2-Acetyl-5-bromothiophene → 1-{5-[2-(4-Isopropoxyphenoxy)-1,3-thiazol-5-yl]thien-2-yl}ethanone

HRID 404868

Reaktionsgleichung

[O:1]([C:8]1[CH:32]=[CH:31][C:11]([O:12][C:13]2[S:14][C:15]([Sn](CCCC)(CCCC)CCCC)=[CH:16][N:17]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=CC=C[CH:3]=1.Br[C:34]1[S:38][C:37]([C:39](=[O:41])[CH3:40])=[CH:36][CH:35]=1>CN(C)C=O.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>[CH:2]([O:1][C:8]1[CH:9]=[CH:10][C:11]([O:12][C:13]2[S:14][C:15]([C:34]3[S:38][C:37]([C:39](=[O:41])[CH3:40])=[CH:36][CH:35]=3)=[CH:16][N:17]=2)=[CH:31][CH:32]=1)([CH3:3])[CH3:7]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

To a degassed solution of Example 2A (550 mg, 1.05 mmol) in N,N-dimethyl formamide (10 mL) at room temperature, was added 1-(5-bromothiophen-2-yl)ethanone (269 mg, 1.31 mmol) followed by dichlorobis(triphenylphosphine)palladium(II) (45 mg, 0.064 mmol). The reaction mixture was heated at 60° C. overnight. The solvent was evaporated under vacuum and the product was purified via silica gel column chromatography using a gradient of 15 to 35% ethyl acetate in hexane to give the desired compound (320 mg). 1H NMR (300 MHz, CDCl3) δ ppm 7.56 (d, J=4.04 Hz, 1H) 7.43 (s, 1H) 7.15-7.24 (m, 2H) 7.02 (d, J=4.04 Hz, 1H) 6.88-6.97 (m, 2H) 4.44-4.62 (heptet, J=5.88 Hz, 1H) 2.54 (s, 3H) 1.36 (d, J=5.88 Hz, 6H). MS (ESI) m/z 360 (M+1)+.

Aufarbeitung

customThe solvent was evaporated under vacuum
customthe product was purified via silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-132afaa0b0264836a1715611f2100295
Quelldatensatz: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08748627B2

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