Reaktion #1706534

Reaktionsgleichung

3-((3-fluorophenyl)ethynyl)-6,7,9,10-tetrahydroazepino[2,1-b]-quinazoline-8,12-dione

THF

→

desired product

3-((3-fluorophenyl)ethynyl)-8-methylene-7,8,9,10-tetrahydroazepino[2,1-b]quinazolin-12(6H)-one

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThen the reaction mixture was quenched with NaOH aqueous
2. 2
   Extraktionextracted with ethyl acetate (3×20 mL)
3. 3
   TrocknenThe combined organic layers were dried over Na2SO4
4. 4
   Einengenconcentrated under reduced pressure

Vorschrift

A solution of 3-((3-fluorophenyl)ethynyl)-6,7,9,10-tetrahydroazepino[2,1-b]-quinazoline-8,12-dione (0.1 g, 0.29 mmol, 1 equiv) and Tebbe Reagent in THF (5 mL) was stirred at rt for half an hour. Then the reaction mixture was quenched with NaOH aqueous and extracted with ethyl acetate (3×20 mL). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to give the desired product, which was purified by silica gel chromatography. MS (ESI): 345 (M+H+); 1H NMR (300 MHz, CDCl3) δ 8.26-8.23 (d, J=8.19 Hz, 1H), 7.78 (s, 1H) 7.58-7.55 (dd, J=8.24, 1.52 Hz, 1H), 7.38-7.32 (m, 2H), 7.28-7.26 (m, 1H), 7.13-7.06 (m, 1H), 4.88-4.86 (d, J=7.50 Hz, 2H), 4.42-4.39 (m, 2H), 3.14-3.10 (m, 2H), 2.61-2.51 (m, 4H). mGluR5 PAM EC50: +++++. Fold shift at 10 μM: ++.

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