N-BOC-ethylenediamine → (2-{3-[5-(1H-Indol-2-yl)-2-methoxy-phenyl]-thioureido}-ethyl)-carbamic acid tert-butyl ester

Participants

Reaction Steps

The product from Example 26, Step A, [5-(1H-indol-2-yl)-2-methoxy-phenyl]-isothiocyanate, (0.272 g, 1.0 mmol) and mono-tert-butyloxycarbonyl ethylenediamine (0.156 g, 1.0 mmol) were heated briefly to 50° C. in ethyl acetate (20 mL). The reaction mixture was allowed to stand 1 hour at room temperature and was then concentrated. The residue was filtered through silica gel using hexanes/ethyl acetate as eluant The purest product-containing factions were combined, concentrated, and triturated with 3/1, hexanes/ethyl acetate, v/v, to give the product as an off-white solid (0.09 g), mp 159-160° C.

Provenance & Evidence