Toluene → 3-[3-(2-Benzoimidazol-1-ylacetyl)phenyl]-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-[2-(3-bromophenyl)ethyl]-1H-imidazole (51.5 mg, 0.205 mmol; see step (a)) in toluene (10 mL) and ethanol (1 mL) was added 5-isobutyl-2-(N-tert-butylaminosulfonyl)thiophene-3-boronic acid (111.3 mg, 0.349 mmol; see Example 1(c)), Pd(PPh3)4 (14.2 mg, 23.4 μmol) and Na2CO3 (410 μL, 0.820 mmol, 2.0 M aq), and the reaction mixture was stirred for 4 h at 90° C. The reaction mixture was diluted with water (10 mL) and extracted with EtOAc. The combined organic phase was dried (over anhydrous MgSO4), concentrated in vacuo, and the residue was purified by flash chromatography using EtOAc:hexane (3:7) as eluent to give the sub-title compound in 91% yield (83.3 mg, 0.187 mmol).

Provenance & Evidence