Hydrogen Bromide → HCID 86667789, compound

Participants

Reaction Steps

5-Isopropylsulfonylpyrazin-2-amine was added to a rapidly stirring mixture of hydrobromic acid in acetic acid (2.150 mL of 45% w/v, 11.96 mmol) and acetic acid (649.6 μL) at 0° C. followed by the slow addition of bromine (1.433 g, 462.0 μL, 8.967 mmol) dropwise over a 10 minutes. A solution of sodium nitrite (515.5 mg, 237.8 μL, 7.472 mmol) in water (2.275 mL) was added dropwise over 10 minutes and the reaction mixture was stirred at 0° C. for a further 15 minutes. The reaction mixture was basified with 16 mL of saturated aqueous NaHCO3 at 0° C. and 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 100% EtOAc/Petrol, loaded in DCM) to give the sub-title product as a cream solid (349 mg, 44% Yield). 1H NMR (400.0 MHz, DMSO) δ 1.24 (d, 6H), 3.69 (sept, 1H). 9.04 (s, 1H) and 9.17 (s, 1H); MS (ES+) 267.0.

Provenance & Evidence