1-[(4-iodophenyl)methyl]pyrrolidine

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: A reaction mixture of 1 g (3.48 mmol) of 1-(4-iodobenzyl)pyrrolidine, 5 mL of piperidine, 105 mg (0.091 mmol) of tetrakistriphenylphosphine palladium, and 10 mg (0.053 mmol) of copper (I) iodide is cooled to 0° C. At this temperature, 0.59 mL (4.18 mmol) of trimethylsilylacetylene is added dropwise and then the cooling bath is removed. It is stirred for 3 hours at ambient temperature, then combined with a saturated aqueous ammonium chloride solution, and extracted with dichloromethane. The organic phase is dried over sodium sulfate. The purification is carried out by column chromatography on silica gel (eluant: cyclohexane/ethyl acetate (1:1)). Yield: 0.75 g (83.6% of theory); C16H23NSi (M=257.45); calc.: molecular ion peak (M+H)+: 258; found: molecular ion peak (M+H)+: 258. the cooling bath is removed extracted with dichloromethane The organic phase is dried over sodium sulfate The purification

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

実験手順: 10 mL of acetonitrile is degassed and combined with 0.35 mL (2 mmol) of ethyldiisopropylamine and 0.2 g (0.69 mmol) of 1-(4-iodobenzyl)pyrrolidine. Then the mixture is again degassed and 13 mg of copper (I) iodide, 34 mg of tetrakistriphenylphosphine palladium, and 137 mg (0.75 mmol) of propynoic acid-(4-prop-1-ynylphenyl)amide are then added in succession. The reaction mixture is stirred for 24 hours at ambient temperature and then combined with 60 mg of propynoic acid-(4-prop-1-ynylphenyl)amide. After 24 hours, the mixture is evaporated down. The purification is carried out by column chromatography on silica gel (dichloromethane/methanol/ammonia (30:1:0.1 to 20:1:0.1)). Yield: 24 mg (10% of theory); C23H22N2O (M=342.44); calc.: molecular ion peak (M+H)+: 343; found: molecular ion peak (M+H)+: 343; Rf value: 0.2 (silica gel, dichloromethane/methanol/ammonia=10:1:0.1). 10 mL of acetonitrile is degassed Then the mixture is again degassed After 24 hours the mixture is evaporated down The purification

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

実験手順: 10 mL of acetonitrile is degassed and combined with 0.35 mL (2 mmol) of ethyldiisopropylamine and 0.2 g (0.69 mmol) of 1-(4-iodobenzyl)pyrrolidine. Then the mixture is again degassed and 13 mg of copper (I) iodide, 34 mg of tetrakistriphenylphosphine palladium, and 137 mg (0.75 mmol) of propynoic acid-(4-prop-1-ynylphenyl)amide are then added in succession. The reaction mixture is stirred for 24 hours at ambient temperature and then combined with 60 mg of propynoic acid-(4-prop-1-ynylphenyl)amide. After 24 hours, the mixture is evaporated down. The purification is carried out by column chromatography on silica gel (dichloromethane/methanol/ammonia (30:1:0.1 to 20:1:0.1)). Yield: 24 mg (10% of theory); C23H22N2O (M=342.44); calc.: molecular ion peak (M+H)+: 343; found: molecular ion peak (M+H)+: 343; Rf value: 0.2 (silica gel, dichloromethane/methanol/ammonia=10:1:0.1). 10 mL of acetonitrile is degassed Then the mixture is again degassed After 24 hours the mixture is evaporated down The purification

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: Under an N2 atmosphere 221 mg (0.68 mmol) Cs2CO3, 4 mg (0.02 mmol) CuI and 23 mg (0.02 mmol) tetrakis-triphenylphosphane-palladium are added to a solution of 110 mg (0.45 mmol) 5-(4-chloro-phenyl)-2-prop-2-ynyloxy-pyridine and 129 mg (0.45 mmol) 1-(4-iodo-benzyl)-pyrrolidine in 9 mL THF and the reaction mixture is stirred for 4.5 h at RT. The mixture is evaporated down i. vac., the residue is combined with 20 mL 3% NH3 solution and 40 mL EtOAc, the organic phase is separated off and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified first by HPLC and then by chromatography (silica gel, DCM/MeOH/NH3 19:1:0.1). The mixture is evaporated down i the organic phase is separated off dried over Na2SO4 is purified first by HPLC

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

実験手順: A reaction mixture of 1 g (3.48 mmol) of 1-(4-iodobenzyl)pyrrolidine, 5 mL of piperidine, 105 mg (0.091 mmol) of tetrakistriphenylphosphine palladium, and 10 mg (0.053 mmol) of copper (I) iodide is cooled to 0° C. At this temperature, 0.59 mL (4.18 mmol) of trimethylsilylacetylene is added dropwise and then the cooling bath is removed. It is stirred for 3 hours at ambient temperature, then combined with a saturated aqueous ammonium chloride solution, and extracted with dichloromethane. The organic phase is dried over sodium sulfate. The purification is carried out by column chromatography on silica gel (eluant: cyclohexane/ethyl acetate (1:1)). Yield: 0.75 g (83.6% of theory); C16H23NSi (M=257.45); calc.: molecular ion peak (M+H)+: 258; found: molecular ion peak (M+H)+: 258. the cooling bath is removed extracted with dichloromethane The organic phase is dried over sodium sulfate The purification

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

実験手順: 10 mL of acetonitrile is degassed and combined with 0.35 mL (2 mmol) of ethyldiisopropylamine and 0.2 g (0.69 mmol) of 1-(4-iodobenzyl)pyrrolidine. Then the mixture is again degassed and 13 mg of copper (I) iodide, 34 mg of tetrakistriphenylphosphine palladium, and 137 mg (0.75 mmol) of propynoic acid-(4-prop-1-ynylphenyl)amide are then added in succession. The reaction mixture is stirred for 24 hours at ambient temperature and then combined with 60 mg of propynoic acid-(4-prop-1-ynylphenyl)amide. After 24 hours, the mixture is evaporated down. The purification is carried out by column chromatography on silica gel (dichloromethane/methanol/ammonia (30:1:0.1 to 20:1:0.1)). Yield: 24 mg (10% of theory); C23H22N2O (M=342.44); calc.: molecular ion peak (M+H)+: 343; found: molecular ion peak (M+H)+: 343; Rf value: 0.2 (silica gel, dichloromethane/methanol/ammonia=10:1:0.1). 10 mL of acetonitrile is degassed Then the mixture is again degassed After 24 hours the mixture is evaporated down The purification