2-fluoro-5-iodo-N,N-dimethylbenzamide

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

Procedure: Add bis(triphenylphosphine)palladium (II) dichloride (46 mg, 0.07 mmol), copper (I) iodide (25 mg, 0.13 mmol), and 3-chloro-5-ethynylpyridine, (prepared as described in PREPARATION 27), (200 mg, 1.45 μmmol) to a solution of 2-fluoro-5-iodo-N,N-dimethylbenzamide, (prepared as described in PREPARATION 45), (0.600 g, 2.1 mmol) in triethylamine (4.3 mL, 31 mmol) and place in an oil bath at 70° C. Add toluene (10 mL) and heat for 2 h. Concentrate and purify by silica gel chromatography, eluting with 50:50 ethyl acetate:hexanes, to give the free base of the title compound as a colorless oil. Dissolve the free base in diethyl ether (50 mL) and add 2 M hydrogen chloride in diethyl ether (2.6 mL, 5.2 mmol). Stir for 10 min, concentrate, triturate with diethyl ether and dry to give the title compound as a light yellow solid (350 mg, >99%). Concentrate purify by silica gel chromatography eluting with 50:50 ethyl acetate

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

Procedure: Add bis(triphenylphosphine)palladium (II) dichloride (46 mg, 0.07 mmol), copper (I) iodide (25 mg, 0.13 mmol), and 3-chloro-5-ethynylpyridine, (prepared as described in PREPARATION 27), (200 mg, 1.45 μmmol) to a solution of 2-fluoro-5-iodo-N,N-dimethylbenzamide, (prepared as described in PREPARATION 45), (0.600 g, 2.1 mmol) in triethylamine (4.3 mL, 31 mmol) and place in an oil bath at 70° C. Add toluene (10 mL) and heat for 2 h. Concentrate and purify by silica gel chromatography, eluting with 50:50 ethyl acetate:hexanes, to give the free base of the title compound as a colorless oil. Dissolve the free base in diethyl ether (50 mL) and add 2 M hydrogen chloride in diethyl ether (2.6 mL, 5.2 mmol). Stir for 10 min, concentrate, triturate with diethyl ether and dry to give the title compound as a light yellow solid (350 mg, >99%). Concentrate purify by silica gel chromatography eluting with 50:50 ethyl acetate

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

Procedure: Add a 2.0 M solution of dimethylamine in tetrahydrofuran (5 mL, 10.1 mmol) to a solution of 2-fluoro-5-iodobenzoylchloride (1.3 g, 4.6 mmol) in dichloromethane (20 mL) and stir at room temperature for 0.5 h. Sequentially wash the reaction mixture with a 1 N hydrochloric acid (50 mL), a 1 N sodium hydroxide (50 mL), and an aqueous saturated solution of sodium chloride (50 mL). Dry (sodium sulfate), filter, and concentrate to give the title compound as a white solid (1.3 g, 98%). Sequentially wash the reaction mixture with a 1 N hydrochloric acid (50 mL) Dry (sodium sulfate) filter concentrate

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

Procedure: Add bis(triphenylphosphine)palladium (II) dichloride (46 mg, 0.07 mmol), copper (I) iodide (25 mg, 0.13 mmol), and 3-chloro-5-ethynylpyridine, (prepared as described in PREPARATION 27), (200 mg, 1.45 μmmol) to a solution of 2-fluoro-5-iodo-N,N-dimethylbenzamide, (prepared as described in PREPARATION 45), (0.600 g, 2.1 mmol) in triethylamine (4.3 mL, 31 mmol) and place in an oil bath at 70° C. Add toluene (10 mL) and heat for 2 h. Concentrate and purify by silica gel chromatography, eluting with 50:50 ethyl acetate:hexanes, to give the free base of the title compound as a colorless oil. Dissolve the free base in diethyl ether (50 mL) and add 2 M hydrogen chloride in diethyl ether (2.6 mL, 5.2 mmol). Stir for 10 min, concentrate, triturate with diethyl ether and dry to give the title compound as a light yellow solid (350 mg, >99%). Concentrate purify by silica gel chromatography eluting with 50:50 ethyl acetate

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

Procedure: Add a 2.0 M solution of dimethylamine in tetrahydrofuran (5 mL, 10.1 mmol) to a solution of 2-fluoro-5-iodobenzoylchloride (1.3 g, 4.6 mmol) in dichloromethane (20 mL) and stir at room temperature for 0.5 h. Sequentially wash the reaction mixture with a 1 N hydrochloric acid (50 mL), a 1 N sodium hydroxide (50 mL), and an aqueous saturated solution of sodium chloride (50 mL). Dry (sodium sulfate), filter, and concentrate to give the title compound as a white solid (1.3 g, 98%). Sequentially wash the reaction mixture with a 1 N hydrochloric acid (50 mL) Dry (sodium sulfate) filter concentrate