Dimethylacetamide → HCID 58847064, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromo-2-(2,6-dimethylmorpholin-4-yl)benzaldehyde (0.298 g, 1.00 mmol), 1,1′-bis(dimethylphosphino)ferrocene [dppf] (0.022 g, 0.040 mmol), tris(dibenzylideneacetone)dipalladium [Pd2(dba)3] (0.018 g, 0.020 mmol), zinc dust (0.008 g, 0.12 mmol) and zinc cyanide (0.070 g, 0.60 mmol) in dimethylacetamide (2 mL) is heated 120° C. for 4 h. The reaction mixture is cooled and partitioned between dilute ammonium hydroxide and ethyl acetate. The phases are separated. The organic layer is extracted with an additional portion of ethyl acetate. The combined organic layers are dried (NaSO4) and then concentrated. The resulting residue is purified by silica gel chromatography using ethyl acetate-methylene chloride-heptane (0.5:4.0:5.5) as the eluent to afford, 172 mg (70%) of the cyano aldehyde. 1H NMR (400 MHz, CDCl3) δ 10.05, 7.97, 7.64, 7.01, 3.92-3.79, 3.14, 2.70, 1.17.

Provenance & Evidence