ethyl 6-hydroxy-1H-indole-2-carboxylate

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

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

Procedure: Ethyl 6-hydroxy-1H-indole-2-carboxylate (4.6 g, 0.02 M) was heated under reflux with allylbromide (3 g, 2.2 ml, 0.025 M), K2CO3 (4.14 g 0.03 M) and acetone (150 ml) for 20 hours. On cooling the mixture was poured into brine and extracted into ethyl acetate, washed with brine, dried over magnesium sulphate and evaporated to dryness. The resulting crude brown solid was purified by extraction into hot 60°-80° petroleum ether to yield a yellow solid which was dried in vacuo, 4 g, 72%, mp 89°-91°. On cooling the mixture extracted into ethyl acetate washed with brine dried over magnesium sulphate evaporated to dryness The resulting crude brown solid was purified by extraction into hot 60°-80° petroleum ether to yield a yellow solid which was dried in vacuo, 4 g, 72%, mp 89°-91°

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

Procedure: Ethyl 6-hydroxy-1H-indole-2-carboxylate (4.6 g, 0.02 M) was heated under reflux with allylbromide (3 g, 2.2 ml, 0.025 M), K2CO3 (4.14 g 0.03 M) and acetone (150 ml) for 20 hours. On cooling the mixture was poured into brine and extracted into ethyl acetate, washed with brine, dried over magnesium sulphate and evaporated to dryness. The resulting crude brown solid was purified by extraction into hot 60°-80° petroleum ether to yield a yellow solid which was dried in vacuo, 4 g, 72%, mp 89°-91°. On cooling the mixture extracted into ethyl acetate washed with brine dried over magnesium sulphate evaporated to dryness The resulting crude brown solid was purified by extraction into hot 60°-80° petroleum ether to yield a yellow solid which was dried in vacuo, 4 g, 72%, mp 89°-91°

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

Procedure: A mixture of 1 g (4.8 mmol) ethyl-6-hydroxyindole-2-carboxylate (Journal of the American Chemical Society (1967), 89(13), 3349-50), 0.81 g (6.3 mmol) 1-isopropyl-3-pyrrolidinol, 2.83 ml (11 mmol) tri-n-butyl-phosphine and 2.56 g (9.75 mmol) 1,1′azodicarbonyl-dipiperidine in 50 ml THF was stirred at room temperature for 16 h. The suspension was filtered and the filtrated evaporated to dryness. The residue was purified with column chromatography on silica eluting with a gradient from DCM/2N NH3 in MeOH 99/1 to 19/1. The product containing fractions were combined and evaporated to dryness to yield a brown oil which was crystallized from diethyl ether and heptane to afford 0.5 g of brownish crystals (MS (m/e): 317.1 (MH+, 100%)). and after evaporation of the filtrate 0.6 g of slightly impure product which was used without further purification in the consecutive step. The suspension was filtered the filtrated evaporated to dryness The residue was purified with column chromatography on silica eluting with a gradient from DCM/2N NH3 in MeOH 99/1 to 19/1 The product containing fractions evaporated to dryness to yield a brown oil which was crystallized from diethyl ether and heptane

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

Procedure: A mixture of 1 g (4.8 mmol) ethyl-6-hydroxyindole-2-carboxylate (Journal of the American Chemical Society (1967), 89(13), 3349-50), 0.81 g (6.3 mmol) 1-isopropyl-3-pyrrolidinol, 2.83 ml (11 mmol) tri-n-butyl-phosphine and 2.56 g (9.75 mmol) 1,1′azodicarbonyl-dipiperidine in 50 ml THF was stirred at room temperature for 16 h. The suspension was filtered and the filtrated evaporated to dryness. The residue was purified with column chromatography on silica eluting with a gradient from DCM/2N NH3 in MeOH 99/1 to 19/1. The product containing fractions were combined and evaporated to dryness to yield a brown oil which was crystallized from diethyl ether and heptane to afford 0.5 g of brownish crystals (MS (m/e): 317.1 (MH+, 100%)). and after evaporation of the filtrate 0.6 g of slightly impure product which was used without further purification in the consecutive step. The suspension was filtered the filtrated evaporated to dryness The residue was purified with column chromatography on silica eluting with a gradient from DCM/2N NH3 in MeOH 99/1 to 19/1 The product containing fractions evaporated to dryness to yield a brown oil which was crystallized from diethyl ether and heptane

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

Procedure: Ethyl 6-hydroxy-1H-indole-2-carboxylate (4.6 g, 0.02 M) was heated under reflux with allylbromide (3 g, 2.2 ml, 0.025 M), K2CO3 (4.14 g 0.03 M) and acetone (150 ml) for 20 hours. On cooling the mixture was poured into brine and extracted into ethyl acetate, washed with brine, dried over magnesium sulphate and evaporated to dryness. The resulting crude brown solid was purified by extraction into hot 60°-80° petroleum ether to yield a yellow solid which was dried in vacuo, 4 g, 72%, mp 89°-91°. On cooling the mixture extracted into ethyl acetate washed with brine dried over magnesium sulphate evaporated to dryness The resulting crude brown solid was purified by extraction into hot 60°-80° petroleum ether to yield a yellow solid which was dried in vacuo, 4 g, 72%, mp 89°-91°

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

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

Procedure: A mixture of 1 g (4.8 mmol) ethyl-6-hydroxyindole-2-carboxylate (Journal of the American Chemical Society (1967), 89(13), 3349-50), 0.81 g (6.3 mmol) 1-isopropyl-3-pyrrolidinol, 2.83 ml (11 mmol) tri-n-butyl-phosphine and 2.56 g (9.75 mmol) 1,1′azodicarbonyl-dipiperidine in 50 ml THF was stirred at room temperature for 16 h. The suspension was filtered and the filtrated evaporated to dryness. The residue was purified with column chromatography on silica eluting with a gradient from DCM/2N NH3 in MeOH 99/1 to 19/1. The product containing fractions were combined and evaporated to dryness to yield a brown oil which was crystallized from diethyl ether and heptane to afford 0.5 g of brownish crystals (MS (m/e): 317.1 (MH+, 100%)). and after evaporation of the filtrate 0.6 g of slightly impure product which was used without further purification in the consecutive step. The suspension was filtered the filtrated evaporated to dryness The residue was purified with column chromatography on silica eluting with a gradient from DCM/2N NH3 in MeOH 99/1 to 19/1 The product containing fractions evaporated to dryness to yield a brown oil which was crystallized from diethyl ether and heptane

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

Procedure: Ethyl 6-hydroxy-1H-indole-2-carboxylate (4.6 g, 0.02 M) was heated under reflux with allylbromide (3 g, 2.2 ml, 0.025 M), K2CO3 (4.14 g 0.03 M) and acetone (150 ml) for 20 hours. On cooling the mixture was poured into brine and extracted into ethyl acetate, washed with brine, dried over magnesium sulphate and evaporated to dryness. The resulting crude brown solid was purified by extraction into hot 60°-80° petroleum ether to yield a yellow solid which was dried in vacuo, 4 g, 72%, mp 89°-91°. On cooling the mixture extracted into ethyl acetate washed with brine dried over magnesium sulphate evaporated to dryness The resulting crude brown solid was purified by extraction into hot 60°-80° petroleum ether to yield a yellow solid which was dried in vacuo, 4 g, 72%, mp 89°-91°

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