Potassium Carbonate → 2-(7-iodo-6-oxo-8-phenylpyrano[3,2-g]indazol-1(6H)-yl)acetonitrile

Participants

Reaction Steps

To a solution of 7-iodo-8-phenylpyrano[3,2-g]indazol-6(1H)-one (350 mg, 0.903 mmol) in DMF (10 mL) was added potassium carbonate (415 mg, 3 mmol) and the reaction stirred at RT. After 5 minutes, bromoacetonitrile (162 mg, 1.353 mmol) was added and the reaction stirred at RT for 2 h. The reaction mixture was partitioned between EtOAc and water. The resulting biphasic mixture was separated and the aqueous phase was extracted with EtOAc. The combined organic phase was washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 0 to 70% EtOAc in cyclohexane) to afford the title compound (116 mg, 30%), 1H NMR (500 MHz, CDCl3): δ 8.18 (br s, 1H), 8.06 (d, J=8.6 Hz, 1H), 7.90-7.88 (m, 2H), 7.75 (d, J=8.3 Hz, 1H), 7.64-7.60 (m, 3H), 5.52 (s, 2H). LCMS (Method J) RT=1.29 min, [M+H]+=428.

Provenance & Evidence