反应详情

温度

85 °C

A solution of (S)—N-[methyl(oxo)phenyl-λ6-sulfanylidene]-5-[(trimethylsilyl)ethynyl]-nicotinamide (150 mg, 0.42 mmol) and 2-hydroxy-5-iodopyridine (105.4 mg, 0.46 mmol) in DMF (2.1 mL) was degassed (vacuum and argon). The resulting solution was treated tetrakis(triphenylphosphine)palladium(0) (24 mg, 0.021 mmol), triethylamine (0.08 mL, 0.55 mmol), and CuI (8 mg, 0.042 mmol). The reaction mixture was then heated to 85° C. and tetrabutylammonium fluoride (1.0 M solution in THF, 0.46 mL, 0.46 mmol) was added dropwise over 10 min. The reaction was allowed to be stirred at 85° C. for 2 hours. The reaction mixture was partitioned between EtOAc and H2O. The organic extracts and associated solid were collected and concentrated. The residue was purified by chromatography (silica gel, gradient elution MeOH—CHCl3: 1:100-1:4). The product containing fractions were collected, concentrated, and the brown solid residue was triturated with a combination of MeOH and EtOAc. The resulting mixture was filtered and the filtrate allowed to stand at room temperature. The solid which precipitated from solution was collected and dried to give the title compound as a white solid (11 mg).

1. customThe reaction mixture was partitioned between EtOAc and H2O
2. customwere collected
3. concentrationconcentrated
4. customThe residue was purified by chromatography (silica gel, gradient elution MeOH—CHCl3: 1:100-1:4)
5. additionThe product containing fractions
6. customwere collected
7. concentrationconcentrated
8. customthe brown solid residue was triturated with a combination of MeOH and EtOAc
9. filtrationThe resulting mixture was filtered
10. customto stand at room temperature
11. customThe solid which precipitated from solution
12. customwas collected
13. customdried