3-Buten-2-ol → HCID 89922494, compound

Participants

Reaction Conditions

Reaction Steps

5-amino-2-bromo-4-chlorobenzonitrile (1.1 g, 4.75 mmol), but-3-en-2-ol (0.445 g, 6.18 mmol), Pd2(dba)3 (0.044 g, 0.048 mmol), di-tert-butyl(2′-methyl-[1,1′-biphenyl]-2-yl)phosphine (0.045 g, 0.143 mmol), and N-cyclohexyl-N-methylcyclohexanamine (1.392 g, 7.13 mmol) were combined in a 20 dram vial and CH3CN (8 mL) was added. The vial was evacuated and backfilled with Ar 4×, and the reaction was heated at 90° C. for 45 min. 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 then purified by flash column chromatography (0-70% EtOAc/Hex; 80 g column). 5-amino-4-chloro-2-(3-oxobutyl)benzonitrile (635 mg) was obtained as yellow foam.

Provenance & Evidence