1H-indole-2-carbaldehyde

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

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

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

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

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

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

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

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

Procedure: In a 100-mL round-bottom flask, a total of 1.9 g (13 mmol) of 2-formylindole and 780 mg (26 mmol) of NaH (80% dispersion in mineral oil) was stirred in 150 mL of dry THF under N2 at 0° C. (ice bath). At total of 3.39 g (15.7 mmol) of dimethylvinylsulfonium iodide was added after 20 minutes, and then the reaction mixture was stirred overnight (about 15 hours). A total of 3.38 g of NaN3 (50 mmol) in 20 mL of 1:1 acetone:water was added to the reaction mixture, and then the reaction mixture was stirred at room temperature for about 12 hours. The mixture was evaporated under reduced pressure, and then purified by flash chromatography (3:2 petroleum ether:ethyl acetate). A yellow oil (2.0 g) was obtained (72%). 1H NMR (CDCl3): δ2.42 (d, 1H, J=5.5), 3.96 (dd, 1H, J=2.5, J2 =11), 4.39 (dd, 1H, J1 =5.5, J2 =11), 4.76 (m, 1H), 4.84 (br s, 1H), 6.56 (s, 1H), 7.10-7.39 (m, 3H), 7.65 (d, 1H, J=7.5). 13C NMR (CDCl3 (CDCl3): δ50.2, 64.6, 79.8, 96.4, 109.7, 119.8, 121.5, 122.1, 131.9, 132.9, 137.1. the reaction mixture was stirred at room temperature for about 12 hours The mixture was evaporated under reduced pressure purified by flash chromatography (3:2 petroleum ether:ethyl acetate)

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

Procedure: In a 100-mL round-bottom flask, a total of 1.9 g (13 mmol) of 2-formylindole and 780 mg (26 mmol) of NaH (80% dispersion in mineral oil) was stirred in 150 mL of dry THF under N2 at 0° C. (ice bath). At total of 3.39 g (15.7 mmol) of dimethylvinylsulfonium iodide was added after 20 minutes, and then the reaction mixture was stirred overnight (about 15 hours). A total of 3.38 g of NaN3 (50 mmol) in 20 mL of 1:1 acetone:water was added to the reaction mixture, and then the reaction mixture was stirred at room temperature for about 12 hours. The mixture was evaporated under reduced pressure, and then purified by flash chromatography (3:2 petroleum ether:ethyl acetate). A yellow oil (2.0 g) was obtained (72%). 1H NMR (CDCl3): δ2.42 (d, 1H, J=5.5), 3.96 (dd, 1H, J=2.5, J2 =11), 4.39 (dd, 1H, J1 =5.5, J2 =11), 4.76 (m, 1H), 4.84 (br s, 1H), 6.56 (s, 1H), 7.10-7.39 (m, 3H), 7.65 (d, 1H, J=7.5). 13C NMR (CDCl3 (CDCl3): δ50.2, 64.6, 79.8, 96.4, 109.7, 119.8, 121.5, 122.1, 131.9, 132.9, 137.1. the reaction mixture was stirred at room temperature for about 12 hours The mixture was evaporated under reduced pressure purified by flash chromatography (3:2 petroleum ether:ethyl acetate)

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

Procedure: In a 100-mL round-bottom flask, a total of 626 mg (4.31 mmol) of 2-formylindole and 259 mg (8.63 mmol) of NaH (80% dispersion in mineral oil) was stirred in 50 mL of dry THF under N2 at 0° C. ice bath). A total of 935 mg (4.31 mmol) of dimethylvinylsulfonium iodide was added after 20 minutes and the reaction mixture was stirred overnight (about 15 hours). The mixture was then evaporated under reduced pressure and the residue was washed with pentane or hexane. The filtrate was evaporated under reduced pressure. The resulting solid was analyzed by GC-MS and had a purity of 99%. Yield: 665 mg (72%). 1H NMR (CDCl3): δ4.09 (dd, 1H, J1 =12), 4.33 (d, 1H, J=12), 4.40 (d, 1H, J=2.5), 4.50 (t, 1H, J=2.5), 6.59 (s, 1H), 0.0-7.3 (m, 3H), 7.60 (d, 1H, J=7.5), 13C NMR (CDCl3 : δ45.94, 51.35, 60.83, 97.62, 109.23, 119.64, 121.68, 122.34, 131.44, 133.90, 139.12, MS (EI): m/z 171 (M+). The mixture was then evaporated under reduced pressure the residue was washed with pentane or hexane The filtrate was evaporated under reduced pressure

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

Procedure: In a 100-mL round-bottom flask, a total of 626 mg (4.31 mmol) of 2-formylindole and 259 mg (8.63 mmol) of NaH (80% dispersion in mineral oil) was stirred in 50 mL of dry THF under N2 at 0° C. ice bath). A total of 935 mg (4.31 mmol) of dimethylvinylsulfonium iodide was added after 20 minutes and the reaction mixture was stirred overnight (about 15 hours). The mixture was then evaporated under reduced pressure and the residue was washed with pentane or hexane. The filtrate was evaporated under reduced pressure. The resulting solid was analyzed by GC-MS and had a purity of 99%. Yield: 665 mg (72%). 1H NMR (CDCl3): δ4.09 (dd, 1H, J1 =12), 4.33 (d, 1H, J=12), 4.40 (d, 1H, J=2.5), 4.50 (t, 1H, J=2.5), 6.59 (s, 1H), 0.0-7.3 (m, 3H), 7.60 (d, 1H, J=7.5), 13C NMR (CDCl3 : δ45.94, 51.35, 60.83, 97.62, 109.23, 119.64, 121.68, 122.34, 131.44, 133.90, 139.12, MS (EI): m/z 171 (M+). The mixture was then evaporated under reduced pressure the residue was washed with pentane or hexane The filtrate was evaporated under reduced pressure

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

Procedure: A total of 1.76 g of 2-indolemethanol was dissolved in dry CH2Cl2 (20 mL) at room temperature and stirred overnight with MnO2 (2.1 g, 24 mmol). The mixture was filtered through Celite, the filtrate was evaporated under reduced pressure, and the product was purified by flash chromatography (CH2Cl2). Yield: 1.31 g (75%), 1H NMR (CDCl3): δ7.1-7.5 (m, 4H), 7.76 (d, 1H, J=7.8 Hz), 9.41 (br s, 1H), 9.86 (s, 1H).MS EI): m/z 145 (M+). The mixture was filtered through Celite the filtrate was evaporated under reduced pressure the product was purified by flash chromatography (CH2Cl2)