[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[N:7][CH:8]=2)[CH:3]=[CH:2]1.C[Mg]I.[C:13](Cl)(=[O:17])[C:14](Cl)=[O:15].[N:19]1C=CC=CC=1.N>CCOCC.[Cl-].[Zn+2].[Cl-]>[O:15]=[C:14]([C:3]1[C:4]2[C:9](=[CH:8][N:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1)[C:13]([NH2:19])=[O:17]A solution of 6-azaindole (1.0 eq.) in ether is treated with methyl magnesium iodide (1.1 eq.) at room temperature, stirred for 1 h, treated with zinc chloride (1.2 eq), stirred for a further 1 h, treated with oxalyl chloride (10 eq.), stirred for 10 h and concentrated in vacuo to remove the solvent and excess oxalyl chloride. The resultant residue is dissolved in CH3CN and pyridine (1.6 eq.), treated with ammonia (2 eq., solution in dioxane), stirred for 1 h and concentrated in vacuo. This residue is purified by chromatography [silica gel, CH2Cl2/methanol (containing 5% ammonium hydroxide) as eluent] to afford the title acetamide compound.
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