4-bromo-2-methyl-1-oxidopyridin-1-ium

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

Procedure: 4-Nitro-2-picoline N-oxide (1.0 g, 6.5 mmol) was treated with acetyl bromide (3.5 mL, 47 mmol) as described in Example 65b to provide the title compound (0.38 g, 31%) as an orange-brown oil.

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

Procedure: 4-Nitro-2-picoline N-oxide (1.0 g, 6.5 mmol) was treated with acetyl bromide (3.5 mL, 47 mmol) as described in Example 65b to provide the title compound (0.38 g, 31%) as an orange-brown oil.

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

Procedure: To a solution of 4-bromo-2-methylpyridine-1-oxide (4.00 g, 21.40 mmol) in DCM (20 mL) is added acetic anhydride (6 mL). The mixture is stirred at room temperature for 1 hour and then heated at reflux overnight. The solvent is removed under vacuum and the crude product is filtered through a silica plug, eluting with DCM to afford the title compound as an orange oil (815 mg). heated at reflux overnight The solvent is removed under vacuum the crude product is filtered through a silica plug eluting with DCM

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

Procedure: To a solution of 4-bromo-2-methylpyridine-1-oxide (4.00 g, 21.40 mmol) in DCM (20 mL) is added acetic anhydride (6 mL). The mixture is stirred at room temperature for 1 hour and then heated at reflux overnight. The solvent is removed under vacuum and the crude product is filtered through a silica plug, eluting with DCM to afford the title compound as an orange oil (815 mg). heated at reflux overnight The solvent is removed under vacuum the crude product is filtered through a silica plug eluting with DCM

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

Procedure: A solution of 4-bromo-2-methylpyridine (5 g, 29 mmol) in DCM (20 mL) is cooled to 0° C. and m-CPBA (7.55 g, 43.87 mmol, 1.5 equiv.) is added portionwise over 30 min. The ice bath is then removed and the mixture is allowed to stir at room temperature for 3 hours. The resulting solution is diluted with sodium bicarbonate (sat. aq.) and extracted with DCM. The organic layers are combined, washed with sodium bicarbonate (sat. aq.), dried over Na2SO4, and concentrated under vacuum to afford the title compound as a pale orange oil which is without further purification. The ice bath is then removed The resulting solution is diluted with sodium bicarbonate (sat. aq.) extracted with DCM washed with sodium bicarbonate (sat. aq.) dried over Na2SO4 concentrated under vacuum

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

Procedure: To a solution of 4-bromo-2-methylpyridine-1-oxide (4.00 g, 21.40 mmol) in DCM (20 mL) is added acetic anhydride (6 mL). The mixture is stirred at room temperature for 1 hour and then heated at reflux overnight. The solvent is removed under vacuum and the crude product is filtered through a silica plug, eluting with DCM to afford the title compound as an orange oil (815 mg). heated at reflux overnight The solvent is removed under vacuum the crude product is filtered through a silica plug eluting with DCM

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

Procedure: A solution of 4-bromo-2-methylpyridine (5 g, 29 mmol) in DCM (20 mL) is cooled to 0° C. and m-CPBA (7.55 g, 43.87 mmol, 1.5 equiv.) is added portionwise over 30 min. The ice bath is then removed and the mixture is allowed to stir at room temperature for 3 hours. The resulting solution is diluted with sodium bicarbonate (sat. aq.) and extracted with DCM. The organic layers are combined, washed with sodium bicarbonate (sat. aq.), dried over Na2SO4, and concentrated under vacuum to afford the title compound as a pale orange oil which is without further purification. The ice bath is then removed The resulting solution is diluted with sodium bicarbonate (sat. aq.) extracted with DCM washed with sodium bicarbonate (sat. aq.) dried over Na2SO4 concentrated under vacuum

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

Procedure: 4-Nitro-2-picoline N-oxide (1.0 g, 6.5 mmol) was treated with acetyl bromide (3.5 mL, 47 mmol) as described in Example 65b to provide the title compound (0.38 g, 31%) as an orange-brown oil.

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

Procedure: To a solution of 4-bromo-2-methylpyridine-1-oxide (4.00 g, 21.40 mmol) in DCM (20 mL) is added acetic anhydride (6 mL). The mixture is stirred at room temperature for 1 hour and then heated at reflux overnight. The solvent is removed under vacuum and the crude product is filtered through a silica plug, eluting with DCM to afford the title compound as an orange oil (815 mg). heated at reflux overnight The solvent is removed under vacuum the crude product is filtered through a silica plug eluting with DCM

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

Procedure: A solution of 4-bromo-2-methylpyridine (5 g, 29 mmol) in DCM (20 mL) is cooled to 0° C. and m-CPBA (7.55 g, 43.87 mmol, 1.5 equiv.) is added portionwise over 30 min. The ice bath is then removed and the mixture is allowed to stir at room temperature for 3 hours. The resulting solution is diluted with sodium bicarbonate (sat. aq.) and extracted with DCM. The organic layers are combined, washed with sodium bicarbonate (sat. aq.), dried over Na2SO4, and concentrated under vacuum to afford the title compound as a pale orange oil which is without further purification. The ice bath is then removed The resulting solution is diluted with sodium bicarbonate (sat. aq.) extracted with DCM washed with sodium bicarbonate (sat. aq.) dried over Na2SO4 concentrated under vacuum