7-chloro-6-fluoro-1H-indole

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

実験手順: A suspension of 45 mg of sodium hydride dispersion in 10 ml of tetrahydrofuran was treated with 0.2 g of 7-chloro-6-fluoroindole at 0° and stirred at this temperature for 1 hour. After the addition of 0.17 ml of (RS)-methyloxirane the reaction mixture was stirred at room temperature for 4 days and subsequently treated with water. The mixture was diluted with ether, washed with water and with saturated sodium chloride solution and the organic phase was dried over sodium sulfate. After removal of the solvent the residue was chromatographed over 15 g of silica gel with toluene-ethyl acetate (19:1). There was obtained 0.21 g (77.8%) of (RS)-1-(7-chloro-6-fluoro-indol-1-yl)-propan-2-ol as white crystals with m.p. 85°-87°. was stirred at room temperature for 4 days washed with water and with saturated sodium chloride solution the organic phase was dried over sodium sulfate After removal of the solvent the residue was chromatographed over 15 g of silica gel with toluene-ethyl acetate (19:1)

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

実験手順: A suspension of 1.92 g of an almost 1:1 mixture of 5-chloro-6-fluoro-indole-2-carboxylic acid and 7-chloro-6-fluoro-indole-2-carboxylic acid in 45 ml of diphenyl ether was stirred at 260° for 4 hours. The reaction mixture was chromatographed over 100 g of silica gel with hexane and hexane-toluene (3:1). There were obtained 0.6 g (39%) of 5-chloro-6-fluoroindole as light brown crystals with m.p. 88°-90° and 0.22 g (14%) of 7-chloro-6-fluoroindole as a dark brown oil. The reaction mixture was chromatographed over 100 g of silica gel with hexane and hexane-toluene (3:1)

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

実験手順: A suspension of 1.92 g of an almost 1:1 mixture of 5-chloro-6-fluoro-indole-2-carboxylic acid and 7-chloro-6-fluoro-indole-2-carboxylic acid in 45 ml of diphenyl ether was stirred at 260° for 4 hours. The reaction mixture was chromatographed over 100 g of silica gel with hexane and hexane-toluene (3:1). There were obtained 0.6 g (39%) of 5-chloro-6-fluoroindole as light brown crystals with m.p. 88°-90° and 0.22 g (14%) of 7-chloro-6-fluoroindole as a dark brown oil. The reaction mixture was chromatographed over 100 g of silica gel with hexane and hexane-toluene (3:1)

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

実験手順: A suspension of 1.92 g of an almost 1:1 mixture of 5-chloro-6-fluoro-indole-2-carboxylic acid and 7-chloro-6-fluoro-indole-2-carboxylic acid in 45 ml of diphenyl ether was stirred at 260° for 4 hours. The reaction mixture was chromatographed over 100 g of silica gel with hexane and hexane-toluene (3:1). There were obtained 0.6 g (39%) of 5-chloro-6-fluoroindole as light brown crystals with m.p. 88°-90° and 0.22 g (14%) of 7-chloro-6-fluoroindole as a dark brown oil. The reaction mixture was chromatographed over 100 g of silica gel with hexane and hexane-toluene (3:1)