Trimethylsilyl isocyanate → HCID 11583150, compound

Participants

Reaction Steps

To a solution of 4-[{2-[(4-aminophenyl)oxy]ethyl}(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile (0.105 g, 0.25 mmol; Example 28A) in dry CH2Cl2 (5 mL) at room temp, under N2, was added TMS-isocyanate (0.05 mL, 0.29 mmol) and the mixture was stirred overnight. After 12 h, an additional portion of TMS-isocyanate (0.09 mL, 0.58 mmol) and DMAP (0.003 g, 0.025 mmol) was added and stirring continued. After 2 h, the mixture was quenched with 10% v/v HCl and the whole extracted with EtOAc (×3). Combined organics were washed (water, brine), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), followed by preparative RP-HPLC (C18 column, MeCN/water), affording 0.0448 g of the title compound as a colorless gum: MS (ES) m/z 447 (M+1).

Provenance & Evidence