4-Ethynylpyridine → HCID 86599495, compound

Participants

Reaction Steps

A mixture of ethyl 8-iodo-6-(trifluoromethoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylate prepared as in Example 21a, Step 2 (1.00 g, 2.07 mmole), 4-pyridylacetylene (419 uL, 4.15 mmole), CuI (39 mg, 0.207 mmole), PdCI2(dppf)2-CH2Cl2 (169 mg, 0.207 mmole) and TEA (0.866 mL, 6.21 mmole) in anhydrous toluene (10 mL) was stirred at room temperature for 5 days under a N2 atmosphere. The mixture was then diluted with hexanes and purified by silica chromatography (0% to 75% EtOAc:hexanes gradient) to give 0.34 g (36% yield) of the product as a pale yellow crystalline solid: ESHRMS m/z 458.0822 (M+H, C21H14F6NO4, Calc'd 458.0822).

Provenance & Evidence