Sodium Carbonate → tert-butyl N-[4-[3-(3-aminophenyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Participants

Reaction Steps

Following the same procedure as in Example 1, step c, reaction of 3-amino-phenyl boronic acid (27 mg, 0.2 mmol), {[4-(3-bromo-benzenesulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (50 mg, 0.1 mmol, as prepared in Example 27, step c), tetrakis(triphenylphosine)palladium(0) (29 mg, 0.025 mmol, Strem Chemicals Inc, Newburyport, Mass.), Na2CO3 (400 μL, 2M), and toluene/EtOH mixture (2:1, 1.2 mL) afforded 35 mg (70%) after purification (SiO2, flash elution: 30% EtOAc in hexanes) of the title compound as a white foam. ESI-MS (m/z): Calcd. for C23H25N3O4S3: 503.6; found: 503.9, 404.1 (M−Boc).

Provenance & Evidence