Potassium Hydroxide → Furo[3,2-c]pyridin-7-ol

Participants

Reaction Conditions

Reaction Steps

A mixture of 7-bromofuro[3,2-c]pyridine (9.15 g, 46.2 mmol), potassium hydroxide (7.78 g, 139 mmol), Pd2(dba)3 (0.02 eq) and 2-di-tert-butylphosphino-3,4,5,6-tetramethyl-2′,4′,6′-triisopropyl-1,1′-biphenyl (0.08 eq) in H2O (22.5 mL) and 1,4-dioxane (22.5 mL) was vigorously stirred at 100° C. overnight. LC-MS showed completion of the reaction. The reaction mixture was washed with DCM (3×30 mL). The aqueous layer was neutralized and concentrated by freeze dryer. The resulting solid was washed with massive amount of acetone to give the title compound as a white solid (6.2 g, 81% yield). 1H NMR (DMSO-d6, 400 MHz): δ=7.05 (d, J=2.0 Hz, 1H), 8.04 (s, 1H), 8.06 (d, J=2.2 Hz, 1H), 8.44 (s, 1H). MS (ES+): m/z=136.15 [MH+].

Provenance & Evidence