1-oxido-2-propan-2-ylpyridin-1-ium

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A mixture of 2-isopropylpyridine-N-oxide (104, 1.33 g, 9.7 mmol), cyanotrimethyl-silane (TMS-CN) (1.42 mL, 1.06 g, 11.0 mmol) in 1,2-dichloroethane (40 mL) was stirred at room temperature for 5 min. Then, diethylcarbamoylchloride (Et2NCOCl, 1.23 mL, 9.7 mmol) was added and the mixture was stirred at room temperature under inert atmosphere. After 2 days, a aqueous solution of potassium carbonate (10%) was added and the stirring was continued for 10 min. The organic layer was separated, and the water layer was extracted twice with 1,2-dichloroethane. The combined organic layers were washed with brine, dried (Na2SO4) and evaporated. The residue was purified by column chromatography on silica gel (Hexanes/AcOEt, 3:1) to give 1.06 g (74%) of the title compound: m/z=147 (M+H)+. the mixture was stirred at room temperature under inert atmosphere After 2 days the stirring was continued for 10 min The organic layer was separated the water layer was extracted twice with 1,2-dichloroethane The combined organic layers were washed with brine dried (Na2SO4) evaporated The residue was purified by column chromatography on silica gel (Hexanes/AcOEt, 3:1)

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

Procedure: A mixture of isopropylpyridine (2.1 g, 17.75 mmol) and m-CPBA (5.0 g, 1.3 eq.) in CH2Cl2 was stirred overnight at room temperature. Then, the reaction mixture was diluted with CH2Cl2 (twice the volume) and successively washed with aqueous sodium bicarbonate (twice) and brine, dried (Na2SO4) and evaporated to give 2.0 g (85%) of the title compound 104. successively washed with aqueous sodium bicarbonate (twice) and brine dried (Na2SO4) evaporated

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

Procedure: A mixture of 2-isopropylpyridine-N-oxide (104, 1.33 g, 9.7 mmol), cyanotrimethyl-silane (TMS-CN) (1.42 mL, 1.06 g, 11.0 mmol) in 1,2-dichloroethane (40 mL) was stirred at room temperature for 5 min. Then, diethylcarbamoylchloride (Et2NCOCl, 1.23 mL, 9.7 mmol) was added and the mixture was stirred at room temperature under inert atmosphere. After 2 days, a aqueous solution of potassium carbonate (10%) was added and the stirring was continued for 10 min. The organic layer was separated, and the water layer was extracted twice with 1,2-dichloroethane. The combined organic layers were washed with brine, dried (Na2SO4) and evaporated. The residue was purified by column chromatography on silica gel (Hexanes/AcOEt, 3:1) to give 1.06 g (74%) of the title compound: m/z=147 (M+H)+. the mixture was stirred at room temperature under inert atmosphere After 2 days the stirring was continued for 10 min The organic layer was separated the water layer was extracted twice with 1,2-dichloroethane The combined organic layers were washed with brine dried (Na2SO4) evaporated The residue was purified by column chromatography on silica gel (Hexanes/AcOEt, 3:1)

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

Procedure: A mixture of isopropylpyridine (2.1 g, 17.75 mmol) and m-CPBA (5.0 g, 1.3 eq.) in CH2Cl2 was stirred overnight at room temperature. Then, the reaction mixture was diluted with CH2Cl2 (twice the volume) and successively washed with aqueous sodium bicarbonate (twice) and brine, dried (Na2SO4) and evaporated to give 2.0 g (85%) of the title compound 104. successively washed with aqueous sodium bicarbonate (twice) and brine dried (Na2SO4) evaporated

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

Procedure: A mixture of 2-isopropylpyridine-N-oxide (104, 1.33 g, 9.7 mmol), cyanotrimethyl-silane (TMS-CN) (1.42 mL, 1.06 g, 11.0 mmol) in 1,2-dichloroethane (40 mL) was stirred at room temperature for 5 min. Then, diethylcarbamoylchloride (Et2NCOCl, 1.23 mL, 9.7 mmol) was added and the mixture was stirred at room temperature under inert atmosphere. After 2 days, a aqueous solution of potassium carbonate (10%) was added and the stirring was continued for 10 min. The organic layer was separated, and the water layer was extracted twice with 1,2-dichloroethane. The combined organic layers were washed with brine, dried (Na2SO4) and evaporated. The residue was purified by column chromatography on silica gel (Hexanes/AcOEt, 3:1) to give 1.06 g (74%) of the title compound: m/z=147 (M+H)+. the mixture was stirred at room temperature under inert atmosphere After 2 days the stirring was continued for 10 min The organic layer was separated the water layer was extracted twice with 1,2-dichloroethane The combined organic layers were washed with brine dried (Na2SO4) evaporated The residue was purified by column chromatography on silica gel (Hexanes/AcOEt, 3:1)

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

Procedure: A mixture of isopropylpyridine (2.1 g, 17.75 mmol) and m-CPBA (5.0 g, 1.3 eq.) in CH2Cl2 was stirred overnight at room temperature. Then, the reaction mixture was diluted with CH2Cl2 (twice the volume) and successively washed with aqueous sodium bicarbonate (twice) and brine, dried (Na2SO4) and evaporated to give 2.0 g (85%) of the title compound 104. successively washed with aqueous sodium bicarbonate (twice) and brine dried (Na2SO4) evaporated

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

Procedure: A mixture of 2-isopropylpyridine-N-oxide (104, 1.33 g, 9.7 mmol), cyanotrimethyl-silane (TMS-CN) (1.42 mL, 1.06 g, 11.0 mmol) in 1,2-dichloroethane (40 mL) was stirred at room temperature for 5 min. Then, diethylcarbamoylchloride (Et2NCOCl, 1.23 mL, 9.7 mmol) was added and the mixture was stirred at room temperature under inert atmosphere. After 2 days, a aqueous solution of potassium carbonate (10%) was added and the stirring was continued for 10 min. The organic layer was separated, and the water layer was extracted twice with 1,2-dichloroethane. The combined organic layers were washed with brine, dried (Na2SO4) and evaporated. The residue was purified by column chromatography on silica gel (Hexanes/AcOEt, 3:1) to give 1.06 g (74%) of the title compound: m/z=147 (M+H)+. the mixture was stirred at room temperature under inert atmosphere After 2 days the stirring was continued for 10 min The organic layer was separated the water layer was extracted twice with 1,2-dichloroethane The combined organic layers were washed with brine dried (Na2SO4) evaporated The residue was purified by column chromatography on silica gel (Hexanes/AcOEt, 3:1)

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

Procedure: A mixture of 2-isopropylpyridine-N-oxide (104, 1.33 g, 9.7 mmol), cyanotrimethyl-silane (TMS-CN) (1.42 mL, 1.06 g, 11.0 mmol) in 1,2-dichloroethane (40 mL) was stirred at room temperature for 5 min. Then, diethylcarbamoylchloride (Et2NCOCl, 1.23 mL, 9.7 mmol) was added and the mixture was stirred at room temperature under inert atmosphere. After 2 days, a aqueous solution of potassium carbonate (10%) was added and the stirring was continued for 10 min. The organic layer was separated, and the water layer was extracted twice with 1,2-dichloroethane. The combined organic layers were washed with brine, dried (Na2SO4) and evaporated. The residue was purified by column chromatography on silica gel (Hexanes/AcOEt, 3:1) to give 1.06 g (74%) of the title compound: m/z=147 (M+H)+. the mixture was stirred at room temperature under inert atmosphere After 2 days the stirring was continued for 10 min The organic layer was separated the water layer was extracted twice with 1,2-dichloroethane The combined organic layers were washed with brine dried (Na2SO4) evaporated The residue was purified by column chromatography on silica gel (Hexanes/AcOEt, 3:1)

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

Procedure: A mixture of isopropylpyridine (2.1 g, 17.75 mmol) and m-CPBA (5.0 g, 1.3 eq.) in CH2Cl2 was stirred overnight at room temperature. Then, the reaction mixture was diluted with CH2Cl2 (twice the volume) and successively washed with aqueous sodium bicarbonate (twice) and brine, dried (Na2SO4) and evaporated to give 2.0 g (85%) of the title compound 104. successively washed with aqueous sodium bicarbonate (twice) and brine dried (Na2SO4) evaporated

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

Procedure: Trimethylsilyl cyanide (1.53 mL) was added to a solution of 2-isopropylpyridine 1-oxide (example 85, step b) (1.3 g) in DCM (40 mL) and the resulting mixture was stirred for 5 min. Diethylcarbamoyl chloride (1.2 mL) was added and the mixture stirred for 3 days. An aqueous solution of potassium carbonate (10%, 40 mL) was added and the mixture stirred for 10 min. The layers were separated and the aqueous phase extracted with DCM (2×40 mL). The combined organic solutions were washed with brine (40 mL), dried over sodium sulphate, filtered and evaporated. Purification was by silica gel chromatography eluting with 3:1 isohexane:ethyl acetate. The fractions containing product were combined and evaporated to give the subtitled compound as a clear oil. Yield 1.23 g. the mixture stirred for 3 days the mixture stirred for 10 min The layers were separated the aqueous phase extracted with DCM (2×40 mL) The combined organic solutions were washed with brine (40 mL) dried over sodium sulphate filtered evaporated Purification eluting with 3:1 isohexane The fractions containing product evaporated