Sodium Carbonate → HCID 21897346, compound

Participants

Reaction Steps

A mixture of 2-amino-5-bromopyrazine (300 mg, 1.724 mmol), dichlorobis(triphenylphosphine)palladium(II) (175 mg, 0.249 mmol), 5-cyanothiophene-2-boronic acid acid (540 mg, 3.53 mmol) and a saturated aqueous sodium carbonate solution (2 mL) in ethylene glycol dimethyl ether (5 mL) and ethanol (5 mL) was heated under reflux overnight. The reaction mixture was cooled, diluted with ethyl acetate, and washed with water and a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 2/3 to 1/9 hexanes/ethyl acetate) afforded 5-(5-amino-pyrazin-2-yl)-thiophene-2-carbonitrile (49.1 mg, 14.1%) as a yellow solid: LRMS for C9H6N4S (M+H)+ at m/z=203.

Provenance & Evidence