Nitrogen → HCID 25139616, compound

Participants

Reaction Conditions

Reaction Steps

Pd(PPh3)4 (108 mg, 0.09 mmol) was added to a N2-purged, stirred solution of chloride 263 (225 mg, 0.9 mmol) and Et4Sn (0.36 mL, 1.8 mmol) in DME (15 mL) and the mixture was stirred at 85° C. for 18 h under N2. The solution was cooled to 20° C. and the solvent evaporated. The residue was purified by chromatography, eluting with a gradient (2-10%) of MeOH/DCM, to give 1-oxide 264 (130 mg, 60%) as a brown solid: mp 99-102° C.; 1H NMR δ 7.75 (d, J=8.6 Hz, 1H, H-5), 7.62 (d, J=8.6 Hz, 1H, H-6), 4.38 (s, 2H, H-10), 3.05-3.11 (m, 2H, H-7), 2.98 (q, J=7.6 Hz, 2H, CH2), 2.73 (t, J=5.9 Hz, 2H, H-8), 2.57 (s, 3H, NCH3), 1.42 (t, J=7.6 Hz, 3H, CH3); 13C NMR δ 167.1, 148.4, 137.1, 136.9, 136.3, 129.7, 126.1, 57.4, 50.5, 45.9, 30.7, 30.2, 12.2; MS (APCI) m/z (MH+, 100%). HRMS (FAB+) calcd for C13H17N4O (MH+) m/z 245.1402, found 245.1403.

Provenance & Evidence