1-(1H-indol-3-yl)ethanone

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: 3-Acetyl-1H-indole (4.00 g, 0.025 mol) was dissolved in dry THF (100 ml), and treated with 80% sodium hydride (0.794 g, 0.0263 mol) with stirring under Ar. After 0.5 h, methyl iodide (2.36 ml, 0.038 mol) was added. After 20 h, the reaction mixture was evaporated under reduced pressure and the residue partitioned between ethyl acetate and water. The organic layer was then dried (Na2SO4), and evaporated under reduced pressure to give the title compound as a pale brown oil which crystallised on standing (4.20 g, 97%). After 20 h the reaction mixture was evaporated under reduced pressure the residue partitioned between ethyl acetate and water The organic layer was then dried (Na2SO4) evaporated under reduced pressure

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

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

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

Procedure: To a solution of 41.39 g of 3-acetyl indole in 300 ml of dimethyl sulfoxide at 0° C. was added a solution of 18.6 g of potassium hydroxide in 20 ml of water. This mixture was stirred at 0° C. for 2 hours, then 47.6 ml of benzenesulfonyl chloride was added dropwise over 40 minutes. The mixture was stirred for an additional 30 mInutes, then poured into aqueous ammonium chloride and extracted several times with ether. The ether extracts were combined, washed with water, dried and evaporated, giving 59.8 g of 3-acetyl-N-phenylsulfonyl indole. The mixture was stirred for an additional 30 mInutes extracted several times with ether washed with water dried evaporated

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

Procedure: To a solution of 41.39 g of 3-acetyl indole in 300 ml of dimethyl sulfoxide at 0° C. was added a solution of 18.6 g of potassium hydroxide in 20 ml of water. This mixture was stirred at 0° C. for 2 hours, then 47.6 ml of benzenesulfonyl chloride was added dropwise over 40 minutes. The mixture was stirred for an additional 30 mInutes, then poured into aqueous ammonium chloride and extracted several times with ether. The ether extracts were combined, washed with water, dried and evaporated, giving 59.8 g of 3-acetyl-N-phenylsulfonyl indole. The mixture was stirred for an additional 30 mInutes extracted several times with ether washed with water dried evaporated

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

Procedure: 2.5 g (15.7 mmol) of 3-acetyl-1H-indole are dissolved in 100 ml of dimethylformamide, and 0.41 g (15.7 mmol) of sodium hydride and 4.0 g (16 mmol) of N-(2-bromo-ethyl)-phthalimide are added. The reaction mixture is stirred for 14 h at RT and for 3 h at 50°. 20 ml of water are added and the product is isolated by filtration. After drying at 50° under HV, N-[2-(3-acetyl-1H-indol-1-yl)-ethyl]-1H-isoindole-1,3(2H)-dione is obtained; 1H-NMR (CDCl3): 2.5 (3H,s), 4.1 (2H,t), 4.45 (2H,t), 7.2-7.9 (8H,m), 8.35 (1H n). the product is isolated by filtration After drying at 50° under HV

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

Procedure: 2.5 g (15.7 mmol) of 3-acetyl-1H-indole are dissolved in 100 ml of dimethylformamide, and 0.41 g (15.7 mmol) of sodium hydride and 4.0 g (16 mmol) of N-(2-bromo-ethyl)-phthalimide are added. The reaction mixture is stirred for 14 h at RT and for 3 h at 50°. 20 ml of water are added and the product is isolated by filtration. After drying at 50° under HV, N-[2-(3-acetyl-1H-indol-1-yl)-ethyl]-1H-isoindole-1,3(2H)-dione is obtained; 1H-NMR (CDCl3): 2.5 (3H,s), 4.1 (2H,t), 4.45 (2H,t), 7.2-7.9 (8H,m), 8.35 (1H n). the product is isolated by filtration After drying at 50° under HV

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

Procedure: Add 1.0 M t-BuOK (3.0 mL, 0.003 mol) to a stirring solution of 3-acetyl indole (0.478 g, 0.0030 mol) in dry DMF (20 mL) under N2 at ambient temperature and stir for 30 min. Add toluenesulfonyl chloride to this solution and stir the resulting mixture overnight. Pour the reaction into EtOAc—H2O, separate the organic layer and extract several times with H2O wash with brine, dry (MgSO4), filter, and evaporate on the rotary evaporator. Chromatograph on the ISCO eluting with a gradient hexane-EtOAc (0-100%) over 30 minutes to give 0.73 g (78%) of the title compound as a solid: 1H (CDCl3). δ 7.8 (d, 1H), 8.2 (s, 1H), 7.9 (d, 1H), 7.7 (d, 2H), 7.4 (m, 2H), 7.3 (d, 2H), 2.6 (s, 3H), 2.4 (s, 3H). Pour separate the organic layer extract several times with H2O wash with brine dry (MgSO4) filter evaporate on the rotary evaporator Chromatograph on the ISCO eluting with a gradient hexane-EtOAc (0-100%) over 30 minutes

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

Procedure: Add 1.0 M t-BuOK (3.0 mL, 0.003 mol) to a stirring solution of 3-acetyl indole (0.478 g, 0.0030 mol) in dry DMF (20 mL) under N2 at ambient temperature and stir for 30 min. Add toluenesulfonyl chloride to this solution and stir the resulting mixture overnight. Pour the reaction into EtOAc—H2O, separate the organic layer and extract several times with H2O wash with brine, dry (MgSO4), filter, and evaporate on the rotary evaporator. Chromatograph on the ISCO eluting with a gradient hexane-EtOAc (0-100%) over 30 minutes to give 0.73 g (78%) of the title compound as a solid: 1H (CDCl3). δ 7.8 (d, 1H), 8.2 (s, 1H), 7.9 (d, 1H), 7.7 (d, 2H), 7.4 (m, 2H), 7.3 (d, 2H), 2.6 (s, 3H), 2.4 (s, 3H). Pour separate the organic layer extract several times with H2O wash with brine dry (MgSO4) filter evaporate on the rotary evaporator Chromatograph on the ISCO eluting with a gradient hexane-EtOAc (0-100%) over 30 minutes

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

Procedure: To a stirred solution of 3-acetylindole (0.01 mol) in THF is added (BOC)2O (0.01 mol) and a tertiary amine base (0.01 mol), and the mixture is stirred. Reaction progress may be followed by TLC or HPLC. When a sufficient amount of desired product is formed, the mixture (or, optionally, the residue which is obtained after first rotary evaporating off the reaction solvent) is partitioned between ethyl acetate and an excess of about 0.1 M sodium hydroxide. The organic layer is washed with brine, dried over sodium sulfate, and rotary evaporated to give 3-acetyl-1-(tert-butoxycarbonyl)-indole, which may be purified, if needed or desired, by chromatography on silica gel or crystallization. Reaction progress