3-(2,6-Dichloro-4-pyridinyl)-5-methoxy-1H-pyrrolo[2,3-b]pyridine → HCID 178493709, Verbindung

Beteiligte Stoffe

Reaktionsschritte

A mixture of Example 149e (43.9 mg, 0.146 mmol) and trans-4-aminocyclohexanol (0.337 g, 2.92 mmol) in acetonitrile (1.5 mL) and EtOH (1.5 mL) was heated at 190° C. for 3 hours in a Biotage microwave reactor. The solvent was evaporated. The residue was treated with 5% citric acid and brine, and extracted with EtOAc (2×). The combined organic layers were dried over MgSO4, filtered, concentrated, and purified on a 12 g column using the ISCO Companion flash system eluting with CH2Cl2/EtOAc (5:95) to 100% EtOAc to give 22.0 mg of the title compound. 1H NMR (500 MHz, DMSO-d6) ppm 1.15-1.33 (m, 3H), 1.84 (d, J=10.98 Hz, 2H), 1.96 (d, J=11.29 Hz, 2H), 2.07 (m, 1H), 3.40 (m, 1H), 3.59 (m, 1H), 3.89 (s, 3H), 6.76-6.90 (m, 2H), 7.78 (d, J=2.75 Hz, 1H), 8.07 (dd, J=6.71, 2.75 Hz, 2H), 12.03 (s, 1H). MS (APCI+) m/z 373.4 (M+H)+.

Herkunft & Nachweise