Hydrogen Peroxide → 8-Fluoro-1-{[(1R,2R,4R)-4-hydroxy-2-methylcyclohexyl]amino}-5H-pyrido[4,3-b]indole-4-carboxamide

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Reaction Conditions

Reaction Steps

To a stirred solution of 8-fluoro-1-{[(1R,2R,4R)-4-hydroxy-2-methylcyclohexyl]amino}-5H-pyrido[4,3-b]indole-4-carbonitrile (4.8 g, 14.2 mmol) in DMSO (100 mL) were added hydrogen peroxide (30%, 14.5 mL, 142 mmol) and potassium carbonate (10.6 g, 77 mmol). The reaction mixture was heated to 70° C. overnight, cooled to room temperature, treated with brine, and extracted with EtOAc (×3). The combined organics were dried, concentrated, and purified by flash chromatography to afford the title compound. 1H NMR (600 MHz, CD3OD) δ 8.43 (s, 1H); 7.94 (dd, 1H); 7.57 (dd, 1H); 7.13 (dt, 1H); 3.98 (m, 1H); 3.67 (m, 1H); 1.22-2.12 (series of m, 7H); 1.01 (d, 3H). LRMS (APCI) calc'd for (C19H21FN4O2) [M+H]+, 357.2. found 357.1.

Provenance & Evidence