2-(4-CHLORO-PHENYLETHYNYL)-PHENYLAMINE

General procedure: In a typical reaction, PdCl2(PPh3)2 (88 mg, 0.125 mmol), CuI (24 mg, 0.125 mmol) and THF (5 ml) were placed in an oven-dried, 2-neck RB flask. To this suspension, 2-iodoaniline (5.47 mg, 2.5 mmol) and triethylamine (702 μl, 5.0 mmol) were added. The reaction mixture was degassed by bubbling with argon for 15 min. Phenylacetylene (300 μl, 2.75 mmol) was then added, and the reaction mixture stirred at RT. After complete consumption of the 2-iodoanilines (~2 h, by TLC), the reaction mixture was filtered through celite, and the solvent rotary evaporated to obtain the crude product which was purified by silica gel (60-120 mesh) column chromatography using ethylacetate/ hexane (1:9, v/v) as eluent to give pure 2-phenylethynylaniline, 2a (400 mg, 83percent).General procedure: To a sealed tube (10 mL) was added 3-(phenylethynyl)pyridin-2-amine (1a; 50 mg, 0.26 mmol), H2O (2 mL), and AgNO3 (8.7 mg, 0.052 mmol). After ultrasonic oscillation for 5 min, the mixture was stirred at 130 C for about 16 h. The reaction product was filtered, washed with H2O, and dried to give a brown solid; yield: 48 mg (96%); mp 209-210 C; HPLC purity 98%.General procedure: In a typical reaction [Cp*IrCl2]2 (8 mg, 0.01 mmol), NaBF4 (2 mg, 0.02 mol) and 2-(phenylethynyl)aniline (97 mg, 0.5 mmol) were dissolved in dry acetonitrile (3 mL) in a Carius tube. The mixture was subjected to three cycles of freeze-pump-thaw and was then stirred at 40oC for 8 h, after which the reaction solvent was removed by rotary evaporation to give the crude product. Purification of the crude product by silica gel (60-120 mesh) column chromatography using ethylacetate/hexane (1:9, v/v) as eluent gave pure 2-phenylindole, 3a. Similar procedures were used with the other alkynylanilines to obtain 3b-s. The amount of reagents used, product formed (with yield) and HRMS for the products, are given in the Table 2.Preparation method of the above compound III-5 provided in this example:Add 227 mg (about 1 mmol) of 2-((4-chlorophenyl) ethynyl) aniline and 225 mg (about 1.5 mmol) of o-carboxybenzaldehyde to a microwave reaction tube.2 mg (about 1 mol%) of the catalyst palladium acetate and 1 mL of the solvent toluene, and then the microwave reaction tube was sealed.After stirring at 100 C for 6 hours, the solvent toluene was distilled off under reduced pressure, and purified by column chromatography using petroleum ether / ethyl acetate as an eluent.326 mg of product III-5 was obtained as a white solid with a yield of 91%.In 15 ml reaction tube adding 1 n (0.3 mmol, 68.3 mg), [RhCp * Cl2 ]2 (0.015 Mmol, 9.3 mg) and hexafluoroisopropanol (2 ml), in a nitrogen atmosphere of the reaction pipe sealing, in the 120 C stirring for 20 h. After the reaction, the reaction tube to be cooled to the room temperature, adding 10 ml water, then the extraction of ethyl acetate (10 ml × 3), after the organic phase with water and saturated salt water are successively washing, drying with anhydrous sodium sulfate. Filtering, turns on lathe does, too separating by silica gel column (petroleum ether/ethyl acetate=10/1) yellow solid product to be 2 n (53 mg, 77%). The compound of the characterization data are as follows1 m (0.3 mmol, 68.3 mg), [RhCp*Cl2] 2 (0.015 mmol, 9.3 mg) and hexafluoroisopropanol (2 mL) were sequentially added to a 15 mL reaction tube.The reaction tube was sealed in an air atmosphere, and the reaction was stirred at 120 C for 20 h. After the completion of the reaction, the reaction tube was cooled to room temperature, and 10 mL of water was added thereto, followed by extraction with ethyl acetate (10 mL × 3), and the organic phase was washed successively with water and brine, and dried over anhydrous sodium sulfate. filter, Spin dry, separated by silica gel column (petroleum ether / ethyl acetate = 5 / 1)The white solid product 2m (37 mg, 75%).

Molecular Weight:227.69
XLogP3:3.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:227.0501770
Monoisotopic Mass:227.0501770
Topological Polar Surface Area:26
Heavy Atom Count:16
Complexity:280
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes