Diiodomethane → HCID 90332612, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-2-(cyclopent-1-en-1-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (600 mg, 1.40 mmol) and ZnEt2 (15 mL, 14.04 mmol) in DCM (10 mL) was added dropwise CH2I2 (1.2 mL, 14.04 mmol) at 0° C., and then the mixture was stirred at 25° C. After 3 hours, 10 mL NH4Cl (a.q.) was added, and the mixture was extracted with DCM (30 mL*3), and dried over Na2SO4. After concentration, the residue was purified by column chromatography (DCM:EtOAc=3:1) to give the product of 2-(bicyclo[3.1.0]hexan-1-yl)-5-bromo-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (300 mg, yield: 48%). 1H-NMR (CDCl3, 400 MHz) δ 8.30 (s, 1H), 7.60 (s, 1H), 6.16 (d, J=2.0 Hz, 1H), 3.34 (s, 3H), 3.12 (d, J=4.8 Hz, 3H), 3.07 (s, 3H), 2.10˜2.21 (m, 2H), 2.01˜2.09 (m, 2H), 1.86˜1.99 (m, 2H), 1.38˜1.46 (m, 1H), 1.37 (d, J=4.0 Hz, 2H). MS (M+H)+: 441/443.

Provenance & Evidence