4-(chloromethyl)-1-(2-methylpropyl)-2-(trifluoromethyl)benzene

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

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

Procedure: tert-Butyl 2-(7-hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (0.04 g, 0.139 mmol) was dissolved in DMF (1.0 mL) and cesium carbonate (0.045 g, 0.139 mmol) and 4-(chloromethyl)-1-isobutyl-2-(trifluoromethyl)benzene (0.035 g, 0.139 mmol) was added. The reaction mixture was stirred at room temperature for 48 h and then filtered through Celite®. The filtrate was partitioned between EtOAc and water. The aqueous layer was extracted two additional times with EtOAc and the combined extracts were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to provide the title compound (58 mg). LCMS m/z=502.6 [M+H]+. filtered through Celite® The filtrate was partitioned between EtOAc and water The aqueous layer was extracted two additional times with EtOAc the combined extracts were dried over sodium sulfate filtered concentrated under reduced pressure The residue was purified by silica gel column chromatography

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

Procedure: tert-Butyl 2-(7-hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (0.04 g, 0.139 mmol) was dissolved in DMF (1.0 mL) and cesium carbonate (0.045 g, 0.139 mmol) and 4-(chloromethyl)-1-isobutyl-2-(trifluoromethyl)benzene (0.035 g, 0.139 mmol) was added. The reaction mixture was stirred at room temperature for 48 h and then filtered through Celite®. The filtrate was partitioned between EtOAc and water. The aqueous layer was extracted two additional times with EtOAc and the combined extracts were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to provide the title compound (58 mg). LCMS m/z=502.6 [M+H]+. filtered through Celite® The filtrate was partitioned between EtOAc and water The aqueous layer was extracted two additional times with EtOAc the combined extracts were dried over sodium sulfate filtered concentrated under reduced pressure The residue was purified by silica gel column chromatography

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

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

Procedure: tert-Butyl 2-(7-hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (0.04 g, 0.139 mmol) was dissolved in DMF (1.0 mL) and cesium carbonate (0.045 g, 0.139 mmol) and 4-(chloromethyl)-1-isobutyl-2-(trifluoromethyl)benzene (0.035 g, 0.139 mmol) was added. The reaction mixture was stirred at room temperature for 48 h and then filtered through Celite®. The filtrate was partitioned between EtOAc and water. The aqueous layer was extracted two additional times with EtOAc and the combined extracts were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to provide the title compound (58 mg). LCMS m/z=502.6 [M+H]+. filtered through Celite® The filtrate was partitioned between EtOAc and water The aqueous layer was extracted two additional times with EtOAc the combined extracts were dried over sodium sulfate filtered concentrated under reduced pressure The residue was purified by silica gel column chromatography

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

Procedure: tert-Butyl 2-(7-hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (0.04 g, 0.139 mmol) was dissolved in DMF (1.0 mL) and cesium carbonate (0.045 g, 0.139 mmol) and 4-(chloromethyl)-1-isobutyl-2-(trifluoromethyl)benzene (0.035 g, 0.139 mmol) was added. The reaction mixture was stirred at room temperature for 48 h and then filtered through Celite®. The filtrate was partitioned between EtOAc and water. The aqueous layer was extracted two additional times with EtOAc and the combined extracts were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to provide the title compound (58 mg). LCMS m/z=502.6 [M+H]+. filtered through Celite® The filtrate was partitioned between EtOAc and water The aqueous layer was extracted two additional times with EtOAc the combined extracts were dried over sodium sulfate filtered concentrated under reduced pressure The residue was purified by silica gel column chromatography