Dimethylformamide → Isoquinoline-8-carbonitrile

Participants

Reaction Steps

To a solution of 0.5035 g (2.42 mmol) 24 in 10 mL DMF was added 0.1713 g (1.45 mmol) zinc cyanide and 0.1687 g (0.15 mmol) tetrakis(triphenylphosphine)palladium(0). After 70.5 h under argon at 80° C., the reaction mixture was cooled to room temperature, diluted with 50 mL toluene and washed with 15 mL 2N NH4H. The aqueous layer was extracted with 15 mL toluene. The combined organic layers were washed with 15 mL brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography (40×105 mm silica gel, linear gradient 1-4% MeOH:CH2Cl2) yielded 25. 1H NM (CDCl3, 400 MHz) δ 9.679 (s, 1H, ArH); 8.732 (d, 1H, J=5.67 Hz, ArH); 8.097 (d, 1H, J=8.41 Hz, ArH); 8.031 (d, 1H, J=7.13, ArH); 7.771 (dd, 2H, J=6.81, 10.47 Hz, ArH); MS (Electrospray): m/z 155.0 (M+H).

Provenance & Evidence