Triethylamine → HCID 86667832, compound

Participants

Reaction Conditions

Reaction Steps

3-Ethynylphenol (560.5 mg, 310.9 μL, 4.745 mmol) was added dropwise to a solution of 3,5-dibromopyrazin-2-amine (1 g, 3.954 mmol), triethylamine (4.001 g, 5.511 mL, 39.54 mmol), copper (I) iodide (90.37 mg, 0.4745 mmol) and Pd(PPh3)4 (228.5 mg, 0.1977 mmol) in DMF (10 mL) and the resulting solution heated at 120° C. for 3 hours. The reaction mixture was cooled to ambient temperature and diluted with EtOAc and 1 MHCl/brine (1/1) and the layers separated. The aqueous layer was extracted with EtOAc (×2) and the combined organic extracts washed with brine (×2), dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography (ISCO Companion™, 120 g column, eluting with 0 to 40% EtOAc/Petroleum Ether, dry loaded) to give the sub-title product as a yellow solid (815 mg, 71% Yield). 1H NMR (400.0 MHz, DMSO) δ 6.88 (dd, 1H), 7.00 (br s, 2H), 7.11-7.11 (m, 1H), 7.17 (d, 1H), 7.25 (t, 1H), 8.12 (s, 1H) and 9.77 (s, 1H) ppm; MS (ES+) 292.0.

Provenance & Evidence