Diisopropylethylamine → 4-(5-{3-[3-(4-Fluorophenyl)prop-1-ynyl]phenyl}tetrazol-2-ylmethyl)benzene-sulfonic acid

Participants

Reaction Conditions

Reaction Steps

A suspension of 4-[5-(3-bromophenyl)tetrazol-2-ylmethyl]benzenesulfonic acid, sodium salt (0.50 g, 1.27 mmol) in DMF (3 mL) was treated with diisopropylethylamine (0.88 mL, 5.1 mmol), palladium tetrakis(triphenylphosphine) (“Pd(PPh3)4”, 0.29 g, 0.25 mmol), CuI (cat), and 1-fluoro-4-prop-2-ynyl-benzene (0.42 g, 3.1 mmol), and the mixture degassed with nitrogen. The reaction mixture was heated in the microwave for 15 minutes at 100° C., cooled to room temperature, poured into 1N HCl, extracted with EtOAc, washed with brine, dried over MgSO4, and evaporated onto silica gel. The mesh was purified on a 3.5×15 cm silica gel column eluted with ethyl acetate (“EtOAc”)-methanol (“MeOH”) 4:1 with 1% acetic acid (“AcOH”). Evaporation and trituration with ether afforded 0.052 g of orange solid (8.26% yield) NMR (DMSO-d6); 8.03–7.99 (m, 1H), 7.61–7.51 (m, 6H), 7.46–7.42 (dd, 1H), 7.36–7.33 (d, 2H), 7.19–7.15 (t, 2H), 5.98 (s, 2H), 3.90 (s, 2H)

Provenance & Evidence