Reaktionsgleichung
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12](OS(C(F)(F)F)(=O)=O)[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].[CH3:24][O:25][CH2:26][C:27]#[CH:28].C(N(CC)CC)C.C(OCC)(=O)C.CCCCCC>CN(C=O)C.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>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([C:28]#[C:27][CH2:26][O:25][CH3:24])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]Komponenten
7
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 90 °C
Versuchsvorschrift
To the product of Example 20, Step 1, 3-methyl-4-trifluoromethanesulfonyloxy-benzofuran-2-carboxylic acid ethyl ester (860 mg, 2.4 mmol, 1 eq), in 7 mL of DMF under nitrogen was added 98 mg of PdCl2(PPh3)2 (0.14 mmol, 0.06 eq), 0.42 mL of 3-methoxy-propyne (5.0 mmol, 2.1 eq) and 1.36 mL of triethylamine (9.7 mmol, 4.0 eq). The reaction mixture was heated to 90° C. for 18 h. After work up and column chromatography (4% ethyl acetate/hexane), 4-(3-methoxy-prop-1-ynyl)-3-methyl-benzofuran-2-carboxylic acid ethyl ester was obtained in 53% yield (343 mg). 1H NMR (400 MHz, CDCl3) δ ppm 1.4 (t, J=7.2 Hz, 3 H) 2.8 (t, 3 H) 3.5 (s, 3 H) 4.4 (s, 2 H) 4.5 (q, J=7.2 Hz, 2 H) 7.4 (m, 2 H) 7.5 (dd, J=7.7, 1.6 Hz, 1 H)
Quellen und Nachweise
- ORD-Eintrag
- ord-0ac7317bcc5943bca318ec231f53062c
- Quelldatensatz
- uspto-grants-2008_09
- Patentnummer
- US07420001B2
Verknüpfte Notizen
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