Bicarbonate Ion → HCID 18455729, compound

Participants

Reaction Steps

To a solution of 6-Bromo-3-(3-hydroxy-propionyl)-3H-quinazolin-4-one (9.8 mg, 0.033 mmol) dissolved in 1 ml N,N-dimethylacetamide in a 20 ml vial, 2,6-dimethylphenyl boronic acid (9.89 mg, 0.066 mmol) dissolved in 0.5 ml ethanol and potassium carbonate (5 mg, 0.036 mmol) dissolved in 0.5 ml water were added. Triphenylphosphine (0.87 mg, 3.3 umol) and tris(dibenzylideneacetone)dipalladium(0) (0.6 mg, 0.6 umol) were added to the mixture which refluxed overnight. The crude product was poured into 5 ml saturated bicarbonate solution and methylene chloride was used to extract the product. Solvent in the organic phase was removed under vacuum. The resulted residue was purified by preparative HPLC. 5.2 mg product was obtained. Yield: 49%; 1H NMR (500 MHz, DMSO-d6): δ 1.96247(s, 6H), 2.76290–2.79002(t, J=6.805 Hz, 2H), ), 4.15954–4.18664 (t, J=6.785 Hz, 2H), 7.14682–7.7.1621(d, J=7.64 Hz, 1H), 7.19338–7.21062(dd, J1=8.62 Hz, J2=6.41 Hz, 1H), 7.60532–7.62604(dd, J1=8.365 Hz, J2=2.03 Hz, 1H), 7.75204–7.76861 (d, J=8.285 Hz, 1H), 7.84928–7.85312(d, J=1.92 Hz, 1H), 8.41195(s, 1H); ESI-MS: m/z 323 (M++1)

Provenance & Evidence