Nitrogen → HCID 25139185, compound

Participants

Reaction Steps

Et4Sn (1.47 mL, 7.5 mmol) and Pd(PPh3)4 (154 mg, 0.99 mmol) were added to a N2-purged, stirred solution of iodide 133 (2.27 g, 4.97 mmol) in dry dioxane (30 mL) at 20° C. and the reaction mixture was stirred at reflux temperature under N2. After 5 h more Et4Sn (1.5 mL, 7.5 mmol) and Pd(PPh3)4 (150 mg, 0.98 mmol) were added and the mixture stirred at reflux temperature for 5 h. The mixture was cooled and partitioned between EtOAc and water. The organic layer was separated, dried and the solvent evaporated. The residue was purified by chromatography, eluting with a gradient (0-5%) of EtOAc/pet. ether, to give 1-oxide 135 (1.57 g, 88%) as a yellow solid: mp (EtOAc/pet. ether) 63-65° C.; 1H NMR δ 8.23 (s, 1H, H-9), 7.72 (s, 1H, H-5), 3.59-3.66 (m, 2H, CH2O), 3.14-3.24 (m, 2H, CH2), 2.92-3.06 (m, 4H, H-6, H-8), 2.72-2.83 (m, 1H, H-7), 1.43 (t, J=7.5 Hz, 3H, CH3), 0.87 [s, 9H, SiC(CH3)3], 0.04 [s, 6H, Si(CH3)2]. Anal. calcd for C19H29N3O2Si: C, 63.5; H, 8.1; N, 11.7. Found: C, 63.3; H, 8.2; N, 11.4%.

Provenance & Evidence