5-fluoro-6-methyl-1H-indole-3-carbonitrile

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 5-fluoro-6-methyl-1H-indole-3-carbonitrile (1.0 g, 5.8 mmol), cyclobutylbromide (0.81 mL, 8.6 mmol) and cesium carbonate (3.9 g, 12.1 mmol) in DMF (10 mL) was stirred at 90° C. overnight. The mixture was then poured into ice water and extracted with ethyl acetate. The organics were combined and washed with water, brine and dried over Na2SO4 and evaporated. The residue was purified by flash chromatography with 5-35% ethyl acetate in hexane to give 1-cyclobutyl-5-fluoro-6-methyl-1H-indole-3-carbonitrile (1.2 g, 92%). 1H NMR (500 MHz, CDCl3): 7.68 (1H, s), 7.35 (1H, d, J=9.6 Hz), 7.17 (1H, d, J=6.1 Hz), 4.83-4.79 (1H, m), 2.68-2.60 (2H, m), 2.48-2.37 (5H, m), 2.05-1.96 (2H, m). extracted with ethyl acetate washed with water, brine dried over Na2SO4 evaporated The residue was purified by flash chromatography with 5-35% ethyl acetate in hexane

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 5-fluoro-6-methyl-1H-indole-3-carbonitrile (1.0 g, 5.8 mmol), cyclobutylbromide (0.81 mL, 8.6 mmol) and cesium carbonate (3.9 g, 12.1 mmol) in DMF (10 mL) was stirred at 90° C. overnight. The mixture was then poured into ice water and extracted with ethyl acetate. The organics were combined and washed with water, brine and dried over Na2SO4 and evaporated. The residue was purified by flash chromatography with 5-35% ethyl acetate in hexane to give 1-cyclobutyl-5-fluoro-6-methyl-1H-indole-3-carbonitrile (1.2 g, 92%). 1H NMR (500 MHz, CDCl3): 7.68 (1H, s), 7.35 (1H, d, J=9.6 Hz), 7.17 (1H, d, J=6.1 Hz), 4.83-4.79 (1H, m), 2.68-2.60 (2H, m), 2.48-2.37 (5H, m), 2.05-1.96 (2H, m). extracted with ethyl acetate washed with water, brine dried over Na2SO4 evaporated The residue was purified by flash chromatography with 5-35% ethyl acetate in hexane

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

Procedure: Into a solution of 5-fluoro-6-methyl-1H-indole (1.9 g, 12.8 mmol) in DMF (13 mL) at −78° C. was added chlorosulfonyl isocyanate (1.33 mL, 15.3 mmol). After addition the cooling bath was removed and the mixture was allowed to warm to room temperature. The mixture was then poured into ice water, filtered and washed with water and brine. The cake was then dissolved in acetonitrile and concentrated to give 5-fluoro-6-methyl-1H-indole-3-carbonitrile (2.2 g, 100%). After addition the cooling bath was removed The mixture was then poured into ice water filtered washed with water and brine The cake was then dissolved in acetonitrile concentrated

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 5-fluoro-6-methyl-1H-indole-3-carbonitrile (1.0 g, 5.8 mmol), cyclobutylbromide (0.81 mL, 8.6 mmol) and cesium carbonate (3.9 g, 12.1 mmol) in DMF (10 mL) was stirred at 90° C. overnight. The mixture was then poured into ice water and extracted with ethyl acetate. The organics were combined and washed with water, brine and dried over Na2SO4 and evaporated. The residue was purified by flash chromatography with 5-35% ethyl acetate in hexane to give 1-cyclobutyl-5-fluoro-6-methyl-1H-indole-3-carbonitrile (1.2 g, 92%). 1H NMR (500 MHz, CDCl3): 7.68 (1H, s), 7.35 (1H, d, J=9.6 Hz), 7.17 (1H, d, J=6.1 Hz), 4.83-4.79 (1H, m), 2.68-2.60 (2H, m), 2.48-2.37 (5H, m), 2.05-1.96 (2H, m). extracted with ethyl acetate washed with water, brine dried over Na2SO4 evaporated The residue was purified by flash chromatography with 5-35% ethyl acetate in hexane

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

Procedure: Into a solution of 5-fluoro-6-methyl-1H-indole (1.9 g, 12.8 mmol) in DMF (13 mL) at −78° C. was added chlorosulfonyl isocyanate (1.33 mL, 15.3 mmol). After addition the cooling bath was removed and the mixture was allowed to warm to room temperature. The mixture was then poured into ice water, filtered and washed with water and brine. The cake was then dissolved in acetonitrile and concentrated to give 5-fluoro-6-methyl-1H-indole-3-carbonitrile (2.2 g, 100%). After addition the cooling bath was removed The mixture was then poured into ice water filtered washed with water and brine The cake was then dissolved in acetonitrile concentrated