Triethylamine → HCID 67238714, compound

Participants

Reaction Steps

To a solution of 4-(4-nitronaphthalen-1-yloxy)pyridin-2-amine (100 mg, 0.356 mmol) and Et3N (100 μL, 0.71 mmol) in dry THF was added phenyl carbonochloridate (49 μL, 0.39 mmol) and the mixture maintained at RT for 2 hr. Pyrrolidine (88 μL, 1.068 mmol) was added and after 16 h at RT the resulting mixture was partitioned between aq NH4Cl (10 mL) and DCM (10 mL). The aq layer was separated and extracted with DCM (3×10 mL) and the combined organic extracts were dried (MgSO4) and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 40 g, EtOAc in isohexane, 0-100%, gradient elution) to afford N-(4-(4-nitronaphthalen-1-yloxy)pyridin-2-yl)pyrrolidine-1-carboxamide, Intermediate K2, as a yellow solid (110 mg, 79%); Rt 1.84 min (Method 2); m/z 379 (M+H)+ (ES+).

Provenance & Evidence