C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][O:8][C:9]1[CH:17]=[C:16]2[C:12]([C:13]([CH:18]=[O:19])=[CH:14][NH:15]2)=[CH:11][CH:10]=1.I[CH:21]([CH3:23])[CH3:22]>CN(C=O)C>[CH3:7][O:8][C:9]1[CH:17]=[C:16]2[C:12]([C:13]([CH:18]=[O:19])=[CH:14][N:15]2[CH:21]([CH3:23])[CH3:22])=[CH:11][CH:10]=1Cesium carbonate (577 mg, 1.77 mmol) was added to a stirred room temperature solution of 6-methoxy-1H-indole-3-carbaldehyde (104 mg, 0.590 mmol) in DMF (1.0 mL) and the mixture was stirred at room temperature for 15 minutes when 2-iodopropane (0.118 mg, 1.181 mmol) was added. The solution was stirred at 80° C. for 2 hours. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate (2×20 mL) and saturated sodium bicarbonate (5 mL), washed with brine (10 mL), dried over sodium sulfate, filtered and concentrated to give the title intermediate (120 mg).
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