Hydrochloric Acid → HCID 68514417, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve the compound of Example 22 (160 mg, 0.29 mmol) in CH2Cl2 (5 mL) and cool the solution to −78° C. Add HCl (0.2 mL, 2.0 M in diethyl ether (Et2O)) and stir the reaction mixture for 10 minutes. Remove the solvent under reduced pressure and then dissolve the solid in CH2Cl2 (5 mL) under N2. Cool the solution to 0° C. and add BBr3 (370 mg, 1.46 mmol). Stir the reaction for one hour and add water (20 mL). Extract the aqueous layer with CH2Cl2 (3×20 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash column chromatography (silica gel, 2-8% MeOH—NH4OH (10/1, v/v)/CH2Cl2) to give 6-(1,1-dioxo-2,3-dihydro-1H-1λ6-benzo[b]thiophen-5-yl)-5-[4-(2-piperidin-1-yl-ethoxy)-phenoxy]-naphthalen-2-ol. Dissolve the free base in CH2Cl2 (5 mL) and cool to −78° C. Add HCl (0.5 mL, 2.0 M in Et2O) and stir the solution for 10 minutes. Remove the solvent under reduced pressure to give a solid. Dry the solid at 40° C., overnight, in vacuo to give 42 mg of the title compound (27%): mass spectrum (ion spray): m/z=530.3 (M+H).

Provenance & Evidence