7,12-Dimethylbenz(a)anthracene → 6-(3-amino-2-fluoropropyl)-9-chloro[1,2,4]triazolo[3,4-a]isoquinolin-3(2H)-one

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Reaction Conditions

Reaction Steps

6-[3-(allylamino)-2-fluoropropyl]-9-chloro[1,2,4]triazolo[3,4-a]isoquinolin-3(2H)-one (6-4)(18 mg, 0.054 mmol, 1.0 equiv) and DMBA (25.2 mg, 0.16 mmol, 3.0equiv) and tetrakis(triphenylphosphine)palladium(0) (3 mg, 2.60 μmol, 0.05 equiv) were suspended in ClCH2CH2Cl (1 mL). The resulted yellow suspension was heated at 50° C. LCMS at 5 hours showed mostly product. The crude was purified with reverse phase HPLC H2O/CH3CN gradient w/0.1% TFA present) to afford the pure product (6-5). 1H NMR (500 MHz, CD3OD) δ 8.26 (d, 1H, J=2.3 Hz), 7.88 (d, 1H, J=8.5 Hz), 7.72 (dd, 1H, J=8.5, 2.3 Hz), 7.61 (s, 1H), 5.19-4.94 (dm, 1H, J=50.0 Hz), 3.52-3.33 (m, ˜4H, overlap w/solvent peak). LRMS m/z (M+H) 295.3 found, 295.1 required.

Provenance & Evidence