Water → HCID 71293803, compound

Participants

Reaction Steps

To a 500 mL round-bottomed flask equipped with a water condensor is added (S)-4-(6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)-3-fluorobenzonitrile (6.0 g, 26.3 mmol) and pyridine (32.6 mL). To the solution is added iron(III) chloride (0.21 g, 1.32 mmol and tert-butyl hydroperoxide (10.9 mL, 79 mmol). The reaction is heated to reflux and stirred for 5 hours. The reaction is allowed to cool to room temperature and is then filtered through celite. The collect filtrate is concentrated under reduced pressure. The obtained residue is purified by RP-HPLC (XBridge, C8 H2O (0.1% NH4OH)/CH3CN) to give 1.5 g of the entitled product. MS (m+1)=242.1; LCMS condition B, retention time=0.97 min; 1H NMR (400 MHz, CDCl3) δ ppm 3.12 (dd, 1H), 3.80 (dd, 1H), 6.04 (dd, 1H), 7.14 (t, 1H), 7.48-7.57 (m, 2H), 7.61 s, 1H, 7.72 s, 1H.

Provenance & Evidence