Styrene → HCID 24758844, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-cyclobutyl-1-iodoimidazo[1,5-a]pyrazin-8-amine (50 mg, 0.159 mmol), styrene (0.022 mL, 0.191 mmol) and triethylamine (0.044 mL, 0.318 mmol) in DMF (3.0 mL) was degassed three times, charged with tetrakis(triphenylphosphine)palladium (0) (18 mg, 0.0159 mmol) degassed twice more and then heated at 75° C. for 16 h. The reaction mixture was then concentrated in vacuo dissolved in MeOH/CH3CN (1:1)(4 mL) and was filtered through a 0.45 μM fritted autovial prior to purification via mass directed preparative HPLC which afforded the title compound. 1H NMR (DMSO-d6, 400 MHz) δ 1.87-1.99 (m, 1H), 2.02-2.17 (m, 1H), 2.37-2.47 (m, 4H), 3.18 (s, 2H), 3.83-3.94 (m, 1H), 6.94 (d, J=4.9 Hz, 1H), 7.25 (t, J=7.33 Hz, 1H), 7.32-7.40 (m, 3H), 7.45 (d, J=15.5 Hz, 1H), 7.63 (d, J=15.45 Hz, 1H), 7.73 (d, J=7.46 Hz, 2H); MS (ES+): m/z 291.15 [MH30 ].

Provenance & Evidence