HCID 10862504, compound → HCID 54597238, compound

Participants

Reaction Conditions

Reaction Steps

tributyl-[(E)-1-fluoro-2-phenyl-vinyl]stannane (190 mg, 0.4621 mmol), 3-bromo-5-(4-isopropylsulfonylphenyl)pyrazin-2-amine (164.6 mg, 0.4621 mmol), palladium (9.835 mg, 0.09242 mmol) and cuprous iodide (83.61 mg, 14.85 μL, 0.4390 mmol) were combined in THF (5 mL) and was stirred at 80° C. for 1 hour under microwave conditions. After this time the mixture was filtered over celite, concentrated in vacuo, and the residue was triturated twice in petroleum ether and dried. This material was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 μM, 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, and freeze-dried to give the title compound (44 mg, 18.92% Yield). H1 NMR (400.0 MHz, DMSO) H NMR (400.0 MHz, DMSO) δ 1.16-1.19 (d, 6H), 3.45 (m, 1H), 6.88 (d, J=40.7 Hz, 1H), 6.96 (s, 2H), 7.35 (t, J=7.4 Hz, 1H), 7.46 (t, J=7.6 Hz, 2H), 7.73 (d, J=7.5 Hz, 2H), 7.92 (d, J=8.5 Hz, 2H), 8.32 (d, J=8.5 Hz, 2H) and 8.82 (s, 1H) ppm. MS (ES+) 398.0

Provenance & Evidence