Hydrochloric Acid → 3-(2-{[6-chloro-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-2-yl]amino}ethyl)phenol

Participants

Reaction Conditions

Reaction Steps

A mixture of Example 7a (75.0 mg, 0.186 mmol), 3-(2-aminoethyl)phenol.HCl (0.250 g, 1.44 mmol), and diisopropylethylamine (0.52 mL, 2.97 mmol) in acetonitrile (0.6 mL) was heated in a Biotage microwave reactor at 160° C. for 30 minutes. The reaction mixture was treated with 20% brine and extracted with EtOAc (2×). The combined organic layers were washed with 20% brine, dried over MgSO4, filtered, and concentrated. The crude was dissolved in dioxane (1.3 mL) and treated with 20% NaOH (0.12 mL). The mixture was heated at 60° C. for 1 hour and concentrated. The residue was treated with water, sonicated, filtered, washed with water, and dried. The crude material was purified on a 4 g column using the ISCO Companion flash system eluting with CH2Cl2/MeOH (97:3 to 90:10) to give 5.5 mg of the title compound. 1H NMR (500 MHz, DMSO-d6) ppm 2.77 (t, J=7.32 Hz, 2H), 3.46 (t, J=6.87 Hz, 2H), 6.61 (d, J=7.93 Hz, 1H), 6.65-6.74 (m, 2H), 6.87 (s, 1H), 6.89-6.98 (m, 2H), 7.09 (t, J=7.78 Hz, 1H), 7.21 (dd, J=7.93, 4.88 Hz, 1H), 8.14 (d, J=2.75 Hz, 1H), 8.25-8.35 (m, 2H), 9.27 (s, 1H), 12.16 (s, 1H). MS (DCI+) m/z 365.0 (M+H)+.

Provenance & Evidence