Trimethylsilylacetylene → 2-(2-((Trimethylsilyl)ethynyl)phenyl)propanamide

HRID 592356Notizen

Reaktionsgleichung

I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH3:12])[C:9]([NH2:11])=[O:10].F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.[CH3:31][Si:32]([C:35]#[CH:36])([CH3:34])[CH3:33]>CN(C=O)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:31][Si:32]([C:35]#[C:36][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH3:12])[C:9]([NH2:11])=[O:10])([CH3:34])[CH3:33]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

A mixture of 2-(2-iodophenyl)propanamide I13 (16.5 g, 0.060 mol), CuI (0.229 g, 1.20 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.348 g, 1.20 mmol), PdCl2(PPh3)2 (0.421 g, 0.600 mmol) and trimethylsilylacetylene (10.3 mL, 0.072 mol) in DMF (60 mL) was bubbled with N2 for 10 minutes. Et3N (50 mL) was then added and the mixture was stirred under nitrogen at 60° C. for 5 hours. The reaction mixture was cooled and the volatiles were removed in vacuo. The dark brown residue was adsorbed onto silica and purified by column chromatography (Biotage Isolera, 120 g SiO2 cartridge, 0-30% EtOAc in petroleum benzine 40-60° C.) to give the title compound I15 as an orange oil (11.5 g, 78%). LCMS-D: rt 3.49 min; m/z 246 [M+H]+.

Aufarbeitung

customwas bubbled with N2 for 10 minutes
additionEt3N (50 mL) was then added
temperatureThe reaction mixture was cooled
customthe volatiles were removed in vacuo
custompurified by column chromatography (Biotage Isolera, 120 g SiO2 cartridge, 0-30% EtOAc in petroleum benzine 40-60° C.)

Quellen und Nachweise

ORD-Eintrag: ord-d60519605f4f4474a60e4e6da7644cdf
Quelldatensatz: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09238644B2

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