Trimethylsilylacetylene → HCID 67959875, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (4R)-tert-butyl 4-(6-(5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)pyrazin-2-yloxy)-6-azaspiro[2.5]octane-6-carboxylate (579 mg, 0.991 mmol), copper(I) iodide (37.7 mg, 0.198 mmol), PdCl2(Amphos) (70.1 mg, 0.099 mmol), N-ethyl-N-isopropylpropan-2-amine (530 μL, 2.97 mmol), and ethynyltrimethylsilane (208 μL, 1.486 mmol) in DMF (9906 μL) was heated in the microwave for 15 min at 160° C. The crude product was adsorbed onto silica and was purified via automated flash chromatography (silica gel) with 100% hexanes to 20% EtOAc/hexanes to give (4R)-tert-butyl 4-(6-(1-(tetrahydro-2H-pyran-2-yl)-5-((trimethylsilyl)ethynyl)-1H-indazol-3-yl)pyrazin-2-yloxy)-6-azaspiro[2.5]octane-6-carboxylate (596 mg, 0.990 mmol, 100% yield) as a yellow foam. MS (ESI, pos. ion) m/z: 602.3 (M+1).

Provenance & Evidence