Dimethylformamide → HCID 25263815, compound

Participants

Reaction Conditions

Reaction Steps

A 20 mL vial was charged with Pd(PPh3)4 (0.159 g, 0.138 mmol), zinc cyanide (0.243 g, 2.07 mmol), 3 mL of DMF, and 1-[1-(4-bromophenyl)-5-methoxy-1H-pyrazol-3-yl]-N—[(1R)-1-(3-chlorophenyl)ethyl]ethanamine 85 (0.600 g, 1.38 mmol) as a >20:1 mixture of diastereomers. The reaction mixture was heated to 100° C. After 3 d, an additional 10 mol % of Pd(PPh3)4 and 2 equivalents of ZnCN2 were added. The reaction mixture was heated in a microwave to 180° C. for 15 min. The reaction mixture was cooled to room temperature, dissolved in EtOAc, washed with water and brine, dried, and concentrated. Purification by flash column chromatography on silica gel (2% MeOH in DCM) gave 443-(1-{[(1R)-1-(3-chlorophenyl)ethyl]amino}ethyl)-5-methoxy-1H-pyrazol-1-yl]benzonitrile 96 as a >20:1 mixture of diastereomers. Mass spectrum: calculated for C2H21ClN4O 380.1; found 381.2 (M++1).

Provenance & Evidence