Trimethylsilyl iodide → HCID 76684540, compound

Participants

Reaction Conditions

Reaction Steps

Into a glass vial containing the product from step (b) (71 mg, 0.195 mmol) dissolved in CHCl3 (2 ml), TMSI (266 μL, 1.95 mmol) was added. The reaction mixture was heated to 60° C. for 4 hours. The volatiles were evaporated in vacuo and the residue was dissolved in 2M HCl (3 ml) and water (20 ml). The aqueous mixture was washed with diethyl ether (2×). The aqueous layer was then basified with 2M NaOH to pH 10 and extracted with DCM (3×). The combined DCM extracts were washed with brine, dried over Na2SO4, and solvent evaporated in vacuo gave the crude product. Purification by preparative reverse phase HPLC gave the title compound as a colorless oil (9.9 mg). 1H NMR (300 MHz, CDCl3) δ 8.66 (bs, 1H); 7.41-7.26 (m, 5H); 7.00 (s, 1H); 3.31-3.15 (m, 8H); 2.84 (t, J=7.5 Hz, 2H); 1.89 (t 7.2 Hz, 2H); 1.33 (s, 6H); MS: ESI (positive): 328 (M+H).

Provenance & Evidence