Sodium Carbonate → HCID 67051395, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the iodide 27 (2.00 g, 3.62 mmol) in toluene (40 mL) and EtOH (40 mL) was added lithium chloride (0.46 g, 10.86 mmol), dichlorobis(triphenylphosphine) palladium (II) (0.127 g, 0.18 mmol), phenylboronic acid (0.662 g, 5.43 mmol) and 1 M sodium carbonate (9.05 mL, 9.05 mmol). The mixture was refluxed under N2 (oil bath temp. 105° C.) for 2.5 h and then concentrated in vacuo. The resulting residue was co-evaporated once from xylene and purified by silicagel chromatography (gradient elution, hexanes to dichloromethane) to afford the azaindole 28 (1.16 g, 64%) as pale yellow solid. 1H NMR (400 MHz; CDCl3) δ6.91-6.94 (m, 2H), 7.04-7.08 (m, 2H), 7.22-7.30 (m, 3H), 7.31-7.41 (m, 4H), 7.44-7.53 (m, 5H), 7.60 (tt, J=7.4, 1.3 Hz, 1H), 7.87 (s, 1H), 8.23-8.26 (m, 3H) and 8.66 (d, J=1.9 Hz, 1H).

Provenance & Evidence