Tetrahydrofuran → (E)-N-(Tetrahydro-pyran-2-yloxy)-3-[1-(4-trimethylsilanylethynyl-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylamide

HRID 2408450Notizen

Reaktionsgleichung

I[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([NH:20][O:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][O:23]3)=[O:19])=[CH:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:28][Si:29]([C:32]#[CH:33])([CH3:31])[CH3:30].C(N(CC)CC)C.C1COCC1>[Cu]I.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.CO>[O:23]1[CH2:24][CH2:25][CH2:26][CH2:27][CH:22]1[O:21][NH:20][C:18](=[O:19])/[CH:17]=[CH:16]/[C:13]1[CH:14]=[CH:15][N:11]([S:8]([C:5]2[CH:6]=[CH:7][C:2]([C:33]#[C:32][Si:29]([CH3:31])([CH3:30])[CH3:28])=[CH:3][CH:4]=2)(=[O:10])=[O:9])[CH:12]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

Under nitrogen a microwave vial is charged with (E)-3-[1-(4-Iodo-benzenesulfonyl)-1H-pyrrol-3-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide (5.00 mmol), Trimethylsilylacetylene (6.00 mmol), CuI (0.50 mmol), bis(triphenylphosphine)palladium(II)chloride (0.25 mmol), triethylamine (10.0 mmol) and THF (8 ml). The reaction mixture is heated in a Personal Chemistry Microwave oven at 100° C. for 3600 seconds. Methanol is added to the reaction mixture and the solution is filtered over alumina (10 g, neutral, activity II-III) using MeOH as eluent. After evaporation of the solvent the crude product is purified by prep. HPLC yielding the title compound as yellow powder (2.29 mmol).

Aufarbeitung

filtrationthe solution is filtered over alumina (10 g, neutral, activity II-III)
customAfter evaporation of the solvent the crude product
customis purified by prep

Quellen und Nachweise

ORD-Eintrag: ord-4179b4580faa4818a7a83990c6a2bde3
Quelldatensatz: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08815855B2

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