N-(2-fluoro-4-iodophenyl)acetamide

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A suspension of N-(2-fluoro-4-iodo-phenyl)-acetamide (5 g, 18.24 mmol) in acetonitrile (100 mL) was cooled to 0° C. and then treated with sodium azide (3.56 g, 54.7 mmol). The reaction mixture was then treated with trifluoromethanesulfonic anhydride (13.6 g, 48 mmol). The resulting reaction mixture was allowed to warm to 25° C. where it was stirred overnight, at which time, thin layer chromatography analysis of the reaction mixture indicated the absence of starting material. The reaction mixture was then concentrated in vacuo. The resulting residue was diluted with ethyl acetate (100 mL) and water (100 mL). The two layers were separated, and the aqueous layer was extracted with ethyl acetate (1×50 mL). The combined organic extracts were washed with a saturated aqueous sodium chloride solution (1×100 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40M, Silica, 4/1 hexanes/ethyl acetate) afforded 1-(2-fluoro-4-iodo-phenyl)-5-methyl-1H-tetrazole (3.45 g, 62%) as a white solid: mp 122-124° C.; EI-HRMS m/e calcd for C8H6FIN4 (M+) 303.9621, found 303.9615. The resulting reaction mixture to warm to 25° C. where it The reaction mixture was then concentrated in vacuo The resulting residue was diluted with ethyl acetate (100 mL) and water (100 mL) The two layers were separated the aqueous layer was extracted with ethyl acetate (1×50 mL) The combined organic extracts were washed with a saturated aqueous sodium chloride solution (1×100 mL) dried over anhydrous magnesium sulfate filtered concentrated in vacuo

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A suspension of N-(2-fluoro-4-iodo-phenyl)-acetamide (5 g, 18.24 mmol) in acetonitrile (100 mL) was cooled to 0° C. and then treated with sodium azide (3.56 g, 54.7 mmol). The reaction mixture was then treated with trifluoromethanesulfonic anhydride (13.6 g, 48 mmol). The resulting reaction mixture was allowed to warm to 25° C. where it was stirred overnight, at which time, thin layer chromatography analysis of the reaction mixture indicated the absence of starting material. The reaction mixture was then concentrated in vacuo. The resulting residue was diluted with ethyl acetate (100 mL) and water (100 mL). The two layers were separated, and the aqueous layer was extracted with ethyl acetate (1×50 mL). The combined organic extracts were washed with a saturated aqueous sodium chloride solution (1×100 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40M, Silica, 4/1 hexanes/ethyl acetate) afforded 1-(2-fluoro-4-iodo-phenyl)-5-methyl-1H-tetrazole (3.45 g, 62%) as a white solid: mp 122-124° C.; EI-HRMS m/e calcd for C8H6FIN4 (M+) 303.9621, found 303.9615. The resulting reaction mixture to warm to 25° C. where it The reaction mixture was then concentrated in vacuo The resulting residue was diluted with ethyl acetate (100 mL) and water (100 mL) The two layers were separated the aqueous layer was extracted with ethyl acetate (1×50 mL) The combined organic extracts were washed with a saturated aqueous sodium chloride solution (1×100 mL) dried over anhydrous magnesium sulfate filtered concentrated in vacuo

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 2-fluoro-4-iodoaniline (4.74 g, 20 mmol) in dry tetrahydrofuran (20 mL) was cooled to 0° C. and then treated with acetic anhydride (8.2 g, 80 mmol). The reaction mixture was stirred for 10 min at 0° C. and then was allowed to warm to 25° C. where it was stirred for 2 h. After this time, thin layer chromatography analysis of the reaction mixture indicated the absence of starting material. The reaction mixture was then concentrated in vacuo to afford a crude residue. The residue precipitated from diethyl ether (50 mL) and hexanes (50 mL). The solid was collected by filtration and washed with hexanes to afford N-(2-fluoro-4-iodo-phenyl)-acetamide (5.12 g, 92%) as a white crystalline solid: mp 152-154° C.; EI-HRMS m/e calcd for C8H7FINO (M+) 278.9556, found 278.9559. to warm to 25° C. where it was stirred for 2 h The reaction mixture was then concentrated in vacuo to afford a crude residue The residue precipitated from diethyl ether (50 mL) and hexanes (50 mL) The solid was collected by filtration washed with hexanes

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A suspension of N-(2-fluoro-4-iodo-phenyl)-acetamide (5.00 g, 18.24 mmol) in acetonitrile (100 mL) was cooled to 0° C. and then treated with sodium azide (3.56 g, 54.7 mmol). The reaction mixture was then treated with trifluoromethanesulfonic anhydride (13.6 g, 48 mmol). The resulting reaction mixture was allowed to warm to 25° C. where it was stirred overnight, at which time, thin layer chromatography analysis of the reaction mixture indicated the absence of starting material. The reaction mixture was then concentrated in vacuo. The resulting residue was diluted with ethyl acetate (100 mL) and water (100 mL). The two layers were separated, and the aqueous layer was extracted with ethyl acetate (1×50 mL). The combined organic extracts were washed with a saturated aqueous sodium chloride solution (1×100 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40M, Silica, 4/1 hexanes/ethyl acetate) afforded 1-(2-fluoro-4-iodo-phenyl)-5-methyl-1H-tetrazole (3.45 g, 62%) as a white solid: mp 122-124° C.; EI-HRMS m/e calcd for C8H6FIN4 (M+) 303.9621, found 303.9615. The resulting reaction mixture to warm to 25° C. where it The reaction mixture was then concentrated in vacuo The resulting residue was diluted with ethyl acetate (100 mL) and water (100 mL) The two layers were separated the aqueous layer was extracted with ethyl acetate (1×50 mL) The combined organic extracts were washed with a saturated aqueous sodium chloride solution (1×100 mL) dried over anhydrous magnesium sulfate filtered concentrated in vacuo

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A suspension of N-(2-fluoro-4-iodo-phenyl)-acetamide (5.00 g, 18.24 mmol) in acetonitrile (100 mL) was cooled to 0° C. and then treated with sodium azide (3.56 g, 54.7 mmol). The reaction mixture was then treated with trifluoromethanesulfonic anhydride (13.6 g, 48 mmol). The resulting reaction mixture was allowed to warm to 25° C. where it was stirred overnight, at which time, thin layer chromatography analysis of the reaction mixture indicated the absence of starting material. The reaction mixture was then concentrated in vacuo. The resulting residue was diluted with ethyl acetate (100 mL) and water (100 mL). The two layers were separated, and the aqueous layer was extracted with ethyl acetate (1×50 mL). The combined organic extracts were washed with a saturated aqueous sodium chloride solution (1×100 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40M, Silica, 4/1 hexanes/ethyl acetate) afforded 1-(2-fluoro-4-iodo-phenyl)-5-methyl-1H-tetrazole (3.45 g, 62%) as a white solid: mp 122-124° C.; EI-HRMS m/e calcd for C8H6FIN4 (M+) 303.9621, found 303.9615. The resulting reaction mixture to warm to 25° C. where it The reaction mixture was then concentrated in vacuo The resulting residue was diluted with ethyl acetate (100 mL) and water (100 mL) The two layers were separated the aqueous layer was extracted with ethyl acetate (1×50 mL) The combined organic extracts were washed with a saturated aqueous sodium chloride solution (1×100 mL) dried over anhydrous magnesium sulfate filtered concentrated in vacuo

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 2-fluoro-4-iodoaniline (4.74 g, 20 mmol) in dry tetrahydrofuran (20 mL) was cooled to 0° C. and then treated with acetic anhydride (8.2 g, 80 mmol). The reaction mixture was stirred for 10 min at 0° C. and then was allowed to warm to 25° C. where it was stirred for 2 h. After this time, thin layer chromatography analysis of the reaction mixture indicated the absence of starting material. The reaction mixture was then concentrated in vacuo to afford a crude residue. The residue precipitated from diethyl ether (50 mL) and hexanes (50 mL). The solid was collected by filtration and washed with hexanes to afford N-(2-fluoro-4-iodo-phenyl)-acetamide (5.12 g, 92%) as a white crystalline solid: mp 152-154° C.; EI-HRMS m/e calcd for C8H7FINO (M+) 278.9556, found 278.9559. to warm to 25° C. where it was stirred for 2 h The reaction mixture was then concentrated in vacuo to afford a crude residue The residue precipitated from diethyl ether (50 mL) and hexanes (50 mL) The solid was collected by filtration washed with hexanes

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A suspension of N-(2-fluoro-4-iodo-phenyl)-acetamide (5.00 g, 18.24 mmol) in acetonitrile (100 mL) was cooled to 0° C. and then treated with sodium azide (3.56 g, 54.7 mmol). The reaction mixture was then treated with trifluoromethanesulfonic anhydride (13.6 g, 48 mmol). The resulting reaction mixture was allowed to warm to 25° C. where it was stirred overnight, at which time, thin layer chromatography analysis of the reaction mixture indicated the absence of starting material. The reaction mixture was then concentrated in vacuo. The resulting residue was diluted with ethyl acetate (100 mL) and water (100 mL). The two layers were separated, and the aqueous layer was extracted with ethyl acetate (1×50 mL). The combined organic extracts were washed with a saturated aqueous sodium chloride solution (1×100 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40M, Silica, 4/1 hexanes/ethyl acetate) afforded 1-(2-fluoro-4-iodo-phenyl)-5-methyl-1H-tetrazole (3.45 g, 62%) as a white solid: mp 122-124° C.; EI-HRMS m/e calcd for C8H6FIN4 (M+) 303.9621, found 303.9615. The resulting reaction mixture to warm to 25° C. where it The reaction mixture was then concentrated in vacuo The resulting residue was diluted with ethyl acetate (100 mL) and water (100 mL) The two layers were separated the aqueous layer was extracted with ethyl acetate (1×50 mL) The combined organic extracts were washed with a saturated aqueous sodium chloride solution (1×100 mL) dried over anhydrous magnesium sulfate filtered concentrated in vacuo

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 2-fluoro-4-iodoaniline (4.74 g, 20 mmol) in dry tetrahydrofuran (20 mL) was cooled to 0° C. and then treated with acetic anhydride (8.2 g, 80 mmol). The reaction mixture was stirred for 10 min at 0° C. and then was allowed to warm to 25° C. where it was stirred for 2 h. After this time, thin layer chromatography analysis of the reaction mixture indicated the absence of starting material. The reaction mixture was then concentrated in vacuo to afford a crude residue. The residue precipitated from diethyl ether (50 mL) and hexanes (50 mL). The solid was collected by filtration and washed with hexanes to afford N-(2-fluoro-4-iodo-phenyl)-acetamide (5.12 g, 92%) as a white crystalline solid: mp 152-154° C.; EI-HRMS m/e calcd for C8H7FINO (M+) 278.9556, found 278.9559. to warm to 25° C. where it was stirred for 2 h The reaction mixture was then concentrated in vacuo to afford a crude residue The residue precipitated from diethyl ether (50 mL) and hexanes (50 mL) The solid was collected by filtration washed with hexanes

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 2-fluoro-4-iodoaniline (4.74 g, 20 mmol) in dry tetrahydrofuran (20 mL) was cooled to 0° C. and then treated with acetic anhydride (8.2 g, 80 mmol). The reaction mixture was stirred for 10 min at 0° C. and then was allowed to warm to 25° C. where it was stirred for 2 h. After this time, thin layer chromatography analysis of the reaction mixture indicated the absence of starting material. The reaction mixture was then concentrated in vacuo to afford a crude residue. The residue precipitated from diethyl ether (50 mL) and hexanes (50 mL). The solid was collected by filtration and washed with hexanes to afford N-(2-fluoro-4-iodo-phenyl)-acetamide (5.12 g, 92%) as a white crystalline solid: mp 152-154° C.; EI-HRMS m/e calcd for C8H7FINO (M+) 278.9556, found 278.9559. to warm to 25° C. where it was stirred for 2 h The reaction mixture was then concentrated in vacuo to afford a crude residue The residue precipitated from diethyl ether (50 mL) and hexanes (50 mL) The solid was collected by filtration washed with hexanes

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A suspension of N-(2-fluoro-4-iodo-phenyl)-acetamide (5 g, 18.24 mmol) in acetonitrile (100 mL) was cooled to 0° C. and then treated with sodium azide (3.56 g, 54.7 mmol). The reaction mixture was then treated with trifluoromethanesulfonic anhydride (13.6 g, 48 mmol). The resulting reaction mixture was allowed to warm to 25° C. where it was stirred overnight, at which time, thin layer chromatography analysis of the reaction mixture indicated the absence of starting material. The reaction mixture was then concentrated in vacuo. The resulting residue was diluted with ethyl acetate (100 mL) and water (100 mL). The two layers were separated, and the aqueous layer was extracted with ethyl acetate (1×50 mL). The combined organic extracts were washed with a saturated aqueous sodium chloride solution (1×100 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40M, Silica, 4/1 hexanes/ethyl acetate) afforded 1-(2-fluoro-4-iodo-phenyl)-5-methyl-1H-tetrazole (3.45 g, 62%) as a white solid: mp 122-124° C.; EI-HRMS m/e calcd for C8H6FIN4 (M+) 303.9621, found 303.9615. The resulting reaction mixture to warm to 25° C. where it The reaction mixture was then concentrated in vacuo The resulting residue was diluted with ethyl acetate (100 mL) and water (100 mL) The two layers were separated the aqueous layer was extracted with ethyl acetate (1×50 mL) The combined organic extracts were washed with a saturated aqueous sodium chloride solution (1×100 mL) dried over anhydrous magnesium sulfate filtered concentrated in vacuo