(1S,2S)-2-(methylamino)cyclohexan-1-ol

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 443 mg (1 mmol) of 3-(2-Bromo-benzoyl)-1-(6-methyl-pyridin-2-ylmethyl)-1H-quinolin-4-one, 9.5 mg (0.05 mmol) of copper iodide, 14.2 mg (0.1 mmol) (1S,2S)-1-hydroxy-2-methylaminocyclohexane and 300 mg (2 mmol) of sodium iodide were mixed in 5 mL of dioxane. The mixture was stirred at 110° C. in a sealed tube for 18 hours. The reaction was quenched by adding 50 mL of water. The mixture was extracted with 50 mL of ethyl acetate. The organic layer was washed with 50 mL of water, 50 mL of sat. brine, dried over magnesium sulfate overnight. The solid was filtered and the filtrate was concentrated to dryness. The crude product was purified with flash chromatography to yield 270 mg of 3-(2-Iodo-benzoyl)-1-(6-methyl-pyridin-2-ylmethyl)-1H-quinolin-4-one as colorless solid. The reaction was quenched by adding 50 mL of water The mixture was extracted with 50 mL of ethyl acetate The organic layer was washed with 50 mL of water, 50 mL of sat. brine dried over magnesium sulfate overnight The solid was filtered the filtrate was concentrated to dryness The crude product was purified with flash chromatography

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 443 mg (1 mmol) of 3-(2-Bromo-benzoyl)-1-(6-methyl-pyridin-2-ylmethyl)-1H-quinolin-4-one, 9.5 mg (0.05 mmol) of copper iodide, 14.2 mg (0.1 mmol) (1S,2S)-1-hydroxy-2-methylaminocyclohexane and 300 mg (2 mmol) of sodium iodide were mixed in 5 mL of dioxane. The mixture was stirred at 110° C. in a sealed tube for 18 hours. The reaction was quenched by adding 50 mL of water. The mixture was extracted with 50 mL of ethyl acetate. The organic layer was washed with 50 mL of water, 50 mL of sat. brine, dried over magnesium sulfate overnight. The solid was filtered and the filtrate was concentrated to dryness. The crude product was purified with flash chromatography to yield 270 mg of 3-(2-Iodo-benzoyl)-1-(6-methyl-pyridin-2-ylmethyl)-1H-quinolin-4-one as colorless solid. The reaction was quenched by adding 50 mL of water The mixture was extracted with 50 mL of ethyl acetate The organic layer was washed with 50 mL of water, 50 mL of sat. brine dried over magnesium sulfate overnight The solid was filtered the filtrate was concentrated to dryness The crude product was purified with flash chromatography

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 443 mg (1 mmol) of 3-(2-Bromo-benzoyl)-1-(6-methyl-pyridin-2-ylmethyl)-1H-quinolin-4-one, 9.5 mg (0.05 mmol) of copper iodide, 14.2 mg (0.1 mmol) (1S,2S)-1-hydroxy-2-methylaminocyclohexane and 300 mg (2 mmol) of sodium iodide were mixed in 5 mL of dioxane. The mixture was stirred at 110° C. in a sealed tube for 18 hours. The reaction was quenched by adding 50 mL of water. The mixture was extracted with 50 mL of ethyl acetate. The organic layer was washed with 50 mL of water, 50 mL of sat. brine, dried over magnesium sulfate overnight. The solid was filtered and the filtrate was concentrated to dryness. The crude product was purified with flash chromatography to yield 270 mg of 3-(2-Iodo-benzoyl)-1-(6-methyl-pyridin-2-ylmethyl)-1H-quinolin-4-one as colorless solid. The reaction was quenched by adding 50 mL of water The mixture was extracted with 50 mL of ethyl acetate The organic layer was washed with 50 mL of water, 50 mL of sat. brine dried over magnesium sulfate overnight The solid was filtered the filtrate was concentrated to dryness The crude product was purified with flash chromatography