Nitrogen → HCID 25140183, compound

Participants

Reaction Conditions

Reaction Steps

Pd(OAc)2 (53 mg, 0.24 mmol) was added to a N2-purged solution of iodide 213 (1.50 g, 4.8 mmol), allyl alcohol (0.91 mL, 13.3 mmol), nBu4NBr (1.38 g, 4.3 mmol) and NaHCO3 (880 mg, 10.5 mmol) in dry DMF (40 mL) and the solution was stirred at 60° C. for 24 h under N2. The mixture was quenched with saturated aqueous NH4Cl solution (150 mL) and filtered. The filtrate was extracted with EtOAc (5×50 mL), dried and the solvent evaporated. The residue was purified by chromatography, eluting with a gradient (20-50%) of EtOAc/pet. ether, to give aldehyde 214 as a dark oil, which was crystallised from MeOH to give a pale purple solid (532 mg, 45%): mp 140-142° C.; 1H NMR δ 9.92 (s, 1H, CHO), 8.26 (t, J=1.5 Hz, 1H, H-9), 7.10 (s, 1H, H-5), 4.80 (t, J=8.4 Hz, 2H, H-7), 3.43 (dt, J=8.4, 1.5 Hz, 2H, H-8), 3.29-3.33 (m, 2H, CH2), 3.06-3.10 (m, 2H, CH2); 13C NMR δ 200.4, 166.5, 165.0, 150.3, 135.2, 129.0, 116.2, 104.0, 73.1, 40.5, 29.4, 29.0; HRMS (FAB+) calcd for C12H12N3O3 (MH+) m/z 246.0879, found 246.0881.

Provenance & Evidence