ethyl 7-bromo-1-benzofuran-2-carboxylate

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

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

Procedure: The compound was prepared according to the procedure disclosed in Example 1a starting from benzylpiperazine (16.1 mL, 92.6 mmol) and 7-bromo-benzofuran-2-carboxylic acid ethyl ester (16.6 g, 61.7 mmol). The product was purified by flash chromatography (SiO2; hexane/EtOAc, gradient 0-50%). Yield: 14 g (63%). The compound was prepared The product was purified by flash chromatography (SiO2; hexane/EtOAc, gradient 0-50%)

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cesium carbonate (0.724 g, 2.22 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (0.081 g, 0.17 mmol) and tris(dibenzylideneacetone)dipalladium(0) (0.078 g, 0.09 mmol) were added under argon to a mixture of ethyl 7-bromobenzofuran-2-carboxylate (0.460 g, 1.71 mmol) and 1-(5-(2-(piperazin-1-yl)ethyl)indolin-1-yl)ethanone (0.491 g, 1.79 mmol) (example 38c) in dry degassed dioxane (8 mL) and the reaction was heated at 95° C. over night. After cooling to room temperature, water and DCM were added and the layers separated. The aq phase was extracted with DCM (3×). The combined organic phases were washed with water, dried (MgSO4), filtered and evaporated. The crude product was purified by flash chromatography (DCM/MeOH 95/5) to give 0.485 g (61%) of the product. in dry degassed dioxane (8 mL) After cooling to room temperature water and DCM were added the layers separated The aq phase was extracted with DCM (3×) The combined organic phases were washed with water dried (MgSO4) filtered evaporated The crude product was purified by flash chromatography (DCM/MeOH 95/5)

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ethyl 7-bromobenzofuran-2-carboxylate (0.900 g, 3.34 mmol) and 1-(2-(pyridin-2-yl)ethyl)piperazine (0.672 g, 3.51 mmol) were mixed in dry degassed dioxane (13 mL). To this mixture cesium carbonate (1.417 g, 4.35 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (0.159 g, 0.33 mmol) and tris(dibenzylideneacetone)dipalladium(0) (0.153 g, 0.17 mmol) were added under argon and the reaction was heated at 95° C. over night. Water and DCM were added and the layers were separated. The aq phase was extracted with DCM (3×). The combined organic phases were washed with water, dried (MgSO4), filtered and evaporated. The crude product was purified by flash chromatography. (SiO2; DCM/MeOH 95/5) to give 0.507 g (40%) of the title compound. in dry degassed dioxane (13 mL) the layers were separated The aq phase was extracted with DCM (3×) The combined organic phases were washed with water dried (MgSO4) filtered evaporated The crude product was purified by flash chromatography

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

Procedure: The compound was prepared according to the procedure disclosed in Example 1a starting from benzylpiperazine (16.1 mL, 92.6 mmol) and 7-bromo-benzofuran-2-carboxylic acid ethyl ester (16.6 g, 61.7 mmol). The product was purified by flash chromatography (SiO2; hexane/EtOAc, gradient 0-50%). Yield: 14 g (63%). The compound was prepared The product was purified by flash chromatography (SiO2; hexane/EtOAc, gradient 0-50%)

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

Procedure: The compound was prepared according to the procedure disclosed in Example 1a starting from benzylpiperazine (16.1 mL, 92.6 mmol) and 7-bromo-benzofuran-2-carboxylic acid ethyl ester (16.6 g, 61.7 mmol). The product was purified by flash chromatography (SiO2; hexane/EtOAc, gradient 0-50%). Yield: 14 g (63%). The compound was prepared The product was purified by flash chromatography (SiO2; hexane/EtOAc, gradient 0-50%)

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cesium carbonate (0.724 g, 2.22 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (0.081 g, 0.17 mmol) and tris(dibenzylideneacetone)dipalladium(0) (0.078 g, 0.09 mmol) were added under argon to a mixture of ethyl 7-bromobenzofuran-2-carboxylate (0.460 g, 1.71 mmol) and 1-(5-(2-(piperazin-1-yl)ethyl)indolin-1-yl)ethanone (0.491 g, 1.79 mmol) (example 38c) in dry degassed dioxane (8 mL) and the reaction was heated at 95° C. over night. After cooling to room temperature, water and DCM were added and the layers separated. The aq phase was extracted with DCM (3×). The combined organic phases were washed with water, dried (MgSO4), filtered and evaporated. The crude product was purified by flash chromatography (DCM/MeOH 95/5) to give 0.485 g (61%) of the product. in dry degassed dioxane (8 mL) After cooling to room temperature water and DCM were added the layers separated The aq phase was extracted with DCM (3×) The combined organic phases were washed with water dried (MgSO4) filtered evaporated The crude product was purified by flash chromatography (DCM/MeOH 95/5)

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cesium carbonate (0.724 g, 2.22 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (0.081 g, 0.17 mmol) and tris(dibenzylideneacetone)dipalladium(0) (0.078 g, 0.09 mmol) were added under argon to a mixture of ethyl 7-bromobenzofuran-2-carboxylate (0.460 g, 1.71 mmol) and 1-(5-(2-(piperazin-1-yl)ethyl)indolin-1-yl)ethanone (0.491 g, 1.79 mmol) (example 38c) in dry degassed dioxane (8 mL) and the reaction was heated at 95° C. over night. After cooling to room temperature, water and DCM were added and the layers separated. The aq phase was extracted with DCM (3×). The combined organic phases were washed with water, dried (MgSO4), filtered and evaporated. The crude product was purified by flash chromatography (DCM/MeOH 95/5) to give 0.485 g (61%) of the product. in dry degassed dioxane (8 mL) After cooling to room temperature water and DCM were added the layers separated The aq phase was extracted with DCM (3×) The combined organic phases were washed with water dried (MgSO4) filtered evaporated The crude product was purified by flash chromatography (DCM/MeOH 95/5)

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ethyl 7-bromobenzofuran-2-carboxylate (0.900 g, 3.34 mmol) and 1-(2-(pyridin-2-yl)ethyl)piperazine (0.672 g, 3.51 mmol) were mixed in dry degassed dioxane (13 mL). To this mixture cesium carbonate (1.417 g, 4.35 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (0.159 g, 0.33 mmol) and tris(dibenzylideneacetone)dipalladium(0) (0.153 g, 0.17 mmol) were added under argon and the reaction was heated at 95° C. over night. Water and DCM were added and the layers were separated. The aq phase was extracted with DCM (3×). The combined organic phases were washed with water, dried (MgSO4), filtered and evaporated. The crude product was purified by flash chromatography. (SiO2; DCM/MeOH 95/5) to give 0.507 g (40%) of the title compound. in dry degassed dioxane (13 mL) the layers were separated The aq phase was extracted with DCM (3×) The combined organic phases were washed with water dried (MgSO4) filtered evaporated The crude product was purified by flash chromatography

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

Procedure: The compound was prepared according to the procedure disclosed in Example 1a starting from benzylpiperazine (16.1 mL, 92.6 mmol) and 7-bromo-benzofuran-2-carboxylic acid ethyl ester (16.6 g, 61.7 mmol). The product was purified by flash chromatography (SiO2; hexane/EtOAc, gradient 0-50%). Yield: 14 g (63%). The compound was prepared The product was purified by flash chromatography (SiO2; hexane/EtOAc, gradient 0-50%)

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

Procedure: The compound was prepared according to the procedure disclosed in Example 1a starting from benzylpiperazine (16.1 mL, 92.6 mmol) and 7-bromo-benzofuran-2-carboxylic acid ethyl ester (16.6 g, 61.7 mmol). The product was purified by flash chromatography (SiO2; hexane/EtOAc, gradient 0-50%). Yield: 14 g (63%). The compound was prepared The product was purified by flash chromatography (SiO2; hexane/EtOAc, gradient 0-50%)

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cesium carbonate (0.724 g, 2.22 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (0.081 g, 0.17 mmol) and tris(dibenzylideneacetone)dipalladium(0) (0.078 g, 0.09 mmol) were added under argon to a mixture of ethyl 7-bromobenzofuran-2-carboxylate (0.460 g, 1.71 mmol) and 1-(5-(2-(piperazin-1-yl)ethyl)indolin-1-yl)ethanone (0.491 g, 1.79 mmol) (example 38c) in dry degassed dioxane (8 mL) and the reaction was heated at 95° C. over night. After cooling to room temperature, water and DCM were added and the layers separated. The aq phase was extracted with DCM (3×). The combined organic phases were washed with water, dried (MgSO4), filtered and evaporated. The crude product was purified by flash chromatography (DCM/MeOH 95/5) to give 0.485 g (61%) of the product. in dry degassed dioxane (8 mL) After cooling to room temperature water and DCM were added the layers separated The aq phase was extracted with DCM (3×) The combined organic phases were washed with water dried (MgSO4) filtered evaporated The crude product was purified by flash chromatography (DCM/MeOH 95/5)