Iodoethane → 1-Benzenesulfonyl-2-ethyl-5-(3-fluoro-phenyl)-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Steps

1.7 M solution of t-BuLi in pentane (0.71 mL, 1.20 mmol) was added dropwise to a stirred and cooled (−78° C.) solution of 12 (352.0 mg, 1.00 mmol) in THF (2.0 mL). The mixture turned red-brown. After the addition, the mixture was stirred for 30 min at −78° C. Neat EtI (150 μL, 1.88 mol) was added in one portion, and the mixture was allowed to reach 0° C. over a period of 1 h 15 min. The reaction was quenched by the addition of saturated aqueous NaHCO3 solution. The mixture was then extracted with AcOEt (3×3 mL). Combined organic solutions were washed with brine, dried (MgSO4), concentrated and purified by SGC with hexane:AcOEt as eluent in gradient to afford 13 (138.5 mg, 36%) as white solid. 1H NMR (400 MHz, CDCl3) δ 1.42 (t, J=7.3 Hz, 3H), 3.21 (qd, J=7.3, 1.2 Hz, 2H), 6.39 (t, J=1.2 Hz, 1H), 7.07 (dddd, J=8.4, 8.0, 2.5, 1.0 Hz, 1H), 7.25 (ddd, J=9.9, 2.5, 1.7 Hz, 1H), 7.34 (ddd, J=7.7, 1.7, 1.0 Hz, 1H), 7.42 (ddd, J=8.0, 7.7, 5.9 Hz, 1H), 7.46-7.51 (m, 2H), 7.54-7.60 (m, 1H), 7.86 (d, J=2.2 Hz, 1H), 8.15-8.19 (m, 2H), 8.57 (d, J=2.2 Hz, 1H).

Provenance & Evidence