5-Benzyloxyindole → HCID 69663370, compound

Participants

Reaction Steps

5-Benzyloxyindole (500 mg, 2.24 mmol) was dissolved in THF (20 mL) and treated with 1M KOtBu in THF (2.24 mL, 2.24 mmol). After stirring for 3 hours, N-(bromomethyl) phthalimide (538 mg, 2.24 mmol) was added and the reaction mixture was stirred for an additional 24 hrs. Standard aqueous workup and purification by silica gel chromatography, eluting with 3:1 hexane/ethyl acetate, provided N-(methylenephthalimido)-5-benzyloxyindole (650 mg, 76%). 1H NMR (200 MHz, CDCl3) δ 7.83 (d, J=5.5 Hz, 1H), 7.81 (d, J=5.5 Hz, 1H), 7.72–7.65 (m, 2H), 7.45 (m, 1H), 7.42 (d, 3.0 Hz, 2H), 7.40–25 (m, 2H), 7.09 (d, J=2.2 Hz, 1H), 7.00 (dd, J=2.2, 9.0 Hz, 1H), 6.49 (d, J=3.2 Hz, 1H), 5.91 (s, 2H), 5.07 (s, 2H). MS (EI. m/z) M+=382.

Provenance & Evidence