To a solution of 7-(2-methyl-1H-indol-5-ylamino)-thieno[3,2-b]pyridine-2-carboxylic acid (0.10 g, 0.31 mmol), HATU (0.17 g, 0.46 mmol) and DMAP (0.040 g, 0.31 mmol) in DMF (3 mL) was added racemic 3-hydroxy-pyrrolidine (0.040 g, 0.46 mmol). After 3 h the reaction was quenched with a saturated aqueous solution of NaHCO3 (10 mL) and EtOAC (10 mL). The aquenched layer was further extracted with EtOAC (2×10 mL). The combined organic extracts were dried (Na2SO4) and concentrated under reduced pressure. Purification by flash chromatography on silica gel (CH2Cl2/MeOH 85:15) afforded the title compound as a yellow solid (0.093 g, 76%). MS: 393 (MH+); HPLC Rf: 3.41; HPLC purity: 87%.
