Hydrochloric Acid → HCID 178465847, compound

Participants

Reaction Steps

Following a procedure for Stille coupling on aromatic compounds (Kosugi, M. et al., Bull. Chem. Soc. Jpn. 1987, 60, 767-768), a mixture of 6 (75 mg, 0.12 mmol), 7 (80 μL, 0.24 mmol) and (PPh3)2PdCl2 (9.0 mg, 0.013 mmol) was refluxed in THF (12 mL) for 20 h in a Schlenk line. The reaction mixture was treated with 10% aqueous HCl (4 mL) at room temperature for 2 h. CH2Cl2 was added and the organic layer was separated. The organic layer was washed with saturated aqueous NaHCO3, water, and brine. The organic layer was dried (Na2SO4), concentrated and chromatographed [silica, CH2Cl2/hexanes (1:1)], affording a purple solid (50 mg, 71%): 1H NMR δ-0.98 (brs, 2H), 1.86 (s, 6H), 2.02 (s, 6H), 2.61 (s, 3H), 2.66 (s, 3H), 3.05 (s, 3H), 4.56 (s, 2H), 7.24 (s, 2H), 7.50 (d, J=7.8 Hz, 2H), 7.96 (d, J=7.8 Hz, 2H), 8.23 (d, J=4.4 Hz, 1H), 8.31 (d, J=4.4 Hz, 1H), 8.68 (d, J=4.4 Hz, 1H), 8.69 (s, 1H), 8.70 (d, J=4.4 Hz, 1H), 8.86 (s, 1H), 9.98 (s, 1H); LD-MS obsd 590.8; FAB-MS obsd 590.3052, calcd 590.3046 (C40H38N4O); λabs 422, 661 (logs ε=4.67) nm, λem 668, 711, 714 nm (Φf=0.23).

Provenance & Evidence