Reaktion #2386483

Reaktionsgleichung

N-(4-chlorobenzyl)-2-iodo-7-methyl-4-oxo-4,7-dihydro-thieno[2,3-b]pyridine-5-carboxamide

propargyl alcohol

→

title compound

Ausbeute 77.0%

N-(4-Chlorobenzyl)-2-(3-hydroxy-1-propynyl)-7-methyl-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide

Ausbeute 77.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe diethylamine is removed in vacuo
2. 2
   Sonstigethe resulting brown solid is purified via column chromatography (CH2Cl2:CH3OH; 98:2)
3. 3
   Einengenconcentrated in vacuo
4. 4
   Sonstigeto yield an orange solid which
5. 5
   Sonstigeis recrystallized from ethanol

Vorschrift

To a suspension of N-(4-chlorobenzyl)-2-iodo-7-methyl-4-oxo-4,7-dihydro-thieno[2,3-b]pyridine-5-carboxamide (Example No. 23) (1.632 g) in diethylamnine (40 mL) is added copper iodide (0.210 g) and Pd(PPh3)2Cl2 (0.125 g) followed by addition of propargyl alcohol (0.29 mL). The reaction is stirred at rt for 18 h. The diethylamine is removed in vacuo and the resulting brown solid is purified via column chromatography (CH2Cl2:CH3OH; 98:2). Fractions homogeneous by TLC are combined and concentrated in vacuo to yield an orange solid which is recrystallized from ethanol to yield 1.06 g (77%) of the title compound as a yellow solid.

Quelle