2-(3-iodophenoxy)-N,N-dimethylethanamine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Stirred a solution of 3-(2-Dimethylaminoethoxy)phenyl iodide (0.495 g, 1.70 mmoles), 4-carboxybenzeneboronic acid (Lancaster, 0.282 g, 1.70 mmoles), and sodium carbonate (0.360 g, 3.40 mmoles) in 1:1 H2O: AcCN (20 mL) under vacuum for five minutes, followed by the addition of tetrakis(triphenylphosphine)palladium (0) (0.170g). The reaction mixture was heated (90° C.) for three hours, and the catalyst was filtered off through Celite. The effluent was concentrated slightly to remove the AcCN, and the resulting aqueous solution was acidified with 2N HCl and purified on an HPLC to yield 0.462 g of the title compound as the TFA salt. MS (ion spray) m/z 286 (M+H)+. the catalyst was filtered off through Celite The effluent was concentrated slightly to remove the AcCN purified on an HPLC