2-fluoro-5-iodo-N-methylbenzamide

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

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Add bis(triphenylphosphine)palladium (II) dichloride (64 mg, 0.091 mmol), copper (I) iodide (35 mg, 0.19 mmol), and 3-ethynyl-5-methoxypyridine, (prepared as described in PREPARATION 10), (250 mg, 1.9 mmol) to a solution of 2-fluoro-5-iodo-N-methylbenzamide, (prepared as described in PREPARATION 39), (0.63 g, 2.3 mmol) in triethylamine (3.8 mL, 27.3 mmol) and heat at 60° C. for 16 h. Cool to room temperature and concentrate. Purify by silica gel chromatography, eluting with 100:0 to 10:90 dichloromethane:ethyl acetate, followed by a second silica gel chromatography eluting with 50:50 to 75:25 ethyl acetate:hexanes, to give the title compound as a white solid (390 mg, 73%). Cool to room temperature concentrate Purify by silica gel chromatography eluting with 100:0 to 10:90 dichloromethane eluting with 50:50 to 75:25 ethyl acetate

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Add bis(triphenylphosphine)palladium (II) dichloride (45 mg, 0.06 mmol), copper (I) iodide (26 mg, 0.14 mmol), and 3-chloro-5-ethynylpyridine, (prepared as described in PREPARATION 27), (200 mg, 1.45 mmol) to a solution of 2-fluoro-5-iodo-N-methylbenzamide, (prepared as described in PREPARATION 39), (0.39 g, 1.39 mmol) in triethylamine (6 mL, 43 mmol) and heat at 70° C. After 10 min, add toluene (10 mL) to the solidified reaction mixture and heat at 70° C. for 1 h. Concentrate and purify using silica gel chromatography, eluting with 40:60 ethyl acetate:hexanes, to give the title compound as a white solid (300 mg, 72%). heat at 70° C. for 1 h Concentrate purify eluting with 40:60 ethyl acetate

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Add bis(triphenylphosphine)palladium (II) dichloride (45 mg, 0.06 mmol), copper (I) iodide (26 mg, 0.14 mmol), and 3-chloro-5-ethynylpyridine, (prepared as described in PREPARATION 27), (200 mg, 1.45 mmol) to a solution of 2-fluoro-5-iodo-N-methylbenzamide, (prepared as described in PREPARATION 39), (0.39 g, 1.39 mmol) in triethylamine (6 mL, 43 mmol) and heat at 70° C. After 10 min, add toluene (10 mL) to the solidified reaction mixture and heat at 70° C. for 1 h. Concentrate and purify using silica gel chromatography, eluting with 40:60 ethyl acetate:hexanes, to give the title compound as a white solid (300 mg, 72%). heat at 70° C. for 1 h Concentrate purify eluting with 40:60 ethyl acetate

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

Procedure: Add methylamine hydrochloride (0.57 g, 8.4 mmol) and triethylamine (2.17 mL, 15.5 mmol) to a solution of 2-fluoro-5-iodobenzoyl chloride (2.0 g, 7.0 mmol) in dichloromethane (100 mL) at 0° C. Warm to room temperature and stir 20 h. Concentrate and purify by silica gel chromatography, eluting with a gradient of 75:25 to 60:40 hexanes:ethyl acetate, to give the title compound as a white solid (1.7 g, 87%). Concentrate purify by silica gel chromatography eluting with a gradient of 75:25 to 60:40 hexanes

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Add bis(triphenylphosphine)palladium (II) dichloride (64 mg, 0.091 mmol), copper (I) iodide (35 mg, 0.19 mmol), and 3-ethynyl-5-methoxypyridine, (prepared as described in PREPARATION 10), (250 mg, 1.9 mmol) to a solution of 2-fluoro-5-iodo-N-methylbenzamide, (prepared as described in PREPARATION 39), (0.63 g, 2.3 mmol) in triethylamine (3.8 mL, 27.3 mmol) and heat at 60° C. for 16 h. Cool to room temperature and concentrate. Purify by silica gel chromatography, eluting with 100:0 to 10:90 dichloromethane:ethyl acetate, followed by a second silica gel chromatography eluting with 50:50 to 75:25 ethyl acetate:hexanes, to give the title compound as a white solid (390 mg, 73%). Cool to room temperature concentrate Purify by silica gel chromatography eluting with 100:0 to 10:90 dichloromethane eluting with 50:50 to 75:25 ethyl acetate

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Add bis(triphenylphosphine)palladium (II) dichloride (45 mg, 0.06 mmol), copper (I) iodide (26 mg, 0.14 mmol), and 3-chloro-5-ethynylpyridine, (prepared as described in PREPARATION 27), (200 mg, 1.45 mmol) to a solution of 2-fluoro-5-iodo-N-methylbenzamide, (prepared as described in PREPARATION 39), (0.39 g, 1.39 mmol) in triethylamine (6 mL, 43 mmol) and heat at 70° C. After 10 min, add toluene (10 mL) to the solidified reaction mixture and heat at 70° C. for 1 h. Concentrate and purify using silica gel chromatography, eluting with 40:60 ethyl acetate:hexanes, to give the title compound as a white solid (300 mg, 72%). heat at 70° C. for 1 h Concentrate purify eluting with 40:60 ethyl acetate

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

Procedure: Add methylamine hydrochloride (0.57 g, 8.4 mmol) and triethylamine (2.17 mL, 15.5 mmol) to a solution of 2-fluoro-5-iodobenzoyl chloride (2.0 g, 7.0 mmol) in dichloromethane (100 mL) at 0° C. Warm to room temperature and stir 20 h. Concentrate and purify by silica gel chromatography, eluting with a gradient of 75:25 to 60:40 hexanes:ethyl acetate, to give the title compound as a white solid (1.7 g, 87%). Concentrate purify by silica gel chromatography eluting with a gradient of 75:25 to 60:40 hexanes