Thiophenol → HCID 54596502, compound

Participants

Reaction Conditions

Reaction Steps

Benzenethiol (73.29 mg, 68.30 μL, 0.6652 mmol) was added slowly to a suspension of sodium hydride (60% dispersion in mineral oil) (19.16 mg, 21.29 μL, 0.7983 mmol) in anhydrous DMF (1.300 mL) at 0° C. The reaction mixture was stirred until the evolution of H2 ceased. 3-Amino-6-bromo-N-phenyl-pyrazine-2-carboxamide (130 mg, 0.4435 mmol) was added followed by Cu2O (15.87 mg, 0.1109 mmol) and reaction mixture heated to 100° C. for 4 hours. The reaction mixture was cooled to ambient temperature and quenched with crushed ice. The aqueous layer was extracted with EtOAc (×3) and the combined organic extracts washed with ammonium hydroxide (×1), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 mM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected, passed through a sodium bicarbonate cartridge and freeze-dried to give the title compound as a yellow solid (52 mg, 31% Yield). 1H NMR (400.0 MHz, DMSO) δ 7.19-7.23 (m, 1H), 7.43-7.54 (m, 7H), 7.77-7.80 (m, 4H), 8.37 (s, 1H) and 10.15 (s, 1H) ppm; MS (ES+) 322.99.

Provenance & Evidence