Trimethylsilylacetylene → HCID 131733474, compound

Participants

Reaction Conditions

Reaction Steps

A solution of tert-butyl (5-((2-chloropyridin-4-yl)oxy)pyridin-2-yl)carbamate (0.70 g, 2.18 mmol) in DMF (5 mL) was sparged with Ar, treated with ethynyltrimethylsilane (0.64 g, 6.55 mmol), TEA (1 mL), copper(I)iodide (0.042 g, 0.22 mmol) and trans dichlorobis(triphenylphosphine)palladium(0) (0.15 g, 0.22 mmol) and heated at 75° C., under Ar, overnight. The mixture was cooled to RT, diluted with EtOAc, the solids removed via filtration through diatomaceous earth and washed with EtOAc and water. The layers of the filtrate were separated, the aqueous layer extracted with EtOAc (2×) and the combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness. The material was dissolved in MeOH (20 mL), treated with K2CO3 (0.7 g), stirred at RT for 2 h, then concentrated to dryness. The residue was treated with EtOAc, sonicated, the solids removed via filtration through diatomaceous earth, washed with EtOAc and the filtrate concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford tert-butyl (5-((2-ethynylpyridin-4-yl)oxy)pyridin-2-yl)carbamate (0.29 g, 43%). 1H NMR (400 MHz, DMSO-d6): δ 9.96 (s, 1 H), 8.41 (d, J=5.6 Hz, 1 H), 8.18 (d, J=2.8 Hz, 1 H), 7.88 (d, J=9.2 Hz, 1 H), 7.66 (m, 1 H), 7.07 (d, J=2.4 Hz, 1 H), 6.95 (m, 1 H), 4.34 (s, 1 H), 1.46 (s, 9 H); MS (ESI) m/z: 312.1 (M+H+).

Provenance & Evidence