Gamma-Butyrolactone → HCID 58382148, compound

Participants

Reaction Conditions

Reaction Steps

A flask was charged with (6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanamine (0.300 g, 0.686 mmol, Preparation #I.1), dihydrofuran-2(3H)-one (0.063 mL, 0.823 mmol), 1,2,4-triazole (0.009 g, 0.13 mmol), DBU (0.021 mL, 0.13 mmol) and DCM (10 mL). The mixture was heated to about 60° C. and stirred overnight. The mixture was concentrated under reduced pressure and the residue was diluted with EtOAc (10 mL) and washed with water (10 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The material was purified by silica gel chromatography with an elution gradient of 0 to 100% EtOAc/heptane to give 4-hydroxy-N-((6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methyl)butanamide (0.150 g, 42%): LC/MS (Table 2, Method b) Rt=2.40 min; MS m/z 524 (M+H)+.

Provenance & Evidence