Diiodomethane → HCID 58827088, compound

Participants

Reaction Steps

A solution of TFA (0.234 mL, 3 mmol) in 0.6 mL of dry CH2Cl2 is added dropwise to a solution of Et2Zn (1M in Hexanes, 3.06 mL, 3.06 mmol) at 0° C. The resulting suspension is subsequently treated with a solution of CH2I2 (0.246 mL, 3.06 mmol) in CH2Cl2 (0.4 mL). After 2 h at 0° C., a solution of 3-fluoro-4-(7-methylene-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)benzonitrile (333.8 mg, 1.392 mmol) in CH2Cl2 is added. After overnight, the reaction is quenched with saturated NaHCO3 solution, and extracted with CH2Cl2 (20 mL×4). The combined extracts are washed with brine, dried over anhydrous Na2SO4. After filtration and evaporation, the residue is purified by chromatography and yield 112 mg of oil. MS (ESI) m/z 254.2 (M+H). 1H NMR (400.3 MHz, CDCl3): δ 8.93 (s, 1H), 7.54-7.52 (m, 1H), 7.45 (d, J=8.00 Hz, 1H), 7.35 (m, 1H), 6.83 (s, 1H), 6.27 (brs, 1H), 3.22 (m, 1H), 2.61 (d, J=12 Hz, 1H), 1.33-1.19 (m, 2H), 1.16-1.14 (m, 1H), 0.90-0.85 (m, 1H).

Provenance & Evidence