Trifluoroacetic acid → HCID 25094494, compound

Participants

Reaction Steps

To 2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-ol (50 mg, 0.15 mmol) in DMF (3 mL) was added 4 angstrom molecular sieves (2 g), tert-butyl 2-bromoethylcarbamate (40 mg, 0.18 mmol), t-butylammonium iodide (3 mg) and cesium hydroxide hydrate (50 mg, 0.30 mmol). The reaction mixture was stirred overnight, then dilute with EtOAc/H2O (10 mL/10 mL). The aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered, and concentrated to give crude, N-Boc-protected product, to which was added DCM (1 mL) and TFA (1 mL). This mixture was stirred for 30 minutes and then concentrated. The residue was purified by silica gel chromatography, eluting with DCM/MeOH/NH4OH (10:1:0.1) to provide the desired product (20 mg). APCI (+) m/z 379.2 (M+1) detected.

Provenance & Evidence