(2-iodophenyl)hydrazine

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

Procedure: Into a dry reaction vessel, 10.3 g (44 mmol) (2-iodophenyl)hydrazine, 100 mL toluene, 50 mL triethylamine, 8.41 g (57.2 mmol) p-nitro phenylacetylene, 500 mg (Ph3P)2PdCl2, 250 mg cuprous iodide were respectively added, and reacted at 110° C. under protection of nitrogen for 4.5 h. It was cooled, rotate evaporated to dryness to remove the solvent, chromatographed on a column to obtain a red liquid 2.15 g (8.50 mmol), at a yield of 19.3%. were respectively added reacted at 110° C. under protection of nitrogen for 4.5 h It was cooled rotate evaporated to dryness to remove the solvent chromatographed on a column

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

Procedure: Into a dry reaction vessel, 10.3 g (44 mmol) (2-iodophenyl)hydrazine, 100 mL toluene, 50 mL triethylamine, 8.41 g (57.2 mmol) p-nitro phenylacetylene, 500 mg (Ph3P)2PdCl2, 250 mg cuprous iodide were respectively added, and reacted at 110° C. under protection of nitrogen for 4.5 h. It was cooled, rotate evaporated to dryness to remove the solvent, chromatographed on a column to obtain a red liquid 2.15 g (8.50 mmol), at a yield of 19.3%. were respectively added reacted at 110° C. under protection of nitrogen for 4.5 h It was cooled rotate evaporated to dryness to remove the solvent chromatographed on a column

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 21.9 g (100 mmol) o-iodophenyl amine was dissolved in 40 mL concentrated hydrochloric acid. At 0° C., 6.9 g (100 mmol) sodium nitrite (dissolved in 35 mL water) was added dropwise, and stirred at 0° C. for half an hour. Then, SnCl2.2H2O 64.7 g (300 mmol) (dissolved in 70 mL concentrated hydrochloric acid) was added dropwise slowly, and reacted for about 3 h until complete. It was filtered to obtain a white solid, washed with a saturated solution of sodium chloride, and then washed with a mixed solvent of petroleum ether and diethyl ether (1:1). Then, the solid was adjusted to be basic with sodium hydroxide solution. The solid impurity therein was filtered, the aqueous phase was extracted with dichloromethane several times, the organic phases combined, dried, rotate evaporated to dryness to obtain a colorless oil 10.3 g, at a yield of 44.0%. reacted for about 3 h until complete It was filtered to obtain a white solid washed with a saturated solution of sodium chloride washed with a mixed solvent of petroleum ether and diethyl ether (1:1) The solid impurity therein was filtered the aqueous phase was extracted with dichloromethane several times dried rotate evaporated to dryness

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

Procedure: Under argon, 200 mg (0.86 mmol) of 2-iodophenylhydrazine, 133 mg (1.11 mmol) of 2-fluoro-phenylacetylene, 30 mg (0.04 mmol) of bis(triphenylphosphine)palladium(II) chloride and 8 mg (0.04 mmol) of copper(I) iodide are introduced into a mixture of 1.5 ml of triethylamine and 3.5 ml of benzene. The mixture is heated to reflux for 4 h and then diluted with ethyl acetate and filtered. The filtrate is concentrated and the residue is purified by preparative HPLC. 36 mg (18% of theory) of the desired product are obtained. The mixture is heated to reflux for 4 h filtered The filtrate is concentrated the residue is purified by preparative HPLC

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

Procedure: Into a dry reaction vessel, 10.3 g (44 mmol) (2-iodophenyl)hydrazine, 100 mL toluene, 50 mL triethylamine, 8.41 g (57.2 mmol) p-nitro phenylacetylene, 500 mg (Ph3P)2PdCl2, 250 mg cuprous iodide were respectively added, and reacted at 110° C. under protection of nitrogen for 4.5 h. It was cooled, rotate evaporated to dryness to remove the solvent, chromatographed on a column to obtain a red liquid 2.15 g (8.50 mmol), at a yield of 19.3%. were respectively added reacted at 110° C. under protection of nitrogen for 4.5 h It was cooled rotate evaporated to dryness to remove the solvent chromatographed on a column

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 21.9 g (100 mmol) o-iodophenyl amine was dissolved in 40 mL concentrated hydrochloric acid. At 0° C., 6.9 g (100 mmol) sodium nitrite (dissolved in 35 mL water) was added dropwise, and stirred at 0° C. for half an hour. Then, SnCl2.2H2O 64.7 g (300 mmol) (dissolved in 70 mL concentrated hydrochloric acid) was added dropwise slowly, and reacted for about 3 h until complete. It was filtered to obtain a white solid, washed with a saturated solution of sodium chloride, and then washed with a mixed solvent of petroleum ether and diethyl ether (1:1). Then, the solid was adjusted to be basic with sodium hydroxide solution. The solid impurity therein was filtered, the aqueous phase was extracted with dichloromethane several times, the organic phases combined, dried, rotate evaporated to dryness to obtain a colorless oil 10.3 g, at a yield of 44.0%. reacted for about 3 h until complete It was filtered to obtain a white solid washed with a saturated solution of sodium chloride washed with a mixed solvent of petroleum ether and diethyl ether (1:1) The solid impurity therein was filtered the aqueous phase was extracted with dichloromethane several times dried rotate evaporated to dryness