(E)-pent-3-en-2-one

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5-amino-2-bromo-4-chlorobenzonitrile (0.5 g, 2.16 mmol), (E)-pent-3-en-2-one (0.273 g, 3.24 mmol), Pd2(dba)3 (0.020 g, 0.022 mmol), di-tert-butyl(2′-methyl-[1,1′-biphenyl]-2-yl)phosphine (0.020 g, 0.065 mmol), and N-cyclohexyl-N-methylcyclohexanamine (0.633 g, 3.24 mmol) were combined in a 20 dram vial and CH3CN (4 mL) was added. The vial was evacuated and backfilled with N2, and the reaction was heated at 90° C. for 3 h. The reaction was cooled to room temperature and diluted with water, extracting 3× with EtOAc. The organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The material was purified by flash column chromatography (0-100% EtOAc/Hex). (E)-5-amino-4-chloro-2-(4-oxopent-2-en-2-yl)benzonitrile (120 mg) was obtained as a yellow solid. The vial was evacuated The reaction was cooled to room temperature diluted with water extracting 3× with EtOAc The organic layers were dried over Na2SO4 filtered concentrated in vacuo The material was purified by flash column chromatography (0-100% EtOAc/Hex)

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5-amino-2-bromo-4-chlorobenzonitrile (0.5 g, 2.16 mmol), (E)-pent-3-en-2-one (0.273 g, 3.24 mmol), Pd2(dba)3 (0.020 g, 0.022 mmol), di-tert-butyl(2′-methyl-[1,1′-biphenyl]-2-yl)phosphine (0.020 g, 0.065 mmol), and N-cyclohexyl-N-methylcyclohexanamine (0.633 g, 3.24 mmol) were combined in a 20 dram vial and CH3CN (4 mL) was added. The vial was evacuated and backfilled with N2, and the reaction was heated at 90° C. for 3 h. The reaction was cooled to room temperature and diluted with water, extracting 3× with EtOAc. The organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The material was purified by flash column chromatography (0-100% EtOAc/Hex). (E)-5-amino-4-chloro-2-(4-oxopent-2-en-2-yl)benzonitrile (120 mg) was obtained as a yellow solid. The vial was evacuated The reaction was cooled to room temperature diluted with water extracting 3× with EtOAc The organic layers were dried over Na2SO4 filtered concentrated in vacuo The material was purified by flash column chromatography (0-100% EtOAc/Hex)