Trimethylsilyl iodide → HCID 178523841, compound

Participants

Reaction Steps

To a solution of Example 19 (31.2 mg, 0.076 mmol) in CH2Cl2 (506 μl) at 0° C. was added iodotrimethylsilane (20.6 μl, 0.152 mmol). The mixture was stirred at room temperature for overnight. Second portion of TMSI was added and the reaction was heated to 50° C. for 2 h. The reaction mixture was quenched w/H2O, extracted w/EtOAc. The combined organic layers were dried (Na2SO4), filtered, cone. The residue was purified by reverse phase HPLC (C-18 column, 3-70% MeCN in H2O with both containing 0.05% TFA) to provide the title compound. 1H NMR (400 MHz, CDCl3) δ 8.41 (d, J=6.8 Hz, 1H), 8.16 (s, 1H), 7.75 (dd, J=2.4, 9.2 Hz, 1H), 7.83 (d, J=9.2 Hz, 1H), 7.63 (dt, J=4.8, 8.0 Hz, 1H), 7.50 (dd, J=8.0, 10.0 Hz, 1H), 7.45 (s, 1H), 6.92 (d, J=8.4 Hz, 1H), 4.41 (s, 2H), 4.13 (dd, J=4.8, 11.2 Hz, 1H), 4.07-4.03 (m, 1H), 3.76 (dt, J=4.8, 9.6 Hz, 1H), 3.52 (dt, J=2.4, 11.6 Hz, 1H), 3.28 (dd, J=10.0, 11.2 Hz, 1H), 2.15-2.10 (m, 1H), 1.95-1.85 (m, 1H). HRMS (ES) [M+1]+ calcd for C22H21FN3O4: 398.1517, Found: 398.1511.

Provenance & Evidence