C([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:17][C:18]([O:20]C)=O)[CH:9]=1)C1C=CC=CC=1.[CH2:22]([Mg]Cl)[CH:23]([CH3:25])[CH3:24].CCOCC>C1COCC1>[CH3:22][CH:23]([CH3:25])[CH2:24][C:18](=[O:20])[CH2:17][N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:9]1To a solution of methyl indol-1-ylacetate (1.13 g, 5.9 mmol) from Example 1, Step 1, in THF at -78° C. was added dropwise a solution of 2M isobutyl magnesium chloride in Et2O (3.3 mL, 6.6 mmol). The reaction mixture was warmed up to 0° C. and kept at this temperature until the starting material disappeared. The reaction mixture was quenched with a 0.5M solution of Na and K tartrate and extracted with EtOAc. The extract was washed with a solution of NH4OAc, dried over MgSO4 and evaporated to dryness. The crude residue was chromatographed on flash silica gel column eluting with EtOAc-hexane (1:9) to afford the pure title product.
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