Ethanol → HCID 87168273, compound

Participants

Reaction Steps

To a solution of Na2CO3 (0.70 g, 6.6 mmol) in H2O (5 mL) was added indole-5-boronic acid (1.0 g, 6.2 mmol) and EtOH (25 mL). After stirring at rt for 30 min, 3,6-dichloropyridazine (935 mg, 6.30 mmol), toluene (50 mL) and Pd(PPh3)4 (0.30 g) were added. The mixture was stirred at 90° C. for 30 h and then evaporated in vacuo. The residue was treated with CH2Cl2 (100 mL), washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography, eluting with (CH2Cl2-MeOH=100:5) to give 0.35 g (37% yield) of the product as a yellow solid. 1H NMR (DMSO-d6) δ 6.52 (1H, s), 7.40 (1H, s), 7.50 (1H, d, 6.3 Hz), 7.86-7.90 (2H, m), 8.27 (1H, d, 6.9 Hz), 8.32 (1H, s), 11.32 (1H, s). MS m/e 230 (M+H+); Calculated MW: 229 for C12H8ClN5.

Provenance & Evidence