Triethylamine → HCID 18939012, compound

Participants

Reaction Steps

To a solution of 42 mg (0.124 mmol) 2-phenyl-3-(4-pyridyl)-5-[(4-carboxy)phenyl]-1H-pyrrole (prepared according to Example 51) in 800 uL DMF was added 1.5 equivalents BOP reagent (benzotriazol-1-yloxy-tris-(dimethylamino)phosphonium hexafluorophosphate), 1.2 equivalents 2-(aminomethyl)pyridine, and 2.5 equivalents triethylamine. The mixture was stirred at room temperature for 15 hours. The reaction was quenched by the addition of 5% NaHCO3 solution and ethyl acetate (EtOAc). After separation of phases, the aqueous phase was re-extracted with EtOAc. The combined organic layers were washed with 5% NaHCO3 solution, water, brine, and dried over Na2SO4. After filtration and concentration of the filtrate in vacuo, the crude product was flash chromatographed (gradient elution with 1.0%-5.0% MeOH/CH2Cl2) to the desired product as a cream-colored solid, homogeneous by TLC. FAB ms: Calc.: 430 for C28 H22N4O; Obs.: 431 (M+ +1).

Provenance & Evidence