4-Tert-Butylaniline → HCID 11472986, compound

Participants

Reaction Steps

The product from Example 1A (570 mg, 2.86 mmol) in SOCl2 (10 mL) was refluxed for 1 hour. The solution was allowed to cool to room temperature and SOCl2 was removed under reduced pressure. The residue was taken up in tetrahydrofuran (10 mL) and treated with DIEA (2.5 mL, 14.4 mmol, 5 eq) and 4tert-butylaniline (0.41 mL, 2.57 mmol). After stirring overnight at room temperature, the tetrahydrofuran was removed under reduced pressure and replaced with ethyl acetate (20 mL). The ethyl acetate was washed with H2O and brine, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was chromatographed on silica gel (eluant gradient from 7:3 hexanes:ethyl acetate to 1:1 hexanes:ethyl acetate) to provide the title compound as a solid. 1H NMR (300 MHz, DMSO-d6) δ 10.26 (s, 1H), 8.71–8.74 (m, 1H), 8.23–8.26 (m, 2H), 8.07–8.10 (m, 3H), 7.94 (td, j=7.4 Hz, 2.1 Hz, 1H), 7.70–7.73 (m, 2H), 7.37–7.44 (m, 3H), 1.29 (s, 9H); MS (ESI+) m/z 331 (M+H)+.

Provenance & Evidence