(4-bromo-1-oxo-2,3-dihydroinden-5-yl) trifluoromethanesulfonate

反応条件: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Trifluoro-methanesulfonic acid 4-bromo-1-oxo-indan-5-yl ester (10.30 g, 28.68 mmol) is stirred in 50 mL of dry N,N-dimethylformamide under argon atmosphere. Zinc cyanide (1.01 g, 8.60 mmol), 1,1-bis(diphenylphosphino) ferrocene (1.58 g, 2.86 mmol) and tris(dibenzylideneacetone)dipalladium(0) (1.32 g, 1.44 mmol) are added the reaction mixture is warmed at 70° C. for 1 h. The reaction mixture is partioned between ethyl acetate and water, the organic phase is washed with brine, washed with water, dried over sodium sulfate and concentrated under vacuum. The crude product obtained is purified by flash chromatography (cyclohexane/ethyl acetate 99/01→50/50) to give the title compound (Yield: 2.2 g). the organic phase is washed with brine washed with water dried over sodium sulfate concentrated under vacuum The crude product obtained is purified by flash chromatography (cyclohexane/ethyl acetate 99/01→50/50)

反応条件: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Trifluoro-methanesulfonic acid 4-bromo-1-oxo-indan-5-yl ester (10.30 g, 28.68 mmol) is stirred in 50 mL of dry N,N-dimethylformamide under argon atmosphere. Zinc cyanide (1.01 g, 8.60 mmol), 1,1-bis(diphenylphosphino) ferrocene (1.58 g, 2.86 mmol) and tris(dibenzylideneacetone)dipalladium(0) (1.32 g, 1.44 mmol) are added the reaction mixture is warmed at 70° C. for 1 h. The reaction mixture is partioned between ethyl acetate and water, the organic phase is washed with brine, washed with water, dried over sodium sulfate and concentrated under vacuum. The crude product obtained is purified by flash chromatography (cyclohexane/ethyl acetate 99/01→50/50) to give the title compound (Yield: 2.2 g). the organic phase is washed with brine washed with water dried over sodium sulfate concentrated under vacuum The crude product obtained is purified by flash chromatography (cyclohexane/ethyl acetate 99/01→50/50)

反応条件: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Zn(CN)2 (0.60 g) and 1,1′-bis(diphenylphosphino)-ferrocene (0.92 g) are added to a solution of trifluoro-methanesulfonic acid 4-bromo-1-oxo-indan-5-yl ester (5.90 g) in N,N-dimethylformamide (30 mL) at room temperature. The mixture is purged with Ar for 5 min prior to addition of tris(dibenzylideneacetone)dipalladium(0) (760 mg). The mixture is heated to 70° C. and stirred at this temperature for 1 h. After cooling to room temperature, ethyl acetate is added and the resulting mixture is washed with water and brine. The organic phase is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→50:50) to give the title compound. LC (method 2): tR=0.88 min; Mass spectrum (ESI−): m/z=234/236 (Br) [M−H]−. The mixture is purged with Ar for 5 min to addition of tris(dibenzylideneacetone)dipalladium(0) (760 mg) After cooling to room temperature ethyl acetate is added the resulting mixture is washed with water and brine The organic phase is dried (MgSO4) concentrated The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→50:50)

反応条件: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Zn(CN)2 (0.60 g) and 1,1′-bis(diphenylphosphino)-ferrocene (0.92 g) are added to a solution of trifluoro-methanesulfonic acid 4-bromo-1-oxo-indan-5-yl ester (5.90 g) in N,N-dimethylformamide (30 mL) at room temperature. The mixture is purged with Ar for 5 min prior to addition of tris(dibenzylideneacetone)dipalladium(0) (760 mg). The mixture is heated to 70° C. and stirred at this temperature for 1 h. After cooling to room temperature, ethyl acetate is added and the resulting mixture is washed with water and brine. The organic phase is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→50:50) to give the title compound. LC (method 2): tR=0.88 min; Mass spectrum (ESI−): m/z=234/236 (Br) [M−H]−. The mixture is purged with Ar for 5 min to addition of tris(dibenzylideneacetone)dipalladium(0) (760 mg) After cooling to room temperature ethyl acetate is added the resulting mixture is washed with water and brine The organic phase is dried (MgSO4) concentrated The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→50:50)

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Trifluoromethanesulfonic anhydride (4.0 mL) is added dropwise to a solution of 4-bromo-5-hydroxy-indan-1-one (5.0 g) and 2,6-dimethylpyridine (5.1 mL) in dichloromethane (50 mL) cooled to 0° C. The cooling bath is removed and the mixture is stirred for 2 h at room temperature. The solution is partitioned between saturated aqueous NH4Cl solution and dichloromethane. The organic phase is separated, washed with brine, dried (MgSO4), and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→50:50) to give the title compound. LC (method 2): tR=1.08 min; Mass spectrum (ESI+): m/z=359/361 (Br) [M+H]+. The cooling bath is removed The solution is partitioned between saturated aqueous NH4Cl solution and dichloromethane The organic phase is separated washed with brine dried (MgSO4) concentrated The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→50:50)

反応条件: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Trifluoro-methanesulfonic acid 4-bromo-1-oxo-indan-5-yl ester (10.30 g, 28.68 mmol) is stirred in 50 mL of dry N,N-dimethylformamide under argon atmosphere. Zinc cyanide (1.01 g, 8.60 mmol), 1,1-bis(diphenylphosphino) ferrocene (1.58 g, 2.86 mmol) and tris(dibenzylideneacetone)dipalladium(0) (1.32 g, 1.44 mmol) are added the reaction mixture is warmed at 70° C. for 1 h. The reaction mixture is partioned between ethyl acetate and water, the organic phase is washed with brine, washed with water, dried over sodium sulfate and concentrated under vacuum. The crude product obtained is purified by flash chromatography (cyclohexane/ethyl acetate 99/01→50/50) to give the title compound (Yield: 2.2 g). the organic phase is washed with brine washed with water dried over sodium sulfate concentrated under vacuum The crude product obtained is purified by flash chromatography (cyclohexane/ethyl acetate 99/01→50/50)