Imidazole → HCID 57581112, compound

Participants

Reaction Steps

2-(4-amino-3-nitro-phenoxy)-ethanol Compound 18a (0.5 g, 2.52 mmol) was treated with TBSCl (0.42 g, 2.52 mmol) and imidazole (0.173 g, 2.52 mmol) in DMF (10 mL) at room temperature overnight. DMF was removed under vacuum and the residue was diluted with AcOEt, washed with H2O and saturated aqueous NH4Cl and dried over Na2SO4. The solvent was evaporated to dryness to provide 4-[2-(tert-butyl-dimethyl-silanyl)-ethoxy]-2-nitro-phenylamine Compound 18b (0.787 g) as a golden solid. LCMS single peak, 3.93 min, MS (ESI) m/z 313.2 (M+H+). 1H NMR (300 MHz, CDCl3) δ 7.46 (s, 1 H), 7.00 (d, 1 H, J=9.0 Hz), 6.66 (d, 1 H, J=9.0 Hz), 3.94-3.84 (m, 4 H), 0.81 (s, 9 H), −0.01 (s, 6 H).

Provenance & Evidence