HCID 67167609, compound → HCID 67167864, compound

Participants

Reaction Steps

2-({4-[3-(trifluoromethyl)diaziridin-3-yl]phenyl}carbonyl)-4-[2-(trimethylsilyl)ethynyl]aniline (66 mg, 0.16 mmol, 1 eq.) was dissolved in diethyl ether (10 mL) and manganese(IV) oxide (300 mg, 3.4 mmol, 21 eq.) was added to the solution. The reaction was stirred at room temperature for 30 minutes and then filtered through Celite with DCM to remove the manganese(IV) oxide. The solvent was evaporated, and the residue was purified on silica column (hexanes/ethyl acetate, 9:1→2:1), resulting in 64 mg (97%) of the title compound as a yellow-orange solid. 1H NMR (500 MHz, CDCl3) δ 7.63 (d, J=8.4, 2H, Ar—H), 7.46 (d, J=1.7, 1H, Ar—H), 7.37 (dd, J=1.8, 8.6, 1H, Ar—H), 7.28 (d, J=8.2, 2H, Ar—H), 6.64 (d, J=8.6, 1H, Ar—H), 6.30 (s, 2H, NH2), 0.18 (s, 9H, Si(CH3)3). 13C NMR (126 MHz, CDCl3) δ 197.20 (CO), 151.24 (C—Ar), 140.72 (C—Ar), 138.19 (C—Ar), 137.94 (C—Ar), 132.27 (C—Ar), 129.59 (C—Ar), 126.48 (q, C—Ar, J=1.19), 122.13 (q, J=274.80, CF3), 117.35 (C—Ar), 117.10 (C—Ar), 110.28 (C—Ar), 104.86 (CSi(CH3)3), 92.21 (CCSi(CH3)3), 28.62 (q, J=40.69, CN2), 0.22 (Si(CH3)3). Exact Mass, 401.12. 399.7011 [M−H]−, 401.7108 [M+H]+.

Provenance & Evidence