Bicarbonate Ion → HCID 135610094, compound

Participants

Reaction Steps

To a solution of 6-bromo-3H-quinazolin-4-one (38.9 mg, 0.1728 mmol) dissolved in 2 ml N,N-dimethylacetamide in a 20 ml vial, 2-chloro-6-methoxy-phenylboronic acid (128.88 mg, 0.6914 mmol) dissolved in 1 ml ethanol and potassium carbonate (26.28 mg, 0.19 mmol) dissolved in 1 ml water were added. Triphenylphosphine (4.5 mg, 0.017 mmol) and tris(dibenzylideneacetone)dipalladium(0) (3.2 mg, 3.5 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. 3.4 mg product was obtained. Yield: 24.3%; 1H NMR (500 MHz, DMSO-d6): δ 3.70812(s, 3H), 7.13816–7.15637 (dd, J1=7.945 Hz, J2=0.32 Hz, 1H), 7.18430–7.20184 (dd, J1=7.85 Hz, J2=0.92 Hz 1H), 7.40806–7.44074 (dd, J1=8.205 Hz, J2=8.135 Hz, 1H), 7.66531–7.68611 (dd, J1=8.305 Hz, J2=2.04 Hz, 1H), 7.71531–7.73209 (d, J=8.39 Hz, 1H), 7.92946–7.93334 (d, J=1.94 Hz, 1H), 8.16800 (s, 1H); ESI-MS: m/z 287 (M++1)

Provenance & Evidence