1-methyl-1,3-dihydro-2-benzofuran

Conditions: temp:135.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The mixture of sodium 1-(2-bromo-phenyl)-ethoxymethyl trifluoroborate (30 mg, 0.092 mmol) synthesized in Example 20, tetrakis(triphenylphosphine)palladium(0) (13 mg, 0.018 mmol), cesium carbonate (90 mg, 0.28 mmol), 1,4-dioxane (1.0 ml), and water (0.10 ml) was stirred at 135° C. for 90 minutes under microwave irradiation. The reaction mixture was cooled to room temperature, and then water and heptane were added thereto, followed by filtration with Celite. The organic layer of the filtrate was separated and washed with saturated saline. The solvents were evaporated under reduced pressure from the organic layer, and then the obtained residue was purified with silica gel column chromatography (hexane alone→hexane:diethyl ether=30:1), thereby obtaining the entitled compound (35.7 mg, 41%). The reaction mixture was cooled to room temperature followed by filtration with Celite The organic layer of the filtrate was separated washed with saturated saline The solvents were evaporated under reduced pressure from the organic layer the obtained residue was purified with silica gel column chromatography (hexane alone→hexane

Conditions: temp:135.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The mixture of sodium 1-(2-bromo-phenyl)-ethoxymethyl trifluoroborate (30 mg, 0.092 mmol) synthesized in Example 20, tetrakis(triphenylphosphine)palladium(0) (13 mg, 0.018 mmol), cesium carbonate (90 mg, 0.28 mmol), 1,4-dioxane (1.0 ml), and water (0.10 ml) was stirred at 135° C. for 90 minutes under microwave irradiation. The reaction mixture was cooled to room temperature, and then water and heptane were added thereto, followed by filtration with Celite. The organic layer of the filtrate was separated and washed with saturated saline. The solvents were evaporated under reduced pressure from the organic layer, and then the obtained residue was purified with silica gel column chromatography (hexane alone→hexane:diethyl ether=30:1), thereby obtaining the entitled compound (35.7 mg, 41%). The reaction mixture was cooled to room temperature followed by filtration with Celite The organic layer of the filtrate was separated washed with saturated saline The solvents were evaporated under reduced pressure from the organic layer the obtained residue was purified with silica gel column chromatography (hexane alone→hexane

Conditions: temp:135.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The mixture of sodium 1-(2-bromo-phenyl)-ethoxymethyl trifluoroborate (30 mg, 0.092 mmol) synthesized in Example 20, tetrakis(triphenylphosphine)palladium(0) (13 mg, 0.018 mmol), cesium carbonate (90 mg, 0.28 mmol), 1,4-dioxane (1.0 ml), and water (0.10 ml) was stirred at 135° C. for 90 minutes under microwave irradiation. The reaction mixture was cooled to room temperature, and then water and heptane were added thereto, followed by filtration with Celite. The organic layer of the filtrate was separated and washed with saturated saline. The solvents were evaporated under reduced pressure from the organic layer, and then the obtained residue was purified with silica gel column chromatography (hexane alone→hexane:diethyl ether=30:1), thereby obtaining the entitled compound (35.7 mg, 41%). The reaction mixture was cooled to room temperature followed by filtration with Celite The organic layer of the filtrate was separated washed with saturated saline The solvents were evaporated under reduced pressure from the organic layer the obtained residue was purified with silica gel column chromatography (hexane alone→hexane