Cesium carbonate → 6-(3-Hydroxyazetidin-1-yl)-1-methyl-1H-pyrrolo[3,2-b]pyridine-5-carbonitrile

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Reaction Conditions

Reaction Steps

6-Bromo-1-methyl-1H-pyrrolo[3,2-b]pyridine-5-carbonitrile (4.27 g, 18.1 mmol), azetidin-3-ol (2.36 g, 18.1 mmol), Xantphos (1.05 g, 1.81 mmol), Pd(OAc)2 (0.406 g, 1.81 mmol) and cesium carbonate (11.8 g, 36.2 mmol) in dioxane (100 mL) were combined in a flask to give an orange suspension. The flask was purged with N2, sealed, and heated to 90° C. for 3 hours. The crude material was diluted with EtOAc (25 mL) and filtered through a pad of Celite. The filtrate was washed with saturated aqueous NH4Cl (3×). The combined organic layers were dried over MgSO4, filtered, and concentrated. The crude product was loaded onto a silica gel cartridge (ISCO®, 120 g) and eluted using an EtOAc/hexane gradient. The product was collected and concentrated in vacuo to afford the title compound as a yellow solid (2.8 g, 67%). ESI-MS m/z [M+H]+ calc'd for C12H12N4O, 229; found 229.

Provenance & Evidence