ethyl 4-oxohexanoate

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

Procedure: A mixture of 1-(4-fluorophenyl)hydrazine hydrochloride (1.03 g), ethyl 4-oxo-hexanoate (1.0 g), 2-propanol (25 ml) and H2SO4 is refluxed under nitrogen for 9 hours. After cooling the mixture is poured into a aqueous solution of NaHCO3, extracted with AcOEt and evaporated to dryness to yield 1.45 g of isopropyl 5-fluoro-3-methyl-1H-indole-2-propanoate. is refluxed under nitrogen for 9 hours After cooling the mixture extracted with AcOEt evaporated to dryness

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

Procedure: A mixture of 1-(4-fluorophenyl)hydrazine hydrochloride (1.03 g), ethyl 4-oxo-hexanoate (1.0 g), 2-propanol (25 ml) and H2SO4 is refluxed under nitrogen for 9 hours. After cooling the mixture is poured into a aqueous solution of NaHCO3, extracted with AcOEt and evaporated to dryness to yield 1.45 g of isopropyl 5-fluoro-3-methyl-1H-indole-2-propanoate. is refluxed under nitrogen for 9 hours After cooling the mixture extracted with AcOEt evaporated to dryness

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (2-amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)(p-tolyl)methanone (0.542 g; 2 mmol) and ethyl 4-oxohexanoate (0.348 g; 2.2 mmol) in dry DMF (8 mL) under a nitrogen atmosphere was added chlorotrimethylsilane (1.02 mL; 8 mmol) dropwise. The mixture was stirred in a sealed tube and heated at 100° C. for 24 h. After cooling to room temperature, the reaction mixture was partitioned between ethyl acetate and water. The organic phase was successively washed with a saturated solution of sodium hydrogen carbonate, water, brine, dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel column using a gradient of ethyl acetate (1-30%) in heptane to afford 0.508 g (64%) of the title compound as a yellow oil. After cooling to room temperature the reaction mixture was partitioned between ethyl acetate and water The organic phase was successively washed with a saturated solution of sodium hydrogen carbonate, water, brine dried over sodium sulphate filtered concentrated under reduced pressure The residue was purified by flash chromatography on silica gel column

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

Procedure: A mixture of 1-(4-fluorophenyl)hydrazine hydrochloride (1.03 g), ethyl 4-oxo-hexanoate (1.0 g), 2-propanol (25 ml) and H2SO4 is refluxed under nitrogen for 9 hours. After cooling the mixture is poured into a aqueous solution of NaHCO3, extracted with AcOEt and evaporated to dryness to yield 1.45 g of isopropyl 5-fluoro-3-methyl-1H-indole-2-propanoate. is refluxed under nitrogen for 9 hours After cooling the mixture extracted with AcOEt evaporated to dryness