Benzylamine → 5-(3-Fluoro-phenyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid benzylamide

Participants

Reaction Steps

To a solution of benzylamine (4.4 μL, 40.3 μmol) in dry CH2Cl2 (0.5 mL) was added carboxylic acid 10 (15 mg, 40.5 μmol), WSCHCl (9.32 mg, 44.86 μmol), HOBT (5.5 mg, 40.5 μmol) and i-Pr2NEt (7.1 μL, 40.8 μmol) and the reaction mixture left to stir at r.t. overnight Separation by LCMS (CombiPrep ODS-AM column) using water—acetonitrile as eluent (in gradient) afforded amide 11 (2.33 mg, 17%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 4.70 (d, J=5.5 Hz, 2H), 6.18 (t, J=5.5 Hz, 1H), 7.29-7.44 (m, 8H), 7.80 (s, 1H), 8.57 (d, J=1.8 Hz, 1H), 8.66 (d, J=2.1 Hz, 1H).

Provenance & Evidence