Pyridine → HCID 68826481, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl 5-bromo-4-(ethoxycarbonyl)picolinate (483 mg, 1.4 mmol), trimethylsilylacetylene (206 mg, 2.1 mmol), Pd(PPh3)2Cl2 (99 mg, 0.14 mmol) and CuI (45 mg, 0.21 mmol) in triethylamine (3 mL) and THF (2 mL) in a sealed tube was passed through a stream of Ar for 5 min, and then heated at 105° C. for 1 h. The mixture was diluted with THF/CH2Cl2 (1:1), filtered through a pad of Celite®. The filtrate was concentrated in vacuo to give a residue, which was dissolved in CH2Cl2 (5 mL) and pyridine (0.5 mL) at 0° C. To this solution was added ethyl chloroformate (0.25 mL) and the resulting mixture was stirred at 0° C. for 30 min. The mixture was diluted with CH2Cl2, washed with sat. aq. K2HPO4 solution and dried over MgSO4. The product was purified by flash column chromatography (SiO2, 10% EtOAc/CH2Cl2) to afford a yellow solid (380 mg, 75%). LC-MS: m/z 363 (M+H)+.

Provenance & Evidence