Imidazole → HCID 59472788, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-chloronicotinaldehyde (5.0 g, 35 mmol) in 60 mL of DMF was treated with 4-methylimidazole (5.8 g, 71 mmol) and K2CO3 (7.3 g, 53 mmol) and warmed to 100° C. Stirred overnight. Diluted with EtOAc, washed with sat'd NaHCO3, dried (Na2SO4), concentrated to give a 4:1 mixture of imidazole regioisomers. Recrystallization from EtOH gave a single regioisomer. A portion of the aldehyde (500 mg, 2.67 mmol) was dissolved in 10 mL of MeOH, treated with K2CO3 (740 mg, 5.4 mmol) and dimethyl (1-diazo-2-oxopropyl)phosphonate (620 mg, 3.2 mmol) and stirred overnight. Diluted with DCM and washed with water. Dried (Na2SO4), conc. Chromatography on silica (0-20% MeOH/DCM) gave the desired alkyne (276 mg; 56%):

Provenance & Evidence