Methyl iodide → 2-Methyl-5-(2-phenoxy-phenyl)-3-phenyl-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Steps

To a stirred and cooled (−78° C.) solution of the azaindole 28 (80 mg, 0.16 mmol) in dry THF (2 mL) was added a 1.5 M solution of tert-butyllithium in pentane (0.13 mL, 0.19 mmol) dropwise. After 0.6 h, methyl iodide (0.10 mL, 1.61 mmol) was added dropwise and the reaction mixture allowed to slowly warm to room temperature. Following a further 22.5 h the mixture was diluted with EtOAc and saturated NaHCO3 solution and partitioned. The aqueous layer was washed with EtOAc (3×). The combined organic extracts were dried (MgSO4), filtered and concentrated. The product was purified by PTLC using hexanes-EtOAc=4:1 as eluent to afford the desired azaindole 63 (4.4 mg, 7.3%). 1H NMR (400 MHz; CDCl3) δ 3.94 (s, 3H), 6.93-6.96 (m, 2H), 7.01-7.05 (m, 1H), 7.08 (dd, J=1.3 and 8.1 Hz, 1H), 7.22-7.29 (m, 3H), 7.33-7.39 (m, 4H), 7.50-7.54 (m, 3H), 8.35 (d, J=2.0 Hz, 1H) and 8.57 (d, J=2.0 Hz, 1H). MS (CI) m/z 377 (MH+).

Provenance & Evidence