Triethylamine → HCID 54670657, compound

Participants

Reaction Conditions

Reaction Steps

3-Ethynylphenol (187.0 mg, 103.7 μL, 1.583 mmol) was added to a solution of 3-bromo-5-(4-(isopropylsulfonyl)phenyl)pyrazin-2-amine (500 mg, 1.319 mmol), Et3N (1.335 g, 1.839 mL, 13.19 mmol), Copper(I) iodide (30.15 mg, 0.1583 mmol) and Pd(PPh3)4 (76.21 mg, 0.06595 mmol) in DMF (5 mL) and the resulting solution heated at 100° C. for 90 minutes in a sealed tube. The reaction mixture was cooled to ambient temperature and diluted with EtOAc and 1MHCl/brine (1:1). The layers were separated and the aqueous layer was extracted with ethyl acetate (×2). The combined organics extracts were washed with brine, dried over (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography (ISCO Companion™, 40 g column, eluting with 0 to 100% EtOAc/Petroleum Ether) to give the title product as a yellow solid (352 mg, 68% Yield). 1H NMR (400.0 MHz, DMSO) δ 1.18 (d, 6H), 3.44 (sept, 1H), 6.87-6.90 (m, 1H), 7.13-7.15 (m, 3H), 7.19-7.21 (m, 1H), 7.27 (t, 1H), 7.90 (d, J=8.6 Hz, 2H), 8.24 (d, J=8.6 Hz, 2H), 8.75 (s, 1H) and 9.77 (s, 1H) ppm; MS (ES+) 394.2.

Provenance & Evidence