Sodium Hydroxide → 5-(2-Phenoxy-phenyl)-3-phenyl-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of azaindole 28 (1.16 g, 2.31 mmol) in EtOH (70 mL) was added a 10% sodium hydroxide solution (8.5 mL), and the mixture was heated at 105° C. After 1 h, the mixture was allowed to cool to r.t. and partitioned between chloroform and saturated brine. The aqueous layer was extracted with chloroform (3×), and the combined organic extracts dried (MgSO4), filtered and concentrated. The residue was purified by silicagel chromatography (gradient elution, hexanes to 5% EtOAc in dichloromethane) to afford a yellow solid which was washed with cold Et2O to furnish azaindole 29 (0.546 g, 65%) as a cream coloured solid. 1H NMR (400 MHz; CDCl3) δ6.95-6.98 (m, 2H), 7.04 (tt, J=7.4, 1.0 Hz, 1H), 7.11 (dd, J=8.1, 1.2 Hz, 1H), 7.25-7.31 (m, 4H), 7.35-7.41 (m, 3H), 7.54-7.57 (m, 4H), 8.41 (d, J=2.0 Hz, 1H), 8.58 (d, J=2.0 Hz, 1H), 10.78 (bs, 1H).

Provenance & Evidence