Dimethylformamide → HCID 68672414, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1.17 g (5.10 mmol) of (2-chloro-6-(dimethylamino)pyridin-4-yl)methyl acetate in 10 mL of DMF (degassed) was added 488 mg (4.16 mmol) of Zn(CN)2 and 519 mg (0.449 mmol) of Pd(PPh3)4. The mixture was stirred at 80° C. and more Pd(PPh3)4 was added in the following quantities at various intervals in a period of 10 h: 486 mg (50 min.), 708 mg (3 h), 657 mg (6 h). The temperature was increased to 100° C. and stirring was continued for about 11 h. Ethyl acetate and 50 mL of 10% NH4OH solution were added. The aqueous layer was extracted with EtOAc, and the combined extracts were washed with brine. The aqueous layer (brine) was extracted with EtOAc, and the combined extracts were dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (30% EtOAc/hexanes) provided 284 mg of (2-cyano-6-(dimethylamino)pyridin-4-yl)methyl acetate as a pale yellow solid.

Provenance & Evidence