4-Fluorophenol → HCID 57960805, compound

Participants

Reaction Steps

A mixture of 1-(4-bromo-phenyl)-3-cyclobutyl-imidazo[1,5-a]pyrazin-8-ylamine (30.0 mg, 0.0874 mmol), 4-fluorophenol (29.4 mg, 0.262 mmol), copper(I) iodide (5 mg, 0.03 mmol), Cs2CO3 (114 mg, 0.350 mmol), N,N-dimethylglycine hydrochloride (10 mg, 0.08 mmol) and 5:1 dioxane:DMF (1 mL) was microwaved at 120° C. for 4 h (CEM; PowerMAX). The mixture was filtered through a syringe filter pad to remove any solid particles, then concentrated in vacuo. DMF (1 mL) was added to bring the mixture to a homogeneous solution, and Gilson HPLC was used to purify. The fractions containing the product were passed through a benzene-sulfonic acid SPE cartridge, washed with MeOH (10 mL), and flushed out using 2M NH3 in MeOH. The material was concentrated in vacuo to afford the title compound as a yellow solid. 1H NMR (400 MHz, CDCl3): δ=1.99-2.09 (m, 1H), 2.11-2.24 (m, 1H), 2.45-2.55 (m, 2H), 2.58-2.69 (m, 2H), 3.77-3.87 (m, 1H), 5.12 (br. s., 2H), 7.01-7.13 (m, 8H), 7.61-7.65 (m, 2H). MS (ES+): m/z 374.98 (100) [MH+]. HPLC: tR=2.55 min (ZQ3, polar—5 min).

Provenance & Evidence