Toluene → HCID 20567052, compound

Participants

Reaction Conditions

Reaction Steps

(4-Bromophenyl)boronic acid (100 mg, 0.498 mmol) and 5-bromopyrazin-2-amine (173 mg, 0.996 mmol) were added to a 5 mL sealable vial equipped with a stir bar. To this vial was added toluene (1.5 mL), ethanol (1.5 mL) and K2CO3(0.7 mL, 2 M). The solvent was sparged with argon for 10 min before adding Pd(PPh3)4 (17 mg, 0.004 mmol), the vial sealed and the mixture stirred at 50° Celsius for 15 hours. The reaction was cooled to rt and then diluted with ethyl acetate (50 mL) and water (50 mL) and the layers separated. The aqueous layer was further extracted with ethyl acetate (3×50 mL). The combined organic extracts were dried with Na2SO4 and concentrated to dryness. The crude material was purified FCC to give 5-(4-bromophenyl)pyrazin-2-amine. 1H NMR (500 MHz, CDCl3) δ 8.52-8.31 (d, J=1.5, 1H), 8.08-7.95 (d, J=1.6, 1H), 7.86-7.71 (d, J=8.4, 2H), 7.63-7.49 (d, J=8.6, 2H), 4.70 (s, 2H).

Provenance & Evidence