry in 2017 | CAS: 1114546-30-3

4-Bromo-2-fluoro-3-methylbenzonitrile (cas: 1114546-30-3) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).SDS of cas: 1114546-30-3

1,2,4-Triazolo-[1,5-a]pyridine HIF Prolylhydroxylase Domain-1 (PHD-1) Inhibitors With a Novel Monodentate Binding Interaction was written by Ahmed, Saleh;Ayscough, Andrew;Barker, Greg R.;Canning, Hannah E.;Davenport, Richard;Downham, Robert;Harrison, David;Jenkins, Kerry;Kinsella, Natasha;Livermore, David G.;Wright, Susanne;Ivetac, Anthony D.;Skene, Robert;Wilkens, Steven J.;Webster, Natalie A.;Hendrick, Alan G.. And the article was included in Journal of Medicinal Chemistry in 2017.SDS of cas: 1114546-30-3 This article mentions the following:

Herein the authors describe the identification of 4-{[1,2,4]triazolo[1,5-a]pyridin-5-yl}benzonitrile-based inhibitors of the hypoxia-inducible factor prolylhydroxylase domain-1 (PHD-1) enzyme. These inhibitors were shown to possess a novel binding mode by x-ray crystallog., in which the triazolo N1 atom coordinates in a hitherto unreported monodentate interaction with the active site Fe2+ ion, while the benzonitrile group accepts a hydrogen-bonding interaction from the side chain residue of Asn 315. Further optimization led to potent PHD-1 inhibitors with good physicochem. and pharmacokinetic properties. In the experiment, the researchers used many compounds, for example, 4-Bromo-2-fluoro-3-methylbenzonitrile (cas: 1114546-30-3SDS of cas: 1114546-30-3).

4-Bromo-2-fluoro-3-methylbenzonitrile (cas: 1114546-30-3) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).SDS of cas: 1114546-30-3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

9/29/2021 News Some tips on 1114546-30-3

The synthetic route of 4-Bromo-2-fluoro-3-methylbenzonitrile has been constantly updated, and we look forward to future research findings.

These common heterocyclic compound, 1114546-30-3, name is 4-Bromo-2-fluoro-3-methylbenzonitrile, 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. Quality Control of 4-Bromo-2-fluoro-3-methylbenzonitrile

General procedure: A mixture of 4-bromo-2-fluoro-3-methylbenzonitrile (7.00 g, 32.7mmol), potassium vinyltrifluoroborate (5.3 g, 39 mmol) and Pd(dppf)Cl2 (0.5 g, 0.7 mmol) in 70 mL of EtOH and 30mL of TEA was refluxed under Ar for 4 hours. Concentrated, the residue was purified by column chromatography(petrol ether: EtOAc = 10 :1) to afford 4-ethenyl-2-fluoro-3-methylbenzonitrile.

The synthetic route of 4-Bromo-2-fluoro-3-methylbenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Corp.; PASTERNAK, Alexander; BLIZZARD, Timothy; CHOBANIAN, Harry; DE JESUS, Reynalda; DING, Fa-Xiang; DONG, Shuzhi; GUDE, Candido; KIM, Dooseop; TANG, Haifeng; WALSH, Shawn; PIO, Barbara; JIANG, Jinlong; (128 pag.)EP2744499; (2016); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Extended knowledge of 4-Bromo-2-fluoro-3-methylbenzonitrile

The synthetic route of 1114546-30-3 has been constantly updated, and we look forward to future research findings.

Synthetic Route of 1114546-30-3,Some common heterocyclic compound, 1114546-30-3, name is 4-Bromo-2-fluoro-3-methylbenzonitrile, molecular formula is C8H5BrFN, 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 mixture of 4-bromo-2-fluoro-3- methylbenzonitrile (7.0 g, 32.7 mmol), potassium vinyltrifluoroborate (5.3 g, 39.3 mmol), Pd(dppf)Cl2 (0.5 g, 0.7 mmol) and TEA (30 mL) in EtOH (70 mL) was refiuxed under Ar for 4 hours. After being cooled to room temperature, the reaction mixture was concentrated and the residue was purified by column chromatography (petrol ether : EtOAc = 10 : 1) to afford 2- fluoro-3-methyl-4-vinylbenzonitrile as a white solid.

The synthetic route of 1114546-30-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; PIO, Barbara; CHOBANIAN, Harry, R.; SHI, Zhi-Cai; DONG, Shuzhi; GUO, Yan; WALSH, Shawn, P.; GUO, Zhiqiang; FERGUSON, Ronald, D.; CATO, Brian; (114 pag.)WO2016/60941; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some tips on 4-Bromo-2-fluoro-3-methylbenzonitrile

The synthetic route of 4-Bromo-2-fluoro-3-methylbenzonitrile has been constantly updated, and we look forward to future research findings.

These common heterocyclic compound, 1114546-30-3, name is 4-Bromo-2-fluoro-3-methylbenzonitrile, 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. Recommanded Product: 1114546-30-3

General procedure: A mixture of 4-bromo-2-fluoro-3-methylbenzonitrile (7.00 g, 32.7mmol), potassium vinyltrifluoroborate (5.3 g, 39 mmol) and Pd(dppf)Cl2 (0.5 g, 0.7 mmol) in 70 mL of EtOH and 30mL of TEA was refluxed under Ar for 4 hours. Concentrated, the residue was purified by column chromatography(petrol ether: EtOAc = 10 :1) to afford 4-ethenyl-2-fluoro-3-methylbenzonitrile.

The synthetic route of 4-Bromo-2-fluoro-3-methylbenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Corp.; PASTERNAK, Alexander; BLIZZARD, Timothy; CHOBANIAN, Harry; DE JESUS, Reynalda; DING, Fa-Xiang; DONG, Shuzhi; GUDE, Candido; KIM, Dooseop; TANG, Haifeng; WALSH, Shawn; PIO, Barbara; JIANG, Jinlong; (128 pag.)EP2744499; (2016); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Share a compound : 4-Bromo-2-fluoro-3-methylbenzonitrile

The synthetic route of 1114546-30-3 has been constantly updated, and we look forward to future research findings.

Application of 1114546-30-3, These common heterocyclic compound, 1114546-30-3, name is 4-Bromo-2-fluoro-3-methylbenzonitrile, 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.

Reference Example 3 4-[(2S,3S)-3-(tert-butyldimethylsilyloxy)-2-methyl-5-oxopyrrolidin-1-yl]-2-fluoro-3-methylbenzonitrile To a solution of 4-bromo-2-fluoro-3-methylbenzonitrile (1.10 g), (4S,5S)-4-(tert-butyldimethylsilyloxy)-5-methylpyrrolidin-2-one (1.18 g), cesium carbonate (2.51 g), tris(dibenzylideneacetone)dipalladium(0) (235 mg) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (297 mg) in dioxane (30 mL) was stirred under an argon atmosphere at 80 C. for 8 hr. 5 The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound as a colorless solid (yield: 347 mg, 19%). 1H-NMR(CDCl3)delta:0.11(6H,d,J=7.2 Hz), 0.91(9H,s), 1.04(3H,d,J=6.4 Hz), 2.19(3H,d,J=2.3 Hz), 2.50(1H,dd,J=16.8,2.4 Hz), 2.78(1H,dd,J=16.8,5.4 Hz), 4.09-4.22(1H,m), 4.44-4.50(1H,m), 6.96(1H,d,J=8.7 Hz), 7.45-7.53(1H,m).

The synthetic route of 1114546-30-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; US2009/42967; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts