Triethylamine → 2-Chloro-4-(2-(trimethylsilyl)ethynyl)pyridine

Participants

Reaction Steps

2-Chloro-4-iodo-pyridine (10 g, 42 mmol), palladium bis(triphenylphosphine)dichloride (2.93 g, 4.18 mmol) and triphenylphosphine (1.09 g, 4.17 mmol) are dissolved in de-gased dry THF (10 mL) and triethylamine (42 mL, 301 mmol). The resulting mixture is stirred for 1 hr at room temperature. Then Copper (I) iodide (2.3 g, 12 mmol) and ethynyl-trimethyl-silane (7.1 mL, 50 mmol) are added. The reaction mixture is stirred for 12 hrs at room temperature. The solvents are removed and the residue is diluted with water (100 mL). The mixture is extracted with EtOAc (3×250 mL) and the organic layers are combined, washed with brine, dried over anhydrous Na2SO4 and concentrated to give the crude product. Purification by silica flash column chromatography using 0.5% EtOAc in hexanes affords 4.6 g of the desired product.

Provenance & Evidence