Acetone → 7-Iodo-1,1-dimethyl-1,2,3,4-tetrahydro-benzo[4,5]furo[2,3-c]pyridine

Participants

Reaction Steps

To a solution of 2-(6-iodo-benzofuran-3-yl)-ethylamine (4.20 g, 14.63 mmol) in methanol (60.0 mL, 1.48 mol) was added acetone (1.63 mL) and the reaction mixture was stirred at rt. After 2 days the solvent was evaporated. The residue was dissolved in a mixture of TFA (7.0 mL) and DCE (70.0 mL) and heated to reflux. After 20 h the reaction mixture was cooled down and basified with 5M aq. NaOH. The layers were separated and the aqueous phase extracted with DCM. The combined organic layers was dried (Na2SO4) and the solvent was evaporated. The residue was purified on a silica gel column eluting with DCM-MeOH—NH4OH to afford 7-iodo-1,1-dimethyl-1,2,3,4-tetrahydro-benzo[4,5]furo[2,3-c]pyridine as an off-white solid. mp 97-98° C.; MS m/z 328 [M+H]+.

Provenance & Evidence