1-(3-bromophenyl)pyrrolidin-2-one

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

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirring solution of 1,3-dibromobenzene (3 g, 12.72 mmol) in 1,4-dioxane (100 mL) was added 2-pyrrolidinone (0.975 mL, 12.72 mmol), palladium(II) acetate (0.143 g, 0.636 mmol), xantphos (0.736 g, 1.272 mmol) and cesium carbonate (8.29 g, 25.4 mmol). The mixture was then heated at 100° C. overnight. The reaction mixture was diluted with ethyl acetate (100 mL). The organic phase was washed with water (100 mL). The organic phase was collected, and the aqueous phase further extracted with ethyl acetate (2×50 mL). The organic phases were combined, dried over MgSO4, filtered and removed solvent under vacuo. The residue was purified on silica gel, eluting with a gradient of 0-40% ethyl acetate in cyclohexane to give the title compound (2.06 g). LCMS (A): m/z (M+H)+ 240/242, C10H10BrNO requires 239/241 (acidic). The organic phase was washed with water (100 mL) The organic phase was collected the aqueous phase further extracted with ethyl acetate (2×50 mL) dried over MgSO4 filtered removed solvent under vacuo The residue was purified on silica gel eluting with a gradient of 0-40% ethyl acetate in cyclohexane

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirring solution of 1,3-dibromobenzene (3 g, 12.72 mmol) in 1,4-dioxane (100 mL) was added 2-pyrrolidinone (0.975 mL, 12.72 mmol), palladium(II) acetate (0.143 g, 0.636 mmol), xantphos (0.736 g, 1.272 mmol) and cesium carbonate (8.29 g, 25.4 mmol). The mixture was then heated at 100° C. overnight. The reaction mixture was diluted with ethyl acetate (100 mL). The organic phase was washed with water (100 mL). The organic phase was collected, and the aqueous phase further extracted with ethyl acetate (2×50 mL). The organic phases were combined, dried over MgSO4, filtered and removed solvent under vacuo. The residue was purified on silica gel, eluting with a gradient of 0-40% ethyl acetate in cyclohexane to give the title compound (2.06 g). LCMS (A): m/z (M+H)+ 240/242, C10H10BrNO requires 239/241 (acidic). The organic phase was washed with water (100 mL) The organic phase was collected the aqueous phase further extracted with ethyl acetate (2×50 mL) dried over MgSO4 filtered removed solvent under vacuo The residue was purified on silica gel eluting with a gradient of 0-40% ethyl acetate in cyclohexane

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirring solution of 1,3-dibromobenzene (3 g, 12.72 mmol) in 1,4-dioxane (100 mL) was added 2-pyrrolidinone (0.975 mL, 12.72 mmol), palladium(II) acetate (0.143 g, 0.636 mmol), xantphos (0.736 g, 1.272 mmol) and cesium carbonate (8.29 g, 25.4 mmol). The mixture was then heated at 100° C. overnight. The reaction mixture was diluted with ethyl acetate (100 mL). The organic phase was washed with water (100 mL). The organic phase was collected, and the aqueous phase further extracted with ethyl acetate (2×50 mL). The organic phases were combined, dried over MgSO4, filtered and removed solvent under vacuo. The residue was purified on silica gel, eluting with a gradient of 0-40% ethyl acetate in cyclohexane to give the title compound (2.06 g). LCMS (A): m/z (M+H)+ 240/242, C10H10BrNO requires 239/241 (acidic). The organic phase was washed with water (100 mL) The organic phase was collected the aqueous phase further extracted with ethyl acetate (2×50 mL) dried over MgSO4 filtered removed solvent under vacuo The residue was purified on silica gel eluting with a gradient of 0-40% ethyl acetate in cyclohexane

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

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

Procedure: To a flask charged with Cs2CO3 (4.74 g), Copper(I) bromide (99 mg), and ethyl-2-cyclohexanone-carboxylate (248 mg) was added 3 mL of DMSO under an argon atmosphere. 1-bromo-3-iodobenzene (2.0 g) was added followed by a solution of 2-pyrrolidinone (715 mg) in 3 mL of DMSO. The reaction mixture was stirred at rt for 16 h and then heated to 90° C. for 24 h. The mixture was filtered over celite, concentrated and purified by flash chromatography (65:35 hexanes:ethyl acetate) to afford 983 mg of 1-(3-Bromo-phenyl)-pyrrolidin-2-one as a brown solid. heated to 90° C. for 24 h The mixture was filtered over celite, concentrated purified by flash chromatography (65:35 hexanes:ethyl acetate)

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirring solution of 1,3-dibromobenzene (3 g, 12.72 mmol) in 1,4-dioxane (100 mL) was added 2-pyrrolidinone (0.975 mL, 12.72 mmol), palladium(II) acetate (0.143 g, 0.636 mmol), xantphos (0.736 g, 1.272 mmol) and cesium carbonate (8.29 g, 25.4 mmol). The mixture was then heated at 100° C. overnight. The reaction mixture was diluted with ethyl acetate (100 mL). The organic phase was washed with water (100 mL). The organic phase was collected, and the aqueous phase further extracted with ethyl acetate (2×50 mL). The organic phases were combined, dried over MgSO4, filtered and removed solvent under vacuo. The residue was purified on silica gel, eluting with a gradient of 0-40% ethyl acetate in cyclohexane to give the title compound (2.06 g). LCMS (A): m/z (M+H)+ 240/242, C10H10BrNO requires 239/241 (acidic). The organic phase was washed with water (100 mL) The organic phase was collected the aqueous phase further extracted with ethyl acetate (2×50 mL) dried over MgSO4 filtered removed solvent under vacuo The residue was purified on silica gel eluting with a gradient of 0-40% ethyl acetate in cyclohexane