4,7-Dibromofuro[3,2-c]pyridine → 7-Bromofuro[3,2-c]pyridine

Participants

Reaction Conditions

Reaction Steps

A suspension of 4,7-dibromofuro[3,2-c]pyridine (3.50 g, 12.6 mmol), HCO2Na (2.59 g, 38.1 mmol) and Pd(PPh3)4 (360 mg, 0.32 mmol) in dry DMF (35 mL) was heated at 100° C. (bath temperature) under Ar for 9 h. LC-MS showed the reaction was almost complete. The mixture was diluted with water (50 mL) and EtOAc (200 mL). Layers were separated and the organic phase was washed with water (3×40 mL), brine (40 mL), and dried over Na2SO4. The solvent was removed and residue was purified by silica gel chromatography eluting with Hexanes-EtOAc (80:20→70:30) to provide the title compound as an off-white solid (1.92 g, 77%). 1H NMR (CDCl3, 400 MHz): δ=6.98 (d, J=2.3 Hz, 1H), 7.79 (d, J=2.3 Hz, 1H), 8.62 (s, 1H), 8.89 (s, 1H).

Provenance & Evidence