Triethylamine → HCID 58084367, compound

Participants

Reaction Conditions

Reaction Steps

Phenylacetylene (969.2 mg, 1.044 mL, 9.490 mmol) was added dropwise to a solution of 3,5-dibromopyrazin-2-amine (2 g, 7.908 mmol), triethylamine (8.002 g, 11.02 mL, 79.08 mmol), copper (I) iodide (180.7 mg, 0.9490 mmol) and Pd(PPh3)4 (456.9 mg, 0.3954 mmol) in DMF (24 mL) and the resulting solution heated at 120° C. for 10 minutes. The reaction mixture was cooled to ambient temperature and diluted with EtOAc (20 mL) and 1 MHCl/brine (10 mL/10 mL) and the layers separated. The aqueous layer was extracted with ethyl acetate (2×20 mL) and combined organics washed with brine (2×20 mL), dried over (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography (ISCO Companion™, 80 g column, eluting with 0 to 50% EtOAc/Petroleum Ether, loaded in DCM) to give the sub-tile compound as an off-white solid (1.53 g, 70%). 1H NMR (400.0 MHz, DMSO) δ 7.04 (br s, 2H), 7.46-7.50 (m, 3H), 7.75-7.77 (m, 2H) and 8.13 (s, 1H) ppm; (ES+) 275.8.

Provenance & Evidence