Dimethylformamide → (R,Z)-4-(3-(hydroxyimino)-3-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-1-o-tolylpropyl)benzonitrile

Participants

Reaction Conditions

Reaction Steps

To a microwave vial was added (R)-5-(3-(4-bromophenyl)-1-(hydroxyimino)-3-o-tolylpropyl)-1-methylpyridin-2(1H)-one (example 223; 98 mg, 230 μmol), 1,1′-bis(diphenyl-phosphino)ferrocene (3.83 mg, 6.91 μmol), tris(dibenzylideneacetone)dipalladium(0) (2.11 mg, 2.3 μmol), zinc cyanide (14.9 mg, 127 μmol), zinc (0.6 mg, 9 μmol) and zinc acetate (1.69 mg, 9.22 μmol) in N,N-dimethylformamide (1.5 mL) and water (15 μl). The vial was capped and heated at 180° C. for 35 min, then at 200° C. for 10 min, then the reaction mixture was concentrated in vacuo and the residue purified by chromatography (SiO2, gradient dichloro-methane to dichloromethane/methanol/25% aq. ammonia solution 95:5:0.25) to produce (R,E)-4-(3-(hydroxyimino)-3-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-1-o-tolylpropyl)benzonitrile (8 mg, 9%; dark brown gum, MS (ESI+): m/z=: 372.2 [M+H]+) and (R,Z)-4-(3-(hydroxyimino)-3-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-1-o-tolylpropyl)benzonitrile (6 mg, 6%; dark brown gum, MS (ESI+): m/z=: 372.2 [M+H]+).

Provenance & Evidence