Tributylphosphine → HCID 491350, compound

Participants

Reaction Steps

To a solution of the compound in Example 11 (65 mg), tributylphosphine (61 mg) and 2,4-difluorophenol (26 mg) in THF (1 ml) was added bispiperidine azodicarboxyl amide (76 mg) in THF (0.5 ml) at −45° C. under argon atmosphere, and the mixture was slowly warmed up to room temperature over 18 hoursi period. The mixture was poured into sat. NaHCO3 solution and extracted with ethyl acetate. The organic layer was washed with brine and dried over Na2SO4. After filtration, the solvent was removed under reduced pressure and the residue was chromatographed on silica gel (dichloromethane/methanol) to give a yellow oil (35 mg, 40%). ESIMS: m/z 439 (MH+); 1H-NMR (CDCl3): δ 2.07 (2H, tt, J=6.9 Hz, 5.9 Hz, CH2), 2.27 (3H, s, CH3), 2.89 (2H, t, J=6.9 Hz, NCH2), 3.83 (2H, s, NCH2), 4.13 (2H, t, J=5.9 Hz, OCH2), 5.10 (2H, s, OCH2), 6.59 (1H, d, J=7.9 Hz, Ar—H), 6.71-7.23 (6H, m, 6×Ar—H), 7.66 (1H, dd, J=1.7 Hz, 7.9 Hz, Ar—H), 8.49 (1H, d, J=4.9 Hz, Ar—H), 8.56 (1H, s, Ar—H).

Provenance & Evidence