Potassium Carbonate → HCID 66672822, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl-2(5-(2-bromo-4-oxofuro[3,2-c]pyridine-5(4H)-yl)1H-indazol-1-yl)acetate (0.77 g, 19 mmol) in DMSO (44 mL) was added 4-chlorophenyl boronic acid (0.32 g, 2.1 mmol), K2CO3 (0.52 g, 3.8 mmol) and bis(triphenylphosphine)palladium (II) chloride (0.13 g, 0.19 mmol). The solution was evacuated for 15 minutes under high vacuum then backfilled with argon. The process was repeated three times. The reaction mixture was stirred at 90° C. for 2 h; then the reaction mixture was diluted with H2O (20 mL) and extracted with CH2Cl2 (3×40 mL). The extracts were washed with brine (2×50 mL), dried (Na2SO4), filtered and concentrated. Purification by flash chromatography (silica gel, CH2Cl2/MTBE, 100:0 to 1:1) yielded the title compound (0.38 mg, 46%) as a light yellow solid: 1H NMR (300 MHz, CDCl3) δ 8.12 (s, 1H), 7.77-7.63 (m, 4H), 7.53-7.41 (m, 4H), 7.35 (d, J=7.5 Hz, 1H), 6.68 (dd, J=7.5, 0.9 Hz, 1H), 5.22 (s, 2H), 3.78 (s, 3H); ESI MS m/z 434 [M+H]+.

Provenance & Evidence