Trifluoromethanesulfonic acid → 7-(2-Aminopyrimidin-5-yl)-1-{[(1r)-1-cyclopropyl-2,2,2-trifluoroethyl]amino}-8-iodo-5h-pyrido[4,3-b]indole-4-carboxamide

Participants

Reaction Steps

To a stirred slurry of 7-(2-aminopyrimidin-5-yl)-1-{[(1R)-1-cyclopropyl-2,2,2-trifluoroethyl]amino}-5H-pyrido[4,3-b]indole-4-carboxamide (60 mg, 0.14 mmol) and bis(pyridine)iodonium tetrafluoroborate (152 mg, 0.41 mmol) in DCM (2.5 mL) was added trifluoromethanesulfonic acid (0.11 mL, 1.2 mmol). The reaction mixture was left to stir for 2 d, treated with additional bis(pyridine)iodonium tetrafluoroborate (152 mg, 0.41 mmol) and trifluoromethanesulfonic acid (0.07 mL, 0.8 mmol), and left to stir for 6 h. The mixture was diluted with DCM and treated with sodium bicarbonate solution. The mixture was extracted with EtOAc, and the combined organics were washed with brine, dried (sodium sulfate), concentrated, and purified by flash chromatography to afford the title compound. 1H NMR (600 MHz, CD3SOCD3) δ 11.78 (s, 1H); 9.02 (s, 1H), 8.51 (s, 1H); 8.23 (s, 2H); 7.92 (br s, 1H); 7.70 (s, 1H); 7.78 (br s, 1H); 7.77 (d, 1H); 6.80 (s, 2H); 4.87 (m, 1H); 1.58 (m, 1H); 0.73 (m, 1H); 0.62 (m, 1H); 0.54 (m, 1H); 0.32 (m, 1H). LRMS (APCI) calc'd for (C21H17IF3N7O) [M+H]+, 568.0. found 568.0.

Provenance & Evidence