5-methyl-1-(3-methylbutyl)indole-2,3-dione

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: This compound was made in a similar manner to 1-butyl-3-hydroxy-3-(2-oxo-2-(pyridin-2-yl)ethyl)indolin-2-one using 1-isopentyl-5-methylindoline-2,3-dione and commercially available 1-(1H-indol-3-yl)ethanone (purchased from Fisher Scientific). 1H-NMR δ 9.21 (bs, NH), 8.34 (m, 1H), 7.67 (d, 1H), 7.38 (m, 1H), 7.30-7.23 (m, 3H), 7.08 (d, 1H), 6.73 (d, 1H) 5.74 (bs, 1H), 3.68 (t, 2H), 3.49 (d, 1H), 3.21 (d, 1H), 2.27 (s, 3H), 1.67-1.49 (m, 3H), 0.95 (dd, 6H).

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a flame dried flask cooled under argon was added freshly prepared LDA (0.82 mL, 0.48 mmol, 0.38M in anhydrous THF). While stirring at −78° C., 3-bromo-2-methylpyridine (50 μL, 0.48 mmol, purchased from Aldrich) was added. The solution stirred at this temperature for two hours at which point a 1-isopentyl-5-methylindoline-2,3-dione (0.045 grams, 0.19 mmol, 0.4 M in THF) was added. The solution was then warmed to room temperature slowly. Once all of the starting material had been consumed, the reaction was quenched with ammonium chloride (saturated), diluted with ethyl acetate, and the organic layer removed. The aqueous layer was salted out using sodium chloride and washed two more times with ethyl acetate. The combined organic material was dried with sodium sulfate, filtered, and concentrated. Purification was done on preparative thin layer chromatography using hexanes/ethyl acetate (2:1) to afford the desired material. (8% Yield). 1H NMR δ 8.53 (dd, 1H), 7.89 (dd, 1H), 7.17-7.09 (m, 3H), 7.03 (d, 1H), 6.73 (d, 1H), 3.83-57 (m, 2H), 3.52 (d, 1H), 3.34 (d, 1H), 2.30 (s, 3H), 1.65 (m, 1H), 1.54 (m, 2H), 0.96 (dd, 6H). Calculated mass for C20H23BrN2O2 402.09, observed, 425.1 (M+Na). To a flame dried flask cooled under argon was added The solution was then warmed to room temperature slowly Once all of the starting material had been consumed the reaction was quenched with ammonium chloride (saturated) diluted with ethyl acetate the organic layer removed washed two more times with ethyl acetate The combined organic material was dried with sodium sulfate filtered concentrated Purification

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Was made in an analogous fashion to 1-ethyl-5-methyl-2-oxoindolin-3-yl benzoate using 1-isopentyl-5-methylindoline-2,3-dione. 1H NMR δ 8.12 (d, 2H), 7.58 (t, 1H), 7.45 (t, 2H), 7.25 (s, 1H), 7.16 (d, 1H), 6.77 (d, 1H), 6.15 (s, 1H), 3.75 (m, 2H), 2.30 (s, 3H), 1.70 (m, 1H), 1.59 (m, 2H), 1.00 (d, 6H).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Made in an analogous fashion to 1-propylindoline-2,3-dione using commercially available 5-methyl isatin (purchased from Fisher Scientific) and 1-bromo-3-methylbutane (purchased from Fisher Scientific). 1H NMR δ 7.41 (m, 2H), 6.78 (d, 1H), 3.71 (t, 2H), 2.33 (s, 3H), 1.57 (m, 3H), 0.99 (d, 6H).