Trifluoroacetic acid → HCID 76684443, compound

Participants

Reaction Steps

Into a glass vial, the product from step (c) (112 mg, 0.251 mmol) dissolved in 2 ml DCM was added. To this stirred solution, triethylsilane (603 μL, 3.77 mmol) was added, followed by TFA (290 μL, 3.77 mmol). After stirring at room temperature for 16 hours, additional triethylsilane (603 μL, 3.77 mmol) and TFA (290 μL, 3.77 mmol) were added. The reaction mixture was stirred for an additional 16 hours. The volatiles were then evaporated in vacuo and the residue diluted with 2M HCl (20 ml). The aqueous mixture was washed with diethyl ether (2×), 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 to give the title compound as a white semi-solid (52 mg). 1H NMR (300 MHz, CDCl3) δ 7.23-7.20 (m, 1H); 7.08-7.02 (m, 2H); 6.95-6.91 (m, 1H); 6.78 (t, J=7.5 Hz, 1H); 6.51 (bs, 1H); 5.15 (d, J=21.0 Hz, 1H); 3.91 (s, 3H); 3.47-3.28 (m, 2H); 2.97-2.81 (m, 4H); 2.72-2.62 (m, 2H); 2.51-2.46 (2H); 1.68 (bs, 1H); MS: ESI (positive): 330 (M+1).

Provenance & Evidence