Triethylamine → 2-Amino-5-thiophen-3-ylpyridine-3-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

150 mg (0.605 mmol) of 2-amino-5-iodopyridine-3-carbaldehyde and 115 mg (0.605 mmol) of potassium 3-thiophenetrifluoroborate are suspended in 4 ml of ethanol in a nitrogen-filled reaction vessel, and 251 μl (1.814 mmol) of triethylamine and 22.1 mg (0.030 mmol) of [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride are added. The reaction mixture is stirred at 80° C. for 14 h under a nitrogen protective atmosphere. The reaction mixture is cooled to room temperature and diluted with water/ethyl acetate and filtered off. The organic phase is separated, and the aqueous phase is extracted a further 2× with ethyl acetate. The combined organic phases are dried over sodium sulfate, filtered, and the solvent is removed, giving 2-amino-5-thiophen-3-ylpyridine-3-carbaldehyde; HPLC-MS [M+H]+ 205.2.

Provenance & Evidence