Diethyl Ether → HCID 67216579, compound

Participants

Reaction Steps

To a solution of 4-((R)-6,6-dimethyl-7-oxo-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)-3-fluoro-benzonitrile (157 mg, 0.45 mmol) in THF cooled to −78° C. was added a 2 M solution of 4-fluoro-phenyl-magnesium bromide in ether (0.39 mL, 0.78 mmol). The crude was allowed to warm to room temperature overnight. The crude was quenched with H2O and diluted in EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated. The crude was purified via flash chromatography first with EtOAc/heptane system followed by MeOH/CH2Cl2 to give 160 mg of the entitled product. MS 366.2 (M+H); LCMS condition B, retention time 1.14 min. 1H NMR (400 MHz, CDCl3) δ ppm 0.88 (s, 3H), 1.00 (s, 3H), 5.45 (s, 1H), 6.92 (t, 1H), 7.04 (s, 1H), 7.05-7.13 (m, 2H), 7.32-7.44 (m, 2H), 7.49 (s, 1H), 7.50-7.58 (m, 2H).

Provenance & Evidence