Diisopropylethylamine → HCID 66744764, compound

Participants

Reaction Steps

To 1-(2-bromo-5-nitrophenyl)-N-methylmethanamine (7 g, 28.6 mmol, see WO 2008/079836 for preparation) in DMF (30 ml), was added N-(benzyloxycarbonyloxy) succinimide (8.54 g, 34.3 mmol) and N,N-diisopropylethylamine (9.98 ml, 57.1 mmol). The mixture was stirred rt for 1 h, then quenched with water, extracted with EtOAc (3×30 ml). The organic layer was washed with brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0-60% EtOAc in hexane) to yield 36A (10.66 g, 28.1 mmol, 98% yield). MS (ESI) m/z: 379.2 (M+H)+. 1H NMR (400 MHz, chloroform-d) δ ppm 7.92-8.02 (m, 2H) 7.74 (d, J=6.15 Hz, 1H) 7.33-7.42 (m, 2H) 7.28 (s, 3H) 5.22 (s, 1H) 5.15 (s, 1H) 4.61 (d, J=18.46 Hz, 2H) 3.02 (s, 3H).

Provenance & Evidence