Sodium Carbonate → 2-Chloro-6-(4-(isopropylsulfonyl)phenyl)pyrazine

Participants

Reaction Steps

A mixture of 2,6-dichloropyrazine (653.1 mg, 4.384 mmol), (4-isopropylsulfonylphenyl)boronic acid (500 mg, 2.192 mmol), Pd(PPh3)4 (126.6 mg, 0.1096 mmol) and Na2CO3 (2.192 mL of 2 M, 4.384 mmol) in ethanol (500.0 μL) and toluene (7.500 mL) was heated at reflux for 72 hours. The reaction mixture was cooled to ambient temperature and diluted with water and DCM. The layers were separated and the aqueous layer was extracted with DCM (×3). The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (ISCO Companion™, 40 g column, eluting with 0 to 40% EtOAc/Petroleum Ether) to give the sub-title product as a white solid (321 mg, 49% Yield). 1H NMR (400.0 MHz, DMSO) δ 9.41 (s, 1H), 8.88 (s, 1H), 8.41 (d, 2H), 8.03 (d, 2H), 3.54-3.49 (m, 1H) and 1.19 (d, 6H) ppm; MS (ES+) 297.1

Provenance & Evidence