[Cl:1][C:2]1[N:7]=C2N[C:9](=O)[CH2:10][C:5]2=[CH:4][CH:3]=1.[CH3:12]C(C)([O-])C.[K+].CI.O.[CH3:21][N:22]([CH:24]=[O:25])[CH3:23]>>[Cl:1][C:2]1[N:7]=[C:21]2[N:22]([CH3:23])[C:24](=[O:25])[C:10]([CH3:9])([CH3:12])[C:5]2=[CH:4][CH:3]=1A solution of 0.25 g (1.5 mmol) 6-chloro-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one (WO9910349 A1) was dissolved in 5 ml of DMF and cooled to 5° C. To this solution was added 4.5 ml (4.5 mmol) of potassium t-butoxide (1M solution in THF) followed by 0.37 ml (6.0 mmol) of methyl iodide. The reaction mixture was stirred at 5° C. for 1 hour. The reaction mixture was poured into 50 ml of water and extracted with ethyl acetate. The ethyl acetate extract was dried (Na2SO4) and evaporated to yield 0.25 g of 6-chloro-1,3,3-trimethyl-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one as a dark amorphous solid. TLC: Rf=0.8 (1:1 hexane/ethyl acetate). 1H NMR (CDCl3) δ 7.38 (d, 1H), 6.95 (d, 1H), 3.25 (s, 3H), 1.38 (s, 3H). Mass spectrum: m/e=211,213 (p+1, p+3).
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