1-(1-benzofuran-2-yl)-2-bromoethanone

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

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

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

Procedure: Benzofuran-2-yl methyl ketone (1.60 g, 10 mM) was dissolved in ether (20 mL). Under stirring of the mixture at room temperature, bromine (1.60 g) was added thereto. The resultant mixture was stirred for 10 minutes at room temperature, and poured in saturated sodium hydrogencarbonate solution, followed by extraction with ether (80 mL). The extract was washed with saturated brine and dried over magnesium sulfate, and the solvent was removed. Hexane was added to the residue and crystals were collected through filtration. The crystals were washed with hexane and dried, whereby 1.55 g of the product of interest was obtained (yield 69.4%). followed by extraction with ether (80 mL) The extract was washed with saturated brine dried over magnesium sulfate the solvent was removed Hexane was added to the residue and crystals were collected through filtration The crystals were washed with hexane dried

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

Procedure: Benzofuran-2-yl methyl ketone (1.60 g, 10 mM) was dissolved in ether (20 mL). Under stirring of the mixture at room temperature, bromine (1.60 g) was added thereto. The resultant mixture was stirred for 10 minutes at room temperature, and poured in saturated sodium hydrogencarbonate solution, followed by extraction with ether (80 mL). The extract was washed with saturated brine and dried over magnesium sulfate, and the solvent was removed. Hexane was added to the residue and crystals were collected through filtration. The crystals were washed with hexane and dried, whereby 1.55 g of the product of interest was obtained (yield 69.4%). followed by extraction with ether (80 mL) The extract was washed with saturated brine dried over magnesium sulfate the solvent was removed Hexane was added to the residue and crystals were collected through filtration The crystals were washed with hexane dried

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.022 g, 0.075 mmol) was diluted in CHCl3 (1.8 mL) and dispensed directly into a 1 dram vial containing 1-(1-benzofuran-2-yl)-2-bromoethanone (0.027 g, 0.112 mmol). Added CH3CN (1.2 mL), the vial was fitted with stirring bar and capped. The reaction was stirred and heated at 60° C. for 24 h and then concentrated under vacuum to give a white solid. This residue was dissolved in DMSO and purified by preparatory HPLC (without TFA) to give the title compound (0.022 g, 57.4%). LC/MS ESI RT 1.98 min, M+452 capped The reaction was stirred concentrated under vacuum to give a white solid purified by preparatory HPLC (without TFA)

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.022 g, 0.075 mmol) was diluted in CHCl3 (1.8 mL) and dispensed directly into a 1 dram vial containing 1-(1-benzofuran-2-yl)-2-bromoethanone (0.027 g, 0.112 mmol). Added CH3CN (1.2 mL), the vial was fitted with stirring bar and capped. The reaction was stirred and heated at 60° C. for 24 h and then concentrated under vacuum to give a white solid. This residue was dissolved in DMSO and purified by preparatory HPLC (without TFA) to give the title compound (0.022 g, 57.4%). LC/MS ESI RT 1.98 min, M+452 capped The reaction was stirred concentrated under vacuum to give a white solid purified by preparatory HPLC (without TFA)

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

Procedure: To 5,6-dichloro-2-(2,2,2-trifluoro-ethyl)-1H-benzimidazole (460.5 mg) in DMF (5 mL) was added sodium hydride (103 mg of 60% in oil dispersion). The resulting mixture was stirred at room temperature for 5 min. To the dark green solution was added 1-(1-benzofuran-2-yl)-2-bromoethan-1-one (633 mg) and the resulting mixture was stirred at room temperature overnight. The reaction mixture was quenched with water, extracted with EtOAc, and dried over Na2SO4. The crude product was purified by silica gel chromatography (10%-40% EtOAc/hexanes) to yield the title compound as a yellow solid. the resulting mixture was stirred at room temperature overnight The reaction mixture was quenched with water extracted with EtOAc dried over Na2SO4 The crude product was purified by silica gel chromatography (10%-40% EtOAc/hexanes)

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

Procedure: To 5,6-dichloro-2-(2,2,2-trifluoro-ethyl)-1H-benzimidazole (460.5 mg) in DMF (5 mL) was added sodium hydride (103 mg of 60% in oil dispersion). The resulting mixture was stirred at room temperature for 5 min. To the dark green solution was added 1-(1-benzofuran-2-yl)-2-bromoethan-1-one (633 mg) and the resulting mixture was stirred at room temperature overnight. The reaction mixture was quenched with water, extracted with EtOAc, and dried over Na2SO4. The crude product was purified by silica gel chromatography (10%-40% EtOAc/hexanes) to yield the title compound as a yellow solid. the resulting mixture was stirred at room temperature overnight The reaction mixture was quenched with water extracted with EtOAc dried over Na2SO4 The crude product was purified by silica gel chromatography (10%-40% EtOAc/hexanes)

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

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

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.022 g, 0.075 mmol) was diluted in CHCl3 (1.8 mL) and dispensed directly into a 1 dram vial containing 1-(1-benzofuran-2-yl)-2-bromoethanone (0.027 g, 0.112 mmol). Added CH3CN (1.2 mL), the vial was fitted with stirring bar and capped. The reaction was stirred and heated at 60° C. for 24 h and then concentrated under vacuum to give a white solid. This residue was dissolved in DMSO and purified by preparatory HPLC (without TFA) to give the title compound (0.022 g, 57.4%). LC/MS ESI RT 1.98 min, M+452 capped The reaction was stirred concentrated under vacuum to give a white solid purified by preparatory HPLC (without TFA)

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.022 g, 0.075 mmol) was diluted in CHCl3 (1.8 mL) and dispensed directly into a 1 dram vial containing 1-(1-benzofuran-2-yl)-2-bromoethanone (0.027 g, 0.112 mmol). Added CH3CN (1.2 mL), the vial was fitted with stirring bar and capped. The reaction was stirred and heated at 60° C. for 24 h and then concentrated under vacuum to give a white solid. This residue was dissolved in DMSO and purified by preparatory HPLC (without TFA) to give the title compound (0.022 g, 57.4%). LC/MS ESI RT 1.98 min, M+452 capped The reaction was stirred concentrated under vacuum to give a white solid purified by preparatory HPLC (without TFA)