2,3-Diphenylindole

General procedure: o-Halobenzaldehyde (0.25 mmol), diphenylacetylene (0.50 mmol), palladacycle (1 mol percent), additive (0.25 mmol), and K2CO3 (0.50 mmol) were dissolved in DMF (1.50 mL) in a 10 mL vial under air and heated at 100 °C for 24 h. After the reaction was complete (monitored by TLC), the mixture was diluted with CH2Cl2 (10 mL), filtered through a pad of Celite, and washed multiple times with CH2Cl2. The combined organic layer was dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure and the residue was purified by flash chromatography on silica gel (ethyl acetate/hexane) to afford the pure product.General procedure: The 25 mL RB-flask was charged with 2-haloamines (1 mmol), diphenylacetylene (1.5 mmol), LiOH·H2O (4 mmol) and catalyst (0.001 molpercent of 5 in 2 mL N, N-dimethylformamide). The reaction mixture was stirred at 130 °C for 20 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (20 mL) and washed with brine water. The combined organic phase was dried over anhydrous Na2SO4. After removal of the solvent, the residue was subjected to column chromatography on silica gel using ethyl acetate and hexane to afford the indole product in high purity. In case of 2-bromoanilines, 0.1 molpercent of catalyst 5 was applied.aryl bromide (1 mmol), alkyne (3 mmol), Na2CO3 (3 mmol), Pd/C (2 mo lpercent) and DMF (2 mL) were introduced in a sealed tube. The reactor was placed under stirring in a preheated oil bath at 120 °C or 140 °C after being flushed by argon. The reaction completion was monitored by GC. After cooling to room temperature, the reaction mixture was filtered through a celite pad, which was washed with EtOAc (100 mL). The resulting organic layer was then washed with Na2CO3 (2 .x. 40 mL) and brine (40 mL). The organic layer was dried over Na2SO4 and the solvent was removed under reduced pressure. If necessary (for the silylated compounds), the crude product could be fully deprotected by treatment with HCl 1 M before being purified by flash chromatography on silica.General procedure: The 25 mL RB-flask was charged with 2-haloamines (1 mmol), diphenylacetylene (1.5 mmol), LiOH·H2O (4 mmol) and catalyst (0.001 molpercent of 5 in 2 mL N, N-dimethylformamide). The reaction mixture was stirred at 130 °C for 20 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (20 mL) and washed with brine water. The combined organic phase was dried over anhydrous Na2SO4. After removal of the solvent, the residue was subjected to column chromatography on silica gel using ethyl acetate and hexane to afford the indole product in high purity. In case of 2-bromoanilines, 0.1 molpercent of catalyst 5 was applied.

Molecular Weight:269.3
XLogP3:5.3
Hydrogen Bond Donor Count:1
Rotatable Bond Count:2
Exact Mass:269.120449483
Monoisotopic Mass:269.120449483
Topological Polar Surface Area:15.8
Heavy Atom Count:21
Complexity:327
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes