Tetrahydrofuran → HCID 66570997, compound

Participants

Reaction Conditions

Reaction Steps

5-Trimethylsilanylethynyl-pyridine-2-carboxylic acid tert-butyl-methyl-amide (Example 3, step 2) (60 mg, 0.2 mmol) was dissolved in DMF (1 ml). 1-Fluoro-3-iodobenzene (74 mg, 0.33 mmol, 1.6 equiv.), Et3N (87 μl, 0.62 mmol, 3 equiv.), Bis-(triphenylphosphine)-palladium(II)dichloride (7 mg, 10.4 μmol, 0.05 equiv.) and copper(I)iodide (0.4 mg, 2 μmol, 0.01 equiv.) were added under nitrogen and the mixture was heated to 70° C. TBAF 1M in THF (230 μl, 0.23 mmol, 1.1 equiv.) was added dropwise over a period of 20 minutes at 70° C. The reaction mixture was stirred for 30 minutes at 70° C. and evaporated in presence of Isolute® sorbent to dryness. The crude product was purified by flash chromatography with a 20 g silica gel column eluting with heptane:ethyl acetate 100:0→70:30. The desired 5-(3-fluoro-phenylethynyl)-pyridine-2-carboxylic acid tert-butyl-methyl-amide (64 mg, 99% yield) was obtained as a colorless oil, MS: m/e=311.5 (M+H+).

Provenance & Evidence