3-iodo-N-methylbenzamide

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

Procedure: To a cooled (0° C.) solution of 3-iodobenzoyl chloride (2.66 g; 10.0 mmol) in DCM (10 mL) was slowly added a 2 M solution of methylamine in THF (10 mL, 2.0 eq.). Upon completion of the addition, the ice bath was removed and the mixture was stirred overnight. All volatiles were removed in vacuo and the residue was treated with aq. NaHCO3 (25 mL) and subsequently extracted with ethyl acetate (3×15 mL). The combined organic layers were dried over MgSO4 and evaporated. The crude product was purified by column chromatography on silica gel to give the desired 3-iodo-N-methylbenzamide (0.67 g, 26% yield). Upon completion of the addition the ice bath was removed All volatiles were removed in vacuo the residue was treated with aq. NaHCO3 (25 mL) subsequently extracted with ethyl acetate (3×15 mL) The combined organic layers were dried over MgSO4 evaporated The crude product was purified by column chromatography on silica gel

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

Procedure: To a cooled (0° C.) solution of 3-iodobenzoyl chloride (2.66 g; 10.0 mmol) in DCM (10 mL) was slowly added a 2 M solution of methylamine in THF (10 mL, 2.0 eq.). Upon completion of the addition, the ice bath was removed and the mixture was stirred overnight. All volatiles were removed in vacuo and the residue was treated with aq. NaHCO3 (25 mL) and subsequently extracted with ethyl acetate (3×15 mL). The combined organic layers were dried over MgSO4 and evaporated. The crude product was purified by column chromatography on silica gel to give the desired 3-iodo-N-methylbenzamide (0.67 g, 26% yield). Upon completion of the addition the ice bath was removed All volatiles were removed in vacuo the residue was treated with aq. NaHCO3 (25 mL) subsequently extracted with ethyl acetate (3×15 mL) The combined organic layers were dried over MgSO4 evaporated The crude product was purified by column chromatography on silica gel

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

Procedure: To a cooled (0° C.) solution of 3-iodobenzoyl chloride (2.66 g; 10.0 mmol) in DCM (10 mL) was slowly added a 2 M solution of methylamine in THF (10 mL, 2.0 eq.). Upon completion of the addition, the ice bath was removed and the mixture was stirred overnight. All volatiles were removed in vacuo and the residue was treated with aq. NaHCO3 (25 mL) and subsequently extracted with ethyl acetate (3×15 mL). The combined organic layers were dried over MgSO4 and evaporated. The crude product was purified by column chromatography on silica gel to give the desired 3-iodo-N-methylbenzamide (0.67 g, 26% yield). Upon completion of the addition the ice bath was removed All volatiles were removed in vacuo the residue was treated with aq. NaHCO3 (25 mL) subsequently extracted with ethyl acetate (3×15 mL) The combined organic layers were dried over MgSO4 evaporated The crude product was purified by column chromatography on silica gel

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

Procedure: To a cooled (0° C.) solution of 3-iodobenzoyl chloride (2.66 g; 10.0 mmol) in DCM (10 mL) was slowly added a 2 M solution of methylamine in THF (10 mL, 2.0 eq.). Upon completion of the addition, the ice bath was removed and the mixture was stirred overnight. All volatiles were removed in vacuo and the residue was treated with aq. NaHCO3 (25 mL) and subsequently extracted with ethyl acetate (3×15 mL). The combined organic layers were dried over MgSO4 and evaporated. The crude product was purified by column chromatography on silica gel to give the desired 3-iodo-N-methylbenzamide (0.67 g, 26% yield). Upon completion of the addition the ice bath was removed All volatiles were removed in vacuo the residue was treated with aq. NaHCO3 (25 mL) subsequently extracted with ethyl acetate (3×15 mL) The combined organic layers were dried over MgSO4 evaporated The crude product was purified by column chromatography on silica gel

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

Procedure: To a cooled (0° C.) solution of 3-iodobenzoyl chloride (2.66 g; 10.0 mmol) in DCM (10 mL) was slowly added a 2 M solution of methylamine in THF (10 mL, 2.0 eq.). Upon completion of the addition, the ice bath was removed and the mixture was stirred overnight. All volatiles were removed in vacuo and the residue was treated with aq. NaHCO3 (25 mL) and subsequently extracted with ethyl acetate (3×15 mL). The combined organic layers were dried over MgSO4 and evaporated. The crude product was purified by column chromatography on silica gel to give the desired 3-iodo-N-methylbenzamide (0.67 g, 26% yield). Upon completion of the addition the ice bath was removed All volatiles were removed in vacuo the residue was treated with aq. NaHCO3 (25 mL) subsequently extracted with ethyl acetate (3×15 mL) The combined organic layers were dried over MgSO4 evaporated The crude product was purified by column chromatography on silica gel

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-iodobenzoic acid (1.5 g, 6 mmol) in anhydrous DMF (10 mL) was added 1,1′-carbonyldiimidazole (1.2 g, 7.2 mmol). The reaction mixture was heated to 50° C. under an atmosphere of nitrogen for 1 h. Upon cooling to room temperature, a solution of methylamine in THF (2 M, 6 mL, 10 mmol) was added. The reaction was stirred at r.t. for 15 min and then transferred into a solution of cold, saturated ammonium chloride (200 mL). The resulting precipitate was collected by filtration and dried to afford the title compound as a white solid, mp 94-97° C. Upon cooling to room temperature The resulting precipitate was collected by filtration dried

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

Procedure: To a cooled (0° C.) solution of 3-iodobenzoyl chloride (2.66 g; 10.0 mmol) in DCM (10 mL) was slowly added a 2 M solution of methylamine in THF (10 mL, 2.0 eq.). Upon completion of the addition, the ice bath was removed and the mixture was stirred overnight. All volatiles were removed in vacuo and the residue was treated with aq. NaHCO3 (25 mL) and subsequently extracted with ethyl acetate (3×15 mL). The combined organic layers were dried over MgSO4 and evaporated. The crude product was purified by column chromatography on silica gel to give the desired 3-iodo-N-methylbenzamide (0.67 g, 26% yield). Upon completion of the addition the ice bath was removed All volatiles were removed in vacuo the residue was treated with aq. NaHCO3 (25 mL) subsequently extracted with ethyl acetate (3×15 mL) The combined organic layers were dried over MgSO4 evaporated The crude product was purified by column chromatography on silica gel