Triethylamine → HCID 58495570, compound

Participants

Reaction Steps

Add cyclohexylacetylene (1.1 mL, 8.4 mmol) to a slurry of N-(tert-butoxycarbonyl)-4-bromo-benzylamine (2 g, 6.9 mmol), dichlorobis(triphenylphosphine)palladium (147 mg, 0.2 mmol), copper(I) iodide (67 mg, 0.4 mmol) and triethylamine (1.4 mL, 9.7 mmol) in DMF (7 mL). Stir the reaction in a sealed flask at 110° C. for 16 h. Cool to room temperature, dilute with water (10 mL) and hexane/EtOAc (1:1, 100 mL). Filter the bi-phasic mixture through Celite®, collect the organic phase and wash with 5% aqueous NaCl (3×30 mL). Concentrate the organic phase in vacuo and purify by chromatography on silica gel (120 g) eluting with hexane/EtOAc (20:1 to 3:2 gradient) to obtain the desired intermediate (0.75 g, 34%). MS (ES+) m/z: 258 [M-(t-Bu)+H]+.

Provenance & Evidence