2-Fluoro-5-methylphenyl isocyanate → Dimethyl 5,5'-{N-[(6-amino-5-{[3-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenyl]ethynyl}pyridin-3-yl)carbonyl]sulfonimidoyl}dipentanoate

Participants

Reaction Steps

The reaction solution of dimethyl 5,5′-[N-({6-amino-5-[(3-aminophenyl)ethynyl]pyridin-3-yl}carbonyl)sulfonimidoyl]dipentanoate (140 mg, 0.265 mmol, 1.0 equiv.) and 2-fluoro-5-methylphenyl isocyanate (38.8 μL, 0.292 mmol, 1.1 equiv.) in DMF (3 mL) was stirred at room temperature for 3 hours. It was then diluted with EtOAc, washed with sat. aq. NaHCO3, aq. NH4Cl, and brine, and finally dried with anhydrous Na2SO4. The solution was decanted, concentrated, and the oily residue was subject to a gradient column chromatography (from EtOAc-Hex 1:5 to 5:1) yielding the title compound as clear oil (169 mg). 1H NMR (DMSO-d6) δ: 9.14-9.15 (m, 1H), 8.56 (d, J=2.3 Hz, 1H), 8.54 (d, J=2.3 Hz, 1H), 8.04 (d, J=2.1 Hz, 1H), 7.99 (dd, J=7.9, 1.8 Hz, 1H), 7.81 (t, J=−1.8 Hz, 1H), 7.40 (dt, J=7.7, 1.9 Hz, 1H), 7.30-7.35 (m, 2H), 7.11 (dd, J=11.3, 8.4 Hz, 1H), 7.00 (br. s., 2H), 6.79-6.83 (m, 1H), 3.52-3.64 (m, 10H), 2.39 (t, J=7.3 Hz, 4H), 2.27 (s, 3H), 1.72-1.85 (m, 4H), 1.65-1.71 (m, 4H)

Provenance & Evidence